UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, DC 20549

SCHEDULE 14A

(RULE 14a-101)
SCHEDULE 14A INFORMATION
Proxy Statement Pursuant to Section 14(a) of the Securities
Exchange Act of 1934

Filed by the Registrant ☒

Filed by a Party other than the Registrant ☐

Check the appropriate box:

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Preliminary Proxy Statement

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Confidential, for Use of the Commission Only (as permitted by Rule ~~14a-6I(2)~~14a-6(e)(2))

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Definitive Proxy Statement

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Definitive Additional Materials

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Soliciting Material Pursuant to ~~§240.14a-12-6I(2))~~§240.14a-12

22nd Century Group, Inc.

(Name of Registrant as Specified in its Charter)

(Name of Person(s) Filing Proxy Statement, if Other Than the Registrant)

Payment of Filing Fee (Check the appropriate box):

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No fee required.

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Fee paid previously with preliminary materials.

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Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11.

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~~500 Seneca Street, Suite 508,~~To the Shareholders of 22nd Century Group, Inc.:

In the 5 months that I have been the CEO and Chairman of your company, I have gotten to know several of you on a first name basis and have received comments and feedback from many others. For those of you who don’t yet know me, one thing you will come to find is that I am a believer in candid and straightforward communication. To the shareholders of this company, that means giving you the information you deserve to have in making your investment decisions, including our ups and downs, wins and losses. In short, I strive to communicate the business facts I would want to know in your shoes.

Some of you have shared your perspectives with me on why you chose to become shareholders in the first place and why you still believe in the future of 22nd Century: our unique position in the industry, our disruptive potential, and our mission to reduce harm from nicotine consumption. Others have shared frustrations and disappointment at unmet expectations. For all your feedback, and speaking on behalf of the entire management team and the Board of Directors, let me say: We have heard you loud and clear.

A Year of Transition

So much has changed in the past 5 months at 22nd Century it’s hard to know where to begin. Our divestiture of the GVB hemp/cannabis business was a great weight lifted from the company, both in terms of cost and attention drain. We closed our headquarters in Buffalo ~~New York 14204~~and our lab facilities in Maryland and consolidated all operations to our factory in North Carolina. We eliminated the second shift at the North Carolina facility and consolidated production to one shift for a substantial productivity gain.

Most importantly, we have firmly returned our focus 100% to our tobacco business. We are fully dedicated to making 22nd Century a profitable, cash positive, NASDAQ listed company with a strong foothold in our industry sector, and once again centered in our mission of using our patented biotechnology for creation of products that address the harms of nicotine addiction and commercializing those products. In pursuing this mission, our priority is, “What is good for the future of company, comes first.”

As for the management team and Board of Directors, the changes are no less dramatic. All retention, severance, and other employment agreements have been eliminated. Bonus compensation and equity awards in the absence of profits are gone. Board compensation is suspended until after the 2024 Annual Shareholder Meeting. Spending on consultants and advisors has been terminated except only those few that are mission critical.

Drive to Breakeven

Throughout 2023, our hemp/cannabis segment was the largest source of cash burn as unfunded overhead drove some of our largest losses. Additionally, companies that have operations around cannabis have what I call a “cannabis tax” on the entire business. This tax comes in the form of a cost premium on just about every cost that the entire company incurs, such as insurance and financing. Therefore, selling the GVB business not only eliminated a substantial portion of our cash drain, but also allows us to lower costs in our core tobacco business going forward.

In 2024 we are on a drive to financial breakeven for the first time in the company’s history. The cost reductions mentioned above are part of closing that gap, as well as raising prices on unprofitable product lines. In addition, we are working on new profitable revenue opportunities for both VLN® and the contract manufacturing or CMO business to drive higher gross profits to achieve our breakeven point as soon as possible.

Renewed Focus on VLN®

Our flagship product VLN® means Very Low Nicotine. We believe our trademarked brand, VLN®, serves the same purpose for nicotine harm reduction from cigarettes as decaf coffee does for regular coffee. If anyone has told you that you need to cut back, our VLN® offers a compelling alternative.

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We are THE brand in the marketplace, representing the only very low nicotine cigarette with 95% less nicotine than a standard cigarette.

It is common knowledge that a majority of smokers want to quit and they are trying to quit consistently and unsuccessfully year after year. They need help to smoke less, they need tools such as our VLN®. We are the first and only company that has an FDA authorization to market a combustible cigarette, our VLN®, using certain reduced nicotine exposure claims, i.e., VLN®helps you smoke less. We are well protected from an intellectual property standpoint. We have a tool, our VLN® cigarette, that we believe smokers will want to use in their fight against nicotine.

The mission to drive reduced nicotine harm for smokers and acquire customers who want to reduce their nicotine intake is a simple math equation. The simple math is, from a nicotine content perspective, one pack of 20 VLN® cigarettes is approximately equal to one single cigarette of any standard cigarette brand.

One key to driving revenue growth for VLN® is to increase brand awareness. In early 2024, we began an engagement with a highly successful marketing firm with a proven track record in reshaping brand identities. We are determined to reach a previously untapped customer base to help them smoke less.

We are working on enhanced branding, leveraging and increasing our distribution and launching new marketing for our VLN® cigarettes in 2024 in an effort to drive customer awareness and customer success. The success of VLN® is, and continues to be, our highest priority in driving shareholder value.

Growth in the Contract Manufacturing (CMO) Business

We are pursuing several new CMO opportunities in our mission to drive profitable revenue. These opportunities could profitably counter the volume from contracts that we are offloading where we lose money. The shift in product mix of CMO volume, along with increases from new contracts, continue to help our manufacturing overhead absorption so the more volume we run through the factory on the same overhead cost, the lower our cost per carton will be on all the existing products including VLN®. These changes will promote revenue growth and gross margin improvement, which are integral to eliminating cash burn for our organization.

Refreshed outlook

We are invigorated and excited with the start of 2024 and progress made to date. As I write this, the leaders of every business function in the company have joined me in an intensive and ongoing exercise to chart a collective and definitive strategy toward profitability and restoration of shareholder value. The effect this is having throughout the company is palpable, with renewed employee engagement and enthusiasm at every level. We are totally reshaping 22nd Century with the goal of becoming a profitable, cash positive NASDAQ listed company with a strong foothold in the tobacco space focused on nicotine harm reduction.

I would like to thank our shareholders, customers, end users, suppliers and employees who keep us motivated to drive 22nd Century forward.

Lawrence Firestone

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321 Farmington Road, Mocksville, North Carolina 27028

Notice of ~~Special~~2024 Annual Meeting of Stockholders and Proxy Statement

TO THE HOLDERS OF COMMON STOCK:

PLEASE TAKE NOTICE that ~~a Special~~the Annual Meeting of stockholders of 22nd Century Group, Inc. (the “Company”) will be held at 11988 El Camino Real, Suite 400, San Diego, CA 92130 on ~~January, 24,~~Friday, June 28, 2024, beginning at 11:00 ~~A.M,~~A.M., Eastern Time.

The meeting will be held for the following purposes:

To approve an amendment to ~~our~~the Company’s Amended and Restated Articles of Incorporation ~~as amended,~~ to ~~effect a reverse stock split~~declassify the Board of ~~our outstanding common stock at a ratio between 1-for-2 and 1-for-16, to be determined at the discretion of our board of directors~~Directors (the ~~“Reverse Split”~~“Charter Amendment”)~~, for the purpose of complying with the Nasdaq Listing Rules, subject to the Board’s discretion to abandon such amendment~~ (Proposal 1).

~~To approve an amendment~~If the Charter Amendment is approved, to ~~our Articles~~elect four (4) directors to the Board of ~~Incorporation, as amended,~~Directors to ~~increase~~serve until the ~~number of authorized shares of common stock from sixty-six million, six hundred sixty-six thousand six hundred sixty-seven (66,666,667) shares to two hundred fifty million (250,000,000)~~2025 Annual Meeting and, in each instance, until their respective successors have been elected and qualified (Proposal 2).

If the Charter Amendment is not approved, to elect as director the one (1) director nominee named in the attached proxy statement as a Class I director to serve for a three-year period until the Annual Meeting of stockholders in the year 2027 until his respective successor has been elected and qualified (Proposal 3).

To approve an advisory resolution approving executive compensation for fiscal year 2023 (Proposal 4).

To approve the ~~issuance~~amendment and restatement of the 22nd Century Group, Inc. 2021 Omnibus Incentive Plan which shall increase the number of shares ~~of common stock~~authorized for issuance by five million (5,000,000) (Proposal 5).

To approve the Warrants dated April 9, 2024 and the shares issuable upon exercise of the warrants ~~to purchase common stock (the “Inducement Warrants”) issued to accredited investors~~ pursuant to ~~warrant inducement agreements in accordance with the terms~~Rule 5635(d) of the ~~Inducement Warrants, as required by and in accordance with~~ Nasdaq ~~Listing Rules~~Stock Market (Proposal 3)6).

4.7.

To approve the Voluntary Conversion Option in the Debentures dated March 3, 2023, as amended December 22, 2023, pursuant to Rules 5635(b) and 5635(d) of the Nasdaq Stock Market (Proposal 7).

To ratify the appointment of Freed Maxick CPAs, P.C. as our independent registered public accountants for fiscal year 2024 (Proposal 8).

To approve the adjournment of the meeting, if necessary or advisable, to solicit additional proxies in favor of ~~Proposals 1, 2 and/~~the Charter Amendment (Proposal 1), the amendment and restatement of our 2021 Omnibus Incentive Plan (Proposal 5), the approval of the Warrants (Proposal 6) or 3the approval of the Voluntary Conversion Option (Proposal 4)7).

The stockholders of record at the close of business on ~~December 6, 2023~~April 29, 2024 will be entitled to vote at the ~~Special~~Annual Meeting.

	MEETING INFORMATION:
	DATE: ~~January, 24,~~Friday, June 28, 2024
	TIME: 11:00 A.M., Eastern Time
	PLACE: The meeting will be held at 11988 El Camino Real, Suite 400, San Diego, CA 92130.
	HOW TO VOTE:
	Your vote is important. You are eligible to vote if you were a stockholder of record at the close of business on ~~December 6, 2023.~~April 29, 2024.
				BY INTERNET www.proxyvote.com
				BY PHONE Call 1.800.690.6903
				BY MAIL Complete, sign and return by free post
				IN PERSON Attend the ~~Special~~Annual Meeting

By Order of the Board of Directors,

Lawrence D. Firestone
Chairman and Chief Executive Officer
Dated: ~~December 11, 2023~~April 29, 2024

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Table of Contents

	Notice of Annual Meeting					iii
	Table of Contents					iv
	Proxy Summary					1
	PROXY SUMMARY					1
	Voting Matters					1
	Frequently Asked Questions Regarding ~~Special~~Annual Meeting Procedures					12
	~~Proposal One:~~PROPOSAL NO. 1: Approval of an Amendment to the ~~Amendment To Effect The Reverse Stock Split~~Company’s Amended and Restated Articles of Incorporation to declassify the Board of Directors (the “Charter Amendment”)					46
	PROPOSAL NO. 2: If Proposal Two: Approval of an Increase in the Number of Shares of Authorized Common Stock from Sixty-Six Million Six Hundred Sixty-Six Thousand Sixty Hundred Sixty-Seven (66,666,667) to Two Hundred Fifty Million (250,000,000)No. 1 Is Approved, To Elect Four Directors					127
	Nominees and Director Qualifications					7
	Commitment to Corporate Governance					9
	Board of Directors					9
	Independent Directors					9
	Board Leadership Structure and the Role of the Board in Oversight of Risk Management					9
	Stockholder Communications with the Board					9
	Meetings of Board of Directors					10
	Executive Sessions of Independent Directors					10
	Corporate Governance Guidelines					10
	Standing Committees					10
	Code of Business Conduct and Corporate Ethics					11
	Insider Trading Policy					11
	Board Diversity Matrix					12
	Compensation of Directors					12
	Elements of 2023 Non-Employee Director Compensation					12
	Non-Employee Director Compensation for 2023					14
	PROPOSAL NO. 3: If Proposal ~~Three:~~No. 1 Is Not Approved, Elect One Class I Director					15
	PROPOSAL NO. 4: Advisory Approval on the Company’s 2023 Executive Compensation					16
	Compensation Committee Interlocks and Insider Participation					21
	PROPOSAL NO. 5: Approval of the Amendment and Restatement of the 22nd Century Group, Inc. 2021 Omnibus Incentive Plan					27
	Updated Share Information, Authorized Shares and Stock Price					27
	Summary of the Terms of the Plan					27
	Purpose and Effective Date					28
	Administration and Eligibility					28
	Types of Awards					28
	Stock Subject to the Plan and Award Limits					28
	Options					29
	Stock Appreciation Rights					29
	Performance and Stock Awards					29
	Incentive Awards					30
	Dividend Equivalents and Dividends					30
	Other Stock-Based Awards					30
	Minimum Vesting and Discretion to Accelerate					30

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	Performance Goals					31
	Effect of Termination of Employment or Service on Awards					31
	Transferability of Awards					31
	Adjustments					31
	Change of Control					32
	Termination and Amendment					34
	Cancellation, Disgorgement and Recoupment of Awards					34
	Repricing Prohibited					34
	Backdating Prohibited					34
	Foreign Participation					34
	Certain Federal Income Tax Consequences					35
	Stock Options					35
	Stock Appreciation Rights					35
	Restricted Stock					35
	Restricted Stock Units					36
	Performance Shares					36
	Performance Units					36
	Incentive Awards					37
	Dividend Equivalent Units					37
	Section 162(m) Limit on Deductibility of Compensation					37
	Code Sections 409A and 280G					37
	New Plan Benefits					37
	Equity Compensation Plan Information					38
	PROPOSAL NO. 6: Approval of the Issuance of the Shares of Common Stock upon Exercise of the ~~Inducement~~ Warrants ~~in Accordance with~~Dated April 9, 2024 Pursuant to Nasdaq Listing Rule 5635					1439
	~~Proposal Four:~~PROPOSAL NO. 7: Approval of the Voluntary Conversion Option in the Debentures Dated March 3, 2023, as Amended December 22, 2023, Pursuant to Rules 5635(B) and 5635(D) of the Nasdaq Stock Market					41
	PROPOSAL NO. 8: Ratification of Appointment of Freed Maxick CPAs, P.C. as the Company’s Independent Registered Public Accounting Firm for 2024					44
	PROPOSAL NO. 9: The Adjournment of the Meeting, if Necessary or Advisable, to Solicit Additional Proxies in Favor of Proposals 1, ~~2 or 3~~5, 6 Or 7					1645
	~~Beneficial Ownership~~BENEFICIAL OWNERSHIP					1746
	RELATED PARTY TRANSACTIONS					47
	Stockholder Proposals ~~for the 2024 Annual Meeting of Stockholders~~ and Communications with the Board of Directors					1848
	~~Important Notice Regarding the Internet Availability of Proxy Materials for the Special Meeting to be Held on January 24,~~IMPORTANT NOTICE REGARDING THE INTERNET AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL MEETING TO BE HELD ON JUNE 28, 2024					1848
	~~Other Matters~~OTHER MATTERS					1848

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PROXY SUMMARY

Here we present an overview of information that you will find throughout this proxy statement. As this is only a summary, we encourage you to read the entire proxy statement for more information about these topics prior to voting. This proxy statement and the accompanying form of proxy are first being sent or made available to our stockholders on or about April 29, 2024 in connection with the solicitation by our Board of Directors of proxies to be used at our 2024 Annual Meeting of Stockholders.

		Annual Meeting of Stockholders
		Time and Date:			11:00 A.M., Eastern Time, June 28, 2024
		Place:			The meeting will be held at the Company’s Corporate Headquarters, 11988 El Camino Real, Suite 400, San Diego, CA 92130.
		Record Date:			April 29, 2024

Voting Matters

The following table summarizes the proposals to be voted on prior to or at our 2024 Annual Meeting of Stockholders and the Board’s voting recommendations with respect to each proposal.

PROPOSAL	BOARD’S VOTING RECOMMENDATION	PAGE REFERENCE
Proposal 1: Approval of an amendment to the Company’s Amended and Restated Articles of Incorporation to declassify the Board of Directors (the “Charter Amendment”).	FOR	6
Proposal 2: If the Charter Amendment is approved, election of four directors to the Board of Directors to serve until the 2025 Annual Meeting.	FOR each nominee	7
Proposal 3: If the Charter Amendment is not approved, election of one director to the Board of Directors to serve until the 2027 Annual Meeting.	FOR each nominee	15
Proposal 4: Advisory Approval on the Company’s 2023 Executive Compensation.	FOR	16
Proposal 5: Approval of the Amendment and Restatement of the 2021 Omnibus Incentive Plan to increase the number of shares authorized by five million (5,000,000).	FOR	27
Proposal 6: Approval of the Warrants dated April 9, 2024 and the shares issuable upon exercise of the warrants pursuant to Rule 5635(d) of the Nasdaq Stock Market.	FOR	39
Proposal 7: Approval of the Voluntary Conversion Option in the Debentures dated March 3, 2023, as amended December 22, 2023, pursuant to Rules 5635(b) and 5635(d) of the Nasdaq Stock Market.	FOR	41
Proposal 8: Ratification of Appointment of Freed Maxick CPAs, P.C. as the Company’s Independent Registered Public Accounting Firm for 2024.	FOR	44
Proposal 9: Adjournment of the meeting, if necessary or advisable, to solicit additional proxies in favor of the Charter Amendment (Proposal 1), the amendment and restatement of our 2021 Omnibus Incentive Plan (Proposal 5), the approval of the Warrants (Proposal 6) or the approval of the Voluntary Conversion Option (Proposal 7).	FOR	45

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~~FREQUENTLY ASKED QUESTIONS REGARDING SPECIAL MEETING PROCEDURES~~Frequently Asked Questions Regarding Annual Meeting Procedures

Q: Why did I receive these materials?

The Board of Directors of 22nd Century Group, Inc. is soliciting proxies for the ~~Special~~2024 Annual Meeting of Stockholders ~~(Special~~(Annual Meeting) to be held on ~~January 24,~~June 28, 2024 ~~in person.~~to allow our stockholders to participate from any location that is convenient to them. You are receiving a proxy statement because you owned shares of our common stock on ~~December 6, 2023,~~April 29, 2024, and that entitles you to

vote at the meeting. By use of a proxy,

you can vote whether or not you attend the meeting. The proxy materials include this proxy statement for the ~~Special~~Annual Meeting, an annual report to stockholders, including our Annual Report on Form 10 K for the year ended December 31, 2023, and a proxy card or voting instruction form for the ~~Special~~Annual Meeting.

Q: What information is contained in this proxy statement?

The information in this proxy statement relates to the proposals to be voted on at the ~~Special~~Annual Meeting, the ~~approval~~voting process, our Board, the compensation of the Reverse Split (Proposal 1), the approval of an increase in the number of shares of authorized common stock from six hundred sixty-six thousand six hundred sixty-seven (66,666,667) shares to two hundred fifty million (250,000,000)directors and executive officers, and other

~~(Proposal 2),~~information that the ~~issuance of the shares of common stock upon exercise of the Inducement Warrants in accordance with Nasdaq rules (Proposal 3)~~Securities and ~~the adjournment of the meeting, if necessary or advisable,~~Exchange Commission requires us to ~~solicit additional proxies in favor of Proposals 1, 2 or 3 (Proposal 4).~~provide annually to our stockholders.

Q: Who is entitled to vote at the meeting?

Holders of common stock as of the close of business on the record date, ~~December 6, 2023,~~April 29, 2024, will receive notice of, and be eligible to vote at, the ~~Special~~Annual Meeting and at any adjournment or postponement of the Annual

~~the Special~~ Meeting. At the close of business on the record date, we had outstanding and entitled to vote a total of ~~43,779,056~~6,046,560 shares of common stock.

Q: How many votes do I have?

Each outstanding share of our common stock you owned as of the record date will be entitled to one

vote for each matter considered at the meeting. There is no cumulative voting.

Q: Who can attend the meeting?

Only persons with evidence of stock ownership as of the record date or who are invited guests of the Company, as determined by the Chairman of the Board or the executive officers of the Company, may attend and be admitted to the ~~Special~~Annual Meeting of the stockholders. Stockholders with evidence of stock ownership as of the record date may be accompanied by one guest. Photo identification may be required (a valid driver’s license, state identification or passport). If a stockholder’s shares are registered in the name of a broker, trust, bank or other nominee, ~~the~~

the stockholder must bring a proxy or a letter from that broker, trust, bank or other nominee or their most recent brokerage account statement that confirms that the stockholder was a beneficial owner of shares of common stock of the Company as of the record date. Since seating is limited, admission to the meeting will be on a first-come, first-served basis.

Cameras (including cell phones with photographic capabilities), recording devices and other electronic devices will not be permitted at the meeting.

Q: What constitutes a quorum?

The presence at the meeting, in person or by proxy, of the holders of one-third (33.33%) of the voting power

of common stock issued and outstanding on the record date will constitute a quorum, permitting the

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conduct of business at the meeting. Proxies received but marked as abstentions or broker non-votes, if any, will be included in the calculation of the number of

votes considered to be present at the meeting for

purposes of a quorum. If, however, such quorum shall not be present or represented at any meeting of the stockholders, a majority of the voting stock represented in person or by proxy may adjourn the meeting from time to time, without notice other than announcement at the meeting, until a quorum shall be present or represented.

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Q: How do I vote if I am a stockholder of record?

If your shares are registered directly in your name with our transfer agent, you are considered, with respect to those shares, the stockholder of record. As the stockholder of record, you have the right to vote in person at the meeting. If your shares are held in a brokerage account or by another nominee or trustee, you are considered the beneficial owner of shares held in street name. As the beneficial owner, you are also invited to attend the meeting. Since a beneficial owner is not the stockholder of record, you may not vote these shares in person at the meeting unless you obtain a “legal proxy” from your broker, trustee or nominee that holds your shares, giving you the right to vote the shares at the meeting. We urge you to vote by proxy even if you plan to attend the ~~Special~~Annual Meeting so that we will know as soon as possible that enough votes will be present for us to hold the meeting. If you attend the meeting, you may vote at the meeting and your proxy will not be counted. Our

Board of Directors has designated Lawrence D. Firestone, ~~our Chairman and CEO, Peter Ferola, General Counsel~~Chief Executive Officer, and Jonathan Staffeldt, ~~Vice~~

~~President and Deputy~~ General Counsel, and each or any of them or their designees, as proxies to vote the shares of common stock solicited on its behalf. You can vote by proxy by any of the following methods.

Voting by Telephone or Internet. If you are a stockholder of record, you may vote by proxy by telephone or internet. Proxies submitted by telephone or through the internet must be received by 11:59 p.m. EDT on ~~January 23,~~June 27, 2024. Please see the proxy card for instructions on how to vote by telephone or internet.

Voting by Proxy Card. Each stockholder receiving proxy materials by mail may vote by proxy using the accompanying proxy card. When you return a proxy card that is properly signed and completed, the shares represented by your proxy will be voted as you specify on the proxy card.

~~Voting in Person at the Special Meeting.~~ ~~Stockholders of record may attend the meeting and vote in person.~~

Q: How do I vote if I hold my shares in “street name”?

If you hold your shares in “street name,” we have supplied copies of our proxy materials for the ~~Special~~2024 Annual Meeting of Stockholders to the broker, trust, bank or other nominee holding your shares of record and they have the responsibility to send these proxy materials to you. You must either direct the broker, trust, bank or other

nominee as to how to vote your

shares, or obtain a proxy from the bank, broker or other nominee to vote at the meeting. Please refer to the voter instruction cards used by your broker, trust, bank or other nominee for specific instructions on methods of voting, including by telephone or using the internet.

Q: Can I change my vote?

Yes. You may revoke your proxy and change your vote at any time before the final vote at the meeting. If you are a stockholder of record, you may do this by: (i) signing and submitting a new proxy card with a later date; (ii) by voting by telephone, or by using the Internet — either of which must be completed by 11:59 p.m. Eastern Time on ~~January 23,~~June 27, 2024 (when your

latest telephone or Internet proxy is counted); or

(iii) by attending the ~~Special Meeting~~meeting and voting by ballot. Attending the ~~Special Meeting~~meeting alone will not revoke your proxy unless you specifically request your proxy to be revoked. If you hold shares through a bank or brokerage firm, you must contact that bank or firm directly to revoke any prior voting instructions.

Q: How are we soliciting this proxy?

We are soliciting this proxy on behalf of our Board of Directors and will pay all expenses associated with this solicitation. In addition to mailing these proxy

materials, certain of our officers and other employees may, without compensation other than their regular compensation, solicit proxies through further mailing

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or personal conversations, or by telephone, facsimile or other electronic means.

~~The Board of Directors has also retained Morrow Sodali as proxy solicitor. Proxy solicitation fees~~

~~related to this engagement include a $7,500 retainer plus costs and disbursements incurred by the firm.~~

We will also, upon request, reimburse brokers and other persons holding stock in their names, or in the

names of nominees, for their reasonable out-of-pocket expenses for forwarding proxy materials to the beneficial owners of our stock and to obtain proxies.

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Q: Will stockholders be asked to vote on any other matters?

To the knowledge of the Company and its management, stockholders will vote only on the matters described in this proxy statement. However, if any other matters properly come before the

meeting, the persons named as proxies for stockholders will vote on those matters in the manner they consider appropriate.

Q: What vote is required to approve each item?

The director nominees shall be elected by a plurality of the votes cast by the stockholders. The approval of Proposals 4 – 8 and the ~~Proposals 1, 3 and 4~~adjournment proposal require the number of votes cast in favor of the proposal to exceed the number of votes cast in opposition of the

proposal. The approval of the ~~Proposal 2, amendment~~

Charter Amendment to ~~our Articles~~declassify the Board of ~~Incorporation to increase the authorized number of shares of common stock,~~Directors (Proposal 1) requires the affirmative vote of the majority of the outstanding shares of our common stock.

Q: How are votes counted?

~~You~~For Proposals 2 and 3, you may vote “FOR” or “WITHHOLD” with respect to each of the nominees. In tabulating the voting results for the election of directors, only “FOR” votes are counted. If you elect to abstain in the election of directors, the abstention will not impact the outcome of the election. If Proposal 1 is approved, we will ignore the results of Proposal 3.

For the other proposals, you may vote “FOR,” “AGAINST” or “ABSTAIN.” An abstention is not considered a vote cast, and, therefore, are not counted and will not impact the outcome of the vote on any proposal other than ~~Proposal 2,~~ the approval of the ~~amendment~~Charter Amendment to ~~our Articles~~declassify the Board of ~~Incorporation to increase the authorized number of shares of common stock.~~Directors (Proposal 1).

If you hold your shares in “street name,” the Company has supplied copies of its proxy materials

for its ~~Special~~2024 Annual Meeting of stockholders to the broker, bank or other nominee holding your shares of record and they have the responsibility to send these proxy materials to you. Your broker, bank or other nominee that has not received voting instructions from you may not vote

on ~~Proposal 3 (Inducement Warrants) or Proposal 4 (Adjournment).~~any proposal other than the appointment of Freed as our independent registered certified public accounting firm for fiscal year 2024 and the adjournment proposal. These “broker non-votes” will be included in the calculation of the number of votes considered to be present at the meeting for purposes of determining a quorum but will not be considered in determining the number of votes necessary for approval of any of the proposals. Your broker, bank or other nominee is permitted to vote your shares on the ~~approval~~appointment of ~~the Reverse Split (Proposal 1)~~Freed as our independent registered certified public accounting firm and the ~~amendment to our Articles of Incorporation to increase the authorized number of shares of common stock (Proposal 2)~~adjournment proposal without receiving voting instructions from you.

Q: What should I do if I receive more than one set of voting materials?

You may receive more than one set of voting materials, including multiple copies of this proxy statement and multiple proxy cards or voting instruction cards. For example, if you hold your shares in more than one brokerage account, you may receive a separate voting instruction card for each brokerage account in which you hold shares. If you

are a stockholder of record and your shares are registered in more than one name, you will receive more than one proxy card. Please vote your shares applicable to each proxy card and voting instruction card that you receive.

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The SEC’s rules permit us to deliver a single set of ~~Special~~Annual Meeting materials to one address shared by two or more of our stockholders. This delivery method is referred to as “householding” and can result in significant cost savings. To take advantage of

this opportunity, we have delivered only one notice, proxy statement and annual report to multiple stockholders who share an address, unless we received contrary instructions from the impacted stockholders prior to the mailing date.

We agree to deliver promptly, upon written or oral request, a separate copy of the notice or ~~Special~~ Annual

Meeting materials, as requested, to any stockholder at the shared address to which a single copy of those documents was delivered. If you are currently a stockholder sharing an address with another stockholder and wish to receive only one copy of future proxy statements and annual reports for your household, please contact the Company at (716) 270-1523 or through www.xxiicentury.com/contact.

Q: Where can I find the voting results of the ~~Special~~Annual Meeting?

The Company will announce the preliminary voting results at the ~~Special~~Annual Meeting and release the final

results in a Form 8-K within four business days following the ~~Special Meeting.~~Annual Meeting

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~~PROPOSAL ONE: APPROVAL OF THE AMENDMENT~~
~~TO EFFECT THE REVERSE STOCK SPLIT~~

~~Overview~~

We are seeking stockholder approval to grant our board of directors discretionary authority to amend our Articles of Incorporation to effect a reverse split of all our outstanding shares of common stock, at a ratio between 1-for-2 and 1-for-16, to be determined at the discretion of our board of directors (the “Reverse Split”), for the purpose of complying with the Nasdaq Listing Rules, subject to the board’s discretion to abandon such amendment. If this Proposal 1 is approved, the board may decide not to effect the Reverse Split if it determines that it is not in the best interests of the Company to do so. The board does not currently intend to seek re-approval of the Reverse Split for any delay in implementing the Reverse Split unless twelve months has passed from the date of this Special Meeting (the “Authorized Period”). If the Board determines to implement the Reverse Split, it will become effective upon filing a Certificate of Amendment to the Articles of Incorporation with the Secretary of State of the State of Nevada or at such later date specified therein.

~~The text of the proposed Certificate of Amendment to our Articles of Incorporation to effect the Reverse Split is included as~~ ~~Appendix A~~ ~~to this Proxy Statement.~~

We are seeking stockholder approval of the Reverse Split because we do not intend to correspondingly decrease the number of our authorized shares of common stock. However, under Nevada law, the board would be permitted to affect a reverse stock split without stockholder approval if the number of authorized shares of common stock and the number of outstanding shares of common stock were correspondingly decreased.

~~Purpose of the Reverse Split~~

The primary purpose of the Reverse Split, if implemented, would be to potentially increase the market price of our common stock so that we can satisfy the minimum bid price rule in connection with Nasdaq continued listing requirements set forth in Nasdaq Listing Rule 5550(a)(2).

On November 7, 2023, we received a deficiency letter from Nasdaq indicating that, based on our closing bid price for the last 30 consecutive business days, we did not comply with the minimum bid price requirement of $1.00 per share, as set forth in Nasdaq Listing Rule 5550(a)(2). The notification had no immediate effect on the listing of our common stock on Nasdaq. In accordance with Nasdaq Listing Rule 5810(c)(3)(A), we have a grace period of 180 calendar days, or until May 6, 2024, to regain compliance with the minimum closing bid price requirement for continued listing. In order to regain compliance, the minimum closing bid price per share of our common stock must be at least $1.00 for a minimum of ten consecutive business days. In the event we do not regain compliance by May 6, 2024, we may be afforded an additional 180-day compliance period, provided we demonstrate that we meet all other applicable standards for continued listing on Nasdaq (except the bid price requirement), and provide written notice of our intention to cure the minimum bid price deficiency during the second grace period, by effecting a reverse stock split, if necessary. The Reverse Split is being proposed in order to possibly increase the market price of our common stock to satisfy the $1.00 minimum closing bid price required to try to avoid the delisting of our common stock from the Nasdaq, if necessary. In addition, a higher stock price, if the price does increase, may, among other things, increase the attractiveness of our common stock to the investment community.

As of December 6, 2023, the last reported closing price of our common stock was $0.24. A delisting of our common stock may materially and adversely affect a holder’s ability to dispose of, or to obtain accurate quotations as to the market value, of, our common stock. In addition, any delisting may cause our common stock to be subject to “penny stock” regulations promulgated by the SEC. Under such regulations, broker-dealers are required to, among other things, comply with disclosure and special suitability determinations prior to the sale of shares of common stock. If our common stock becomes subject to these regulations, the market price of our common stock and the liquidity thereof could be materially and adversely affected. Reducing the number of outstanding shares of our common stock should, absent other factors, increase the per share market price of our common stock, although we cannot provide any assurance that our minimum bid price would remain above the minimum bid price requirement of Nasdaq, or that this theoretical increase would indeed occur. Accordingly, we believe that approval of the amendment to our Articles of Incorporation to effect the Reverse Split in the board’s discretion is in the Company’s and our stockholders’ best interests.

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We also believe that the Reverse Split could enhance the appeal of our common stock to the financial community, including institutional investors, and the general investing public. We believe that a number of institutional investors and investment funds are reluctant to invest in lower-priced securities and that brokerage firms may be reluctant to recommend lower-priced stock to their clients, which may be due in part to a perception that lower-priced securities are less promising as investments, are less liquid in the event that an investor wishes to sell its shares, or are less likely to be followed by institutional securities research firms and therefore to have less third-party analysis of the Company available to investors. In addition, certain institutional investors or investment funds may be prohibited from buying stocks whose price is below a certain threshold. We believe that the reduction in the number of issued and outstanding shares of common stock caused by the Reverse Split, together with the anticipated increased stock price immediately following and resulting from the Reverse Split, may encourage interest and trading in our common stock and thus possibly promote greater liquidity for our stockholders, thereby resulting in a broader market for the common stock than that which currently exists.

Reducing the number of outstanding shares of our common stock through the Reverse Split is intended, absent other factors, to theoretically increase the per share market price of our common stock. However, other factors, such as our financial results, market conditions and the market perception of our business, may adversely affect the market price of our common stock. As a result, there can be no assurance that the Reverse Split, if completed, will result in the intended benefits described above, that the market price of our common stock will increase following the Reverse Split or that the market price of our common stock will not decrease in the future. Additionally, we cannot assure you that the market price per share of our common stock after the Reverse Split will increase in proportion to the reduction in the number of shares of our common stock outstanding before such Reverse Split. Accordingly, the total market capitalization of our common stock after the Reverse Split may be lower than the total market capitalization before the Reverse Split.

We cannot be sure that our share price will comply with the requirements for continued listing of our common stock on Nasdaq in the future or that we will comply with the other continued listing requirements. If our common stock loses its status on Nasdaq, we believe that our common stock would likely be eligible to be quoted on an inter-dealer electronic quotation and trading system operated by OTC Markets Group. These markets are generally considered to be less efficient than, and not as broad as, Nasdaq. Selling our common stock on these markets could be more difficult because smaller quantities of shares would likely be bought and sold, and transactions could be delayed. In addition, in the event that our common stock is delisted, broker-dealers have certain regulatory burdens imposed upon them, which may discourage them from effecting transactions in our common stock, further limiting the liquidity of our common stock. These factors could result in lower prices and larger spreads in the bid and ask prices for our common stock.

A delisting from Nasdaq and continued or further declines in our share price could also greatly impair our ability to raise additional necessary capital through equity or debt financing. There are risks associated with the Reverse Split, including that the Reverse Split may not result in a sustained increase in the per share price of our common stock.

We cannot predict whether the Reverse Split will increase the market price for our common stock on a sustained basis, if at all. The history of similar stock split combinations for companies in like circumstances is varied. There is no assurance that:

•

the market price per share of our common stock after the Reverse Split will rise in proportion to the reduction in the number of shares of our common stock outstanding before the Reverse Split, if it increases at all;

•

~~the Reverse Split will result in a per share price that will attract brokers and investors who do not trade in lower priced stocks; and~~

•

the market price per share will either exceed or remain in excess of the $1.00 minimum bid price as required by Nasdaq, or that we will otherwise meet the requirements of Nasdaq for continued inclusion for trading on Nasdaq.

The market price of our common stock will also be based on our performance and other factors, some of which are unrelated to the number of shares outstanding. If the Reverse Split is effected and the market price of our common stock declines, the percentage decline as an absolute number and as a percentage of our

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overall market capitalization may be greater than would occur in the absence of the Reverse Split. Furthermore, the liquidity of our common stock could be adversely affected by the reduced number of shares that would be outstanding after the Reverse Split.

~~Board Discretion to Implement the Reverse Split~~PROPOSAL NO. 1
AMENDMENT TO AMENDED AND RESTATED ARTICLES OF INCORPORATION TO ELIMINATE CLASSIFIED BOARD STRUCTURE

~~If this proposal is approved by~~Pursuant to the Company’s ~~stockholders,~~Amended and Restated Articles of Incorporation, the Board ~~will have~~of Directors has been divided into three classes, denominated Class I, Class II and Class III, with members of each class holding office for staggered three-year terms or until their respective successors are duly elected and qualified. The Board of Directors currently consists of six members, three of whom are Class I directors whose term expires at this Annual Meeting, one of which is a Class II director whose term expires at the ~~authority, in its sole determination without any further action necessary by~~2025 Annual Meeting, and two of whom are Class III directors whose term expires at the ~~stockholders,~~2026 Annual Meeting.

Our Board of Directors has approved and declared advisable the Charter Amendment, which institutes annual election for each director to ~~effect the Reverse Split during the Authorized Period at~~serve a ~~ratio~~one-year term beginning with this Annual Meeting and makes related changes. The form of Charter Amendment, which is subject to stockholder approval, is set forth in ~~the above range, as determined by the board. The board may, in its sole determination, choose~~Appendix A to ~~not effect the Reverse Split. The board believes that granting~~ this ~~discretionary authority provides the~~Proxy Statement.

Our Board ~~with maximum flexibility to react to prevailing market conditions and future changes to the market price~~of Directors recommends stockholders support Board declassification. Declassification of our ~~common stock,~~Board of Directors would further our goal of ensuring our corporate governance policies, maximize Board accountability to stockholders and ~~therefore better enables it~~would allow stockholders the opportunity each year to ~~act in~~register their views on the ~~best interests of the Company. In exercising its discretion, the board may consider the following factors:~~

•

~~the historical trading price and trading volume~~composition of our ~~common stock;~~Board of Directors.

•

If stockholders approve the ~~then-prevailing trading price and trading volume~~Charter Amendment, four members of our ~~common stock and~~Board of Directors will stand for election for a one-year term at the ~~anticipated impact of the Reverse Split on the trading market for our common stock; and~~

•

~~the prevailing general market and economic conditions.~~

~~At the close of business on December 6, 2023, the Company had 43,779,056 shares of common stock issued and outstanding. Following~~Annual Meeting, such term to commence immediately upon the effectiveness of the ~~Reverse Split, if implemented, at a 1-for-2 ratio,~~Charter Amendment. The incumbent Class II and Class III directors have indicated their support for the ~~Company would have approximately 21,889,528 shares~~declassification of ~~common stock issued and outstanding (without giving effect~~our Board of Directors by agreeing to submit resignations from their current terms that will be effective immediately prior to the treatment of fractional shares or any issuances of common stock after December 6, 2023) following the Reverse Split and at a 1-for-16 ratio, the Company would have approximately 2,736,191 shares of common stock issued and outstanding (without giving effect to the treatment of fractional shares or any issuances of common stock after December 6, 2023) following the Reverse Split. The actual number of shares of common stock outstanding after giving effect to the Reverse Split will depend on the ratio that is ultimately selected by the board, and the number of shares of common stock outstanding at the time the Reverse Split is effected. The Company does not expect the Reverse Split to have any economic effect on stockholders, warrant holders, debt holders or holders of options, except to the extent the Reverse Split results in fractional shares as discussed below.

~~Procedure for Effecting the Reverse Split~~

~~Subject to the stockholder approval, if the board decides to implement the Reverse Split, the board will effect the split at a ratio between 1-for-2 and 1-for-16, to be determined at the discretion~~effectiveness of the ~~board. We~~Charter Amendment.

If stockholders do not approve the Charter Amendment, the election of our one of our three current Class I director nominees to a three-year term will ~~file a Certificate of Amendment to our~~proceed under the Amended and Restated Articles of Incorporation ~~substantially~~as currently in ~~the form attached to this Proxy Statement as~~ ~~Appendix A~~effect (Proposal No. 3), with two of our Class I directors not being re-nominated for re-election, and our Class II and Class III directors will continue to serve the ~~Secretary~~remainder of ~~State of~~their respective terms.

If approved and adopted by stockholders, the ~~State of Nevada to effect the Reverse Split. The Reverse Split would become effective at such time as the Certificate of~~Charter Amendment iswill be filed with the Secretary of State of the State of Nevada ~~or at such later time as is specified therein. No further action on the part~~immediately following certification of the ~~Company’s stockholders would~~voting results with respect to Proposal No. 1 and will be ~~required and all shares of our common stock that were issued and outstanding~~in effect immediately ~~prior thereto would automatically be converted into new shares of our common stock based on~~upon such filing.

Our Board recommends a vote “FOR” the ~~Reverse Split exchange ratio. As soon as practicable after the effective date~~approval of the Reverse Split, stockholders of record on the record date for the implemented Reverse Split would receive a letter from our transfer agent asking them to return the outstanding certificates representing our pre-split shares, which would be cancelled upon receipt by our transfer agent, and new certificates representing the post-split shares of our common stock would be sent to each of our stockholders. We will bear the costs of the issuance of the new stock certificates.Charter Amendment

~~Effects of the Reverse Split~~

If the Reverse Split is approved by the stockholders and implemented by the board, the principal effect will be to proportionately decrease the number of outstanding shares of common stock based on the split ratio. Shares of our common stock are currently registered under Section 12(b) of the Exchange Act and the Company is thus subject to the periodic reporting and other requirements of the Exchange Act. The Reverse Split will not affect the registration of our common stock with the SEC or Nasdaq, where the common stock

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PROPOSAL NO. 2
IF PROPOSAL NO. 1 IS APPROVED, TO ELECT FOUR DIRECTORS

If Proposal No. 1 is ~~traded. Following~~approved, the ~~Reverse Split, our common stock would continue~~Board of Directors will be declassified and stockholders will vote to ~~be listed on Nasdaq, assuming the Company’s compliance with the other continued listing standards of Nasdaq, although the shares will receive a new CUSIP number.~~

Proportionate voting rights and other rights of the holders of shares of our common stock will not be affected by the Reverse Split, other than as a result of the treatment of fractional shares as described below. For example, a holder of 2% of the voting power of the outstanding shareselect four directors to, effective immediately ~~prior to~~upon the effectiveness of the ~~Reverse Split~~Charter Amendment, hold office for a one-year term. In such event, the Board of Directors has recommended Andrew Arno, Lawrence Firestone, Anthony Johnson and Lucille Salhany for election as directors, to serve until the 2025 Annual Meeting and until their successors are duly elected and qualified.

Richard M. Sanders and Dr. Michael Koganov were not renominated to stand for re-election for director. Accordingly, their respective terms as director will ~~generally continue to hold 2%~~expire at this Annual Meeting of Stockholders. Mr. Sanders and Dr. Koganov have been valuable members of the ~~voting power~~Company’s Board of Directors and the ~~outstanding common stock~~Company wishes them the best in their future endeavors. Immediately after the ~~Reverse Split.~~ Annual Meeting of Stockholders, the Board will be reduced from six (6) members to four (4) members.

The number of stockholders of record will not be affected by the Reverse Split, other than as a result of the treatment of fractional shares as described below. If approved and implemented, the Reverse Split may result in some stockholders owning “odd lots” of less than 100 shares. Odd lot shares may be more difficult to sell, and brokerage commissions and other costs of transactions in odd lots are generally somewhat higher than the costs of transactions in “round lots” of even multiples of 100 shares. The Board believes, however, that these potential effects are outweighed by the benefitsnominees for director have each indicated to the Company that they will be available to serve as a director. If a nominee named herein for election as a director should for any reason become unavailable to serve prior to the 2024 Annual Meeting of stockholders, then the Board may, prior to the Annual Meeting, (i) reduce the size of the ~~Reverse Split.~~Board to eliminate the position for which that person was nominated, (ii) nominate a new candidate in place of such person or (iii) leave the position vacant to be filled at a later time.

The ~~table, which does not take into account an increase~~individuals named as proxy voters in the ~~authorized shares~~accompanying proxy, or their substitutes, will vote “FOR” each of the director nominees with respect to upall proxies we receive unless instructions to ~~250,000,000 pursuant~~the contrary are provided. If any nominee for director becomes unavailable for any reason, the votes will be cast for a substitute nominee designated by our Board. We have no reason to ~~Proposal 2 or the board’s authority~~believe that any nominee for director will be unable to ~~effect a reverse stock split without stockholder approval~~serve if ~~the reduction in the number~~elected. We strongly encourage our directors to attend our 2024 Annual Meeting. All of issued and outstanding shares of common stock is coupled with a corresponding decrease in the number of authorized shares of common stock, below illustrates the number of shares of common stock authorized for issuanceour continuing directors attended our 2023 Annual Meeting virtually.

The following the Reverse Split, the approximate number of shares of common stock that would remain outstanding following the Reverse Split, and the number of unreserved shares of common stock available for future issuance following the Reverse Split. Thesets forth certain information, ~~in the following table is based on 43,779,056 shares of common stock issued and outstanding~~ as of ~~December 6, 2023~~April 29, 2024, about the Board’s nominees for election at the Annual Meeting and ~~48,612,817 shares reserved for future issuance as of such date, including 30,134,772 inducement warrants subject to approval in Proposal 3.~~each director whose term will continue after our Annual Meeting.

Proposed Ratio
Number of Shares of
Common Stock
Authorized

Approximate Number of
Shares of Common
Stock Outstanding

Approximate Number of
Unreserved Shares of
Common Stock
Available for Future
Issuance

1-for-2(1) 66,666,667 21,889,528 20,470,730
1-for-16(1) 66,666,667 2,736,191 60,892,174

~~(1)~~Our Board of Directors recommends a vote “FOR” the election of each of its nominees.

~~All share numbers are rounded up to~~

Nominees and Director Qualifications

The following biographies of our nominees contain information regarding the ~~nearest whole share but otherwise do not~~person’s service as a director, business experience, other director positions held currently or at any time during at least the last five years, and information regarding involvement in certain legal or administrative proceedings, if applicable. The biographies reflect the ~~potential effect~~committee memberships the nominees shall hold upon their election.

We believe that each nominee possesses the core competencies that are expected of ~~rounding up for fractional shares~~all directors, namely, independence, integrity, sound business judgment, and a willingness to represent the long-term interests of all stockholders. The experiences, qualifications, attributes, and skills, as shown below, that ~~may result from~~caused the ~~Reverse Split, which is subject~~Corporate Governance and Nominating Committee and the Board to determine that the ~~Board’s discretion to instead pay cash in lieu of any fractional shares.~~

~~As reflected in the table above, the number of authorized shares~~person should serve as a director of our ~~common stock will not be reduced by~~Company are described in each nominee’s biography.

Director Nominees

Name (Age), Principal Occupation, Experience and Other Directorships

Lawrence Firestone (66); Director Since 2023

Mr. Firestone has served as Chief Executive Officer and Chairman of the ~~Reverse Split. Accordingly, the Reverse Split will have the effect~~Board since December 2023. Mr. Firestone brings over 40 years of ~~creating additional unissued~~enterprise, operations, and ~~unreserved shares~~financial management experience in both public and private companies, including tenures as CEO, CFO and COO across multiple industry sectors. Mr. Firestone most recently served as Chief Financial Officer of ~~our common stock. We have no current arrangements or understandings providing~~Oakland Manager, a privately-held purveyor of cannabis with both retail and wholesale market penetration, and as Chairman of FirePower Technology, a privately held manufacturer of ATX power supplies for the ~~issuance~~IT and instrumentation markets. In the public company sector, Mr. Firestone has served as Chief Executive Officer of any of the additional authorized and unreserved shares of our common stock that would be available as a result of the proposed Reverse Split. However, these additional shares may be used by us for various purposes in the future without further stockholder approval (subject to applicable Nasdaq listing rules), including, among other things: (i) raising capital necessary to fund our future operations, (ii) providing equity incentives to our employees, officers, directors and consultants, (iii) entering into collaborations and other strategic relationships and (iv) expanding our business through the acquisition of other businesses or products.

~~Effect of the Reverse Stock Split on the Company’s Equity Incentive Plan, Warrants and Convertible or Exchangeable Securities~~

Based upon the split ratio, proportionate adjustments are generally required to be made to the per share exercise price and the number of shares issuable upon the exercise or conversion of all outstanding options, warrants, convertible or exchangeable securities entitling the holders to purchase, exchange for, or convert into, shares of common stock. This would result in approximately the same aggregate price being required to be paid under such options, warrants, convertible or exchangeable securities upon exercise, and approximatelyEastside Distilling, Inc. (NASDAQ:

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EAST), Chief Executive Officer of Qualstar Corporation (NASDAQ: QBAK), Chief Financial Officer of Advanced Energy Industries (NASDAQ: AEIS), and Chief Financial Officer of Applied Films Corporation (NASDAQ: AFCO). He has served on numerous boards, including those of Eastside Distilling, Qualstar, CVD Equipment Corporation (NASDAQ: CVD), Amtech Systems, Inc. (NASDAQ: ASYS) and HyperSpace Communications, Inc. (NYSE: HYPR). Mr. Firestone received his Bachelor of Science in Business Administration with a concentration in Accounting from Slippery Rock University of Pennsylvania. Mr. Firestone’s prior public company experience led to the ~~same value~~conclusion that he should serve as a director.

Andy Arno (64); Director Since 2023

Mr. Arno previously served, until February 2023, as Vice Chairman of ~~shares~~The Special Equities Group, a division of ~~common stock being delivered upon such exercise, exchange or conversion, immediately following~~Dawson James Securities, Inc., plus other senior roles at investment banking firms. Prior, Mr. Arno served as Vice Chairman and Chief Marketing Officer of Unterberg Capital, LLC, an investment advisory firm that he co-founded, and as Vice Chairman and Head of Equity Capital Markets of Merriman Capital LLC, where he also served on the ~~Reverse Split as~~board of the parent company, Merriman Holdings, Inc. Mr. Arno was responsible for Capital Markets for C.E. Unterberg, Towbin, a Vice President at Lehman Brothers and in the ~~case immediately preceding such split. The number~~Individual Investors Services Division of ~~shares deliverable upon settlement or vesting~~L.F. Rothschild Unterberg, Towbin in portfolio management for high-net-worth individuals. Mr. Arno is currently the Chairman of restricted stock awards will be similarly adjusted, subject to our treatment of fractional shares. The number of shares reserved for issuance pursuant to these securities will be proportionately based upon the ratio determined by the Board ~~subject to our treatment~~ of ~~fractional shares.~~

~~The number~~Oncocyte Corporation and also serves on the boards of ~~shares available under~~directors of Smith Micro Software, Inc., Independa Inc., and Comhear Inc. Mr. Arno previously served as a director of Asterias Biotherapeutics, Inc. from August 2014 until it was acquired by Lineage Cell Therapeutics, Inc. in March 2019. Mr. Arno received a BS degree from George Washington University. He is currently the ~~Company’s Amended and Restated 2021 Omnibus Incentive Plan will not be adjusted in connection with the Reverse Split. Accordingly, following the effective time~~Chair of the ~~Reverse Split, there will be~~Audit Committee. Mr. Arno’s capital markets experience led to the conclusion that he should serve as a director.

Lucille S. Salhany (77); Director since 2022

Ms. Salhany is currently President and CEO of her own consulting company, JHMedia, which she founded in 1997. She was also one of the founding partners of Echo Bridge Entertainment and CEO & President of LifeFX Networks, Inc. Prior to this, she served as Chairperson of the Twentieth Television division of Fox, and was appointed the first woman in history to head a major television network when she accepted the Chairmanship of Fox Broadcasting. After chairing Fox, Salhany accepted the post of Chief Executive Officer and President of United Paramount Network (UPN), launching and growing UPN to become the fifth major broadcast network. She also served on the Board of Directors for Echo Bridge Entertainment, Compaq /Hewlett-Packard, Fox, Inc., Avid Technologies, and American Media, Inc. Lucille was also a trustee of Emerson College and Lasell College, where she received Honorary Doctorates. She is currently a member of the Compensation and Corporate Governance & Nominating Committees of the Board. Ms. Salhany’s well-established track record of success in growing businesses and strong background in and knowledge of the media industry led to the conclusion that she should serve as a director.

Anthony Johnson (48); Director since 2021;

Mr. Johnson is co-founder, President, and CEO of Kodikaz Therapeutic Solutions, a next-generation non-viral gene therapy company. He is also a founding partner of Buffalo Biosciences in 2006 a life science strategic business management firm that supports the evaluation and commercialization of bioscience technologies from concept to market. Previously he was President and CEO of Empire Genomics, an ~~increase~~oncology molecular diagnostic testing company, from 2006 until 2019. He also served as the business leader of the stem cell and regenerative medicine franchise for Thermo Fisher (Invitrogen Corporation). Anthony has leveraged his business experience and numerous board positions to mentor technology startups and entrepreneurs, spur state and local job creation, and introduce STEM curriculum into early childhood education. Mr. Johnson is a founding board member of the Communities of Giving Legacy Initiative, which works to create positive change in the ~~number~~lives of ~~available shares~~low-income youth of ~~our common stock available~~color. Additionally, he serves as Michigan Street African-American Heritage Corridor Commissioner and was an Opportunities Council member for ~~future awards. Additional shares~~University of ~~common stock, if issued in connection~~Buffalo. He holds an MBA from Manchester Business School, Manchester, UK, with an ~~equity award, would have~~emphasis in international strategy, and a ~~dilutive effect upon~~BA in biology from Fisk University, Nashville, TN. He is the ~~percentage of equity~~Chair of the ~~Company owned by our present stockholders.~~

~~Accounting Matters~~

~~The amendment~~Audit Committee and is a member of the Corporate Governance & Nominating Committee. Mr. Johnson’s experience commercializing bioscience technologies and life sciences experience led to the Company’s Articles of Incorporation will not affect the par value of our common stock per share, which will remain $0.00001 par value per share. As a result, the stated capital attributable to common stock and the additional paid-in capital account on our balance sheet will not change due to the Reverse Split.

~~Effective Date~~

The Reverse Split would become effective upon the filing of a Certificate of Amendment to our Articles of Incorporation with the office of the Secretary of State of the State of Nevada or at such later date as is specified in such filing. On the effective date, shares of common stock issued and outstanding, in each case, immediately prior thereto, will be combined and converted, automatically and without any action on the part of the stockholders, into new shares of common stock in accordance with the ratio determined by the Board within the limits set forth in this proposal.

~~No Going Private Transaction~~

Notwithstanding the decrease in the number of outstanding shares of common stock following the implementation of the Reverse Split, the board does not intend for this transaction to be the first step in a “going private transaction” within the meaning of Rule 13e-3 of the Exchange Act and the implementation of the proposed Reverse Split will not cause the Company to go private.

~~Treatment of Fractional Shares~~

~~No fractional shares would be issued if,~~conclusion that he should serve as a result the Reverse Split, a registered stockholder would otherwise become entitled to a fractional share. Rather, either (i) fractional shares that would be created as a result of the Reverse Split will be rounded upward to the nearest whole share, or (ii) stockholders will receive cash equal to the market value of the fractional share, determined by multiplying such fraction by the closing sales price of the common stock as reported on the Nasdaq on the last trading day before the effective date of the Reverse Split (as adjusted to give effect to the Reverse Split), with such determination regarding the treatment of fractional shares to be made by the Board in its sole discretion prior to effecting the Reverse Split. The ownership of a fractional share will not give a stockholder any voting, dividend or other right except, to the extent the Board decides to pay cash in lieu of fractional shares, the right to receive the cash payment therefor. If a stockholder is entitled to a cash payment in lieu of any fractional share, a check will be mailed to the stockholder’s registered address as soon as practicable after the effective date of the Reverse Split. By signing and cashing the check, stockholders will warrant that they owned the shares of common stock for which they received such cash payment. To the extent the Board decides to round up fractional shares, share interests issued due to rounding will be given solely to save the expense and inconvenience of issuing fractional shares of common stock and will not represent separately bargained for consideration.

~~Book-Entry Shares~~

If the Reverse Split is effected, stockholders who hold uncertificated shares (i.e., shares held in book-entry form and not represented by a physical share certificate), either as direct or beneficial owners, will have theirdirector.

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~~holdings electronically adjusted~~Commitment to Corporate Governance

Board of Directors

Our Board of Directors represents the best interests of our stockholders by overseeing the business and affairs of the Company. Members of the Board participate in quarterly Board and Committee meetings, engage with senior management of the Company, review, provide input, approve the Company’s ~~transfer agent (and, for beneficial owners, by their brokers or banks that hold in “street name” for their benefit, as the case may be) to give effect to the Reverse Split.~~strategic plan and principal issues, and discuss feedback from stockholders and other stakeholders.

~~Stockholders who hold uncertificated shares as direct owners will be sent a statement of holding from~~Under the Company’s ~~transfer agent~~current Amended and Restated Articles of Incorporation, directors hold office for a term ending on the date of the third annual stockholders’ meeting following the Annual Meeting at which such director’s class was most recently elected until the earlier of their death, resignation, removal or until their successors have been duly elected and qualified. If the Charter Amendment proposal (Proposal 1) is approved, Directors will hold office for a term ending on the next annual stockholder meeting. Our Bylaws provide that ~~indicates~~ the number of ~~shares owned in book-entry form.~~

~~Certificated Shares~~

If the Reverse Split is effected, stockholders holding certificated shares (i.e., shares represented by one or more physical share certificates) will receive a transmittal letter from the Company’s transfer agent promptly after the effectiveness of the Reverse Split. The transmittal letter will be accompanied by instructions specifying how stockholders holding certificated shares can exchange certificates representing the pre-split shares for a statement of holding.

~~Beginning after the effectiveness of the Reverse Split, each certificate representing shares~~members of our ~~pre-split common stock will~~Board of Directors may be ~~deemed for all corporate purposes~~changed from time to ~~evidence ownership~~time by resolutions adopted by the Board of ~~post-split common stock.~~

~~STOCKHOLDERS SHOULD NOT DESTROY ANY PRE-SPLIT STOCK CERTIFICATE AND SHOULD NOT SUBMIT ANY CERTIFICATES UNTIL THEY ARE REQUESTED TO DO SO.~~

~~Possible Effects~~Directors. Our Board of ~~Additional Issuances~~Directors currently consists of ~~Common Stock and History of Prior Reverse Splits~~

six (6) members with no vacancies. Following the ~~effective time of the Reverse Split, there will be an increase in the number of authorized but unissued shares of our common stock. Under the Nevada Revised Statutes (the “NRS”),~~meeting, the Board ~~can issue additional shares~~will consist of common stock without further vote of our stockholders except as may be required in particular cases by our Articles of Incorporation, the NRS or other applicable law, regulatory agencies or Nasdaq Listing Rules. Stockholders do not have preemptive rights to subscribe to additional securities that we may issue, which means that current stockholders do not have a prior right thereunder to purchase any new issue of common stock, or securities that are convertible into common stock, in order to maintain their proportionate ownership interests in the Company.

Additional shares of common stock, if issued, would have a dilutive effect upon the percentage of equity of the Company owned by our present stockholders. The issuance of such additional shares of common stock might be disadvantageous to current stockholders in that any additional issuances would potentially reduce per share dividends, if any. Stockholders should consider, however, that the possible impact upon dividends is likely to be minimal in view of the fact that the Company does not intend to pay any cash dividends on its common stock in the foreseeable future. In addition, the issuance of such additional shares of common stock, by reducing the percentage of equity of the Company owned by present stockholders, would reduce such present stockholders’ ability to influencefour (4) members with no vacancies, assuming the election of the director nominees.

Independent Directors

Our Board of Directors has determined that Anthony Johnson, Lucille S. Salhany, and Andrew Arno are “independent” as defined by applicable Nasdaq Stock Market listing standards. Each director serving on the Audit Committee and the Compensation Committee of our Board also meets the more stringent independence requirements established by SEC and Nasdaq rules applicable to audit and compensation committees. Our Board has determined that no director or nominee has a relationship that would interfere with the exercise of independent judgment in carrying out their responsibilities as a director. There are no family relationships among our directors, nominees, or ~~any~~executive officers. The Board annually reviews all business and other ~~action taken~~relationships of directors and determines whether directors meet these categorical independence tests.

Board Leadership Structure and the Role of the Board in Oversight of Risk Management

Our Board of Directors has not adopted a policy requiring that the roles of Chief Executive Officer and chairperson of the Board be separate. Our Board reserves the right to assign the responsibilities of the Chief Executive Officer and chair position as determined by our Board to be in the ~~holders~~best interest of ~~common stock.~~

our Company. In the ~~future~~circumstance where the responsibilities of the Chief Executive Officer and chair are vested in the same individual or in other circumstances when deemed appropriate, the Board will designate a Lead Independent Director from among the independent directors to preside at the meetings of non-employee director executive sessions.

Currently, Lawrence D. Firestone serves as Board Chair and Chief Executive Officer, and Andrew Arno serves as the Lead Independent Director. Our Board reviews our leadership structure annually and retains the authority to modify this structure to best address our Company’s unique circumstances as and when appropriate.

Our Board is actively involved in oversight of risks that could ~~subject~~affect the Company. Our Board has assigned responsibility for addressing certain risks, and the steps management has taken to ~~its fiduciary duties~~monitor, control and ~~applicable law, use the increased number of authorized but unissued shares of common stock~~report such risk, to ~~frustrate persons seeking~~our Audit Committee, including risks relating to ~~take over or otherwise gain control~~execution of our growth strategy, with appropriate reporting to the full Board. Our Board relies on our Compensation Committee to address significant risk exposures facing our Company with respect to compensation. Our Board receives reports by each committee chair regarding the applicable committee’s considerations and actions, as well as through regular reports directly from officers responsible for ~~example, privately placing shares with purchasers who might side~~oversight of particular risks within the Company.

Stockholder Communications with the Board ~~in opposing a hostile takeover bid. Shares~~

Stockholders wishing to communicate with the Board of ~~common stock could also be issued to a holder that would thereafter have sufficient voting power to assure that any proposal to amend~~Directors or ~~repeal the Company’s bylaws or Articles of Incorporation would not receive the requisite vote. Such uses of the common stock could render more difficult, or discourage,~~with an ~~attempt to acquire control of~~individual Board member concerning the Company ~~if such transactions were opposed~~may do so by the Board. A result of the anti-takeover effect of the increase in the number of authorized shares of common stock could be that stockholders would be denied the opportunity to obtain any advantages of a hostile takeover, including, but not limited to, receiving a premiumwriting to the ~~then current market price~~Board or to the particular Board member care of ~~our common stock, if~~ the same was so offered by a party attempting a hostile takeover of our Company. The Company is not aware of any party’s interest in or efforts to engage in a hostile takeover attempt as of the date of this Proxy Statement.

The Company previously effected a 1-for-15 reverse stock split of the Company’s issued and outstanding shares of common stock on July 5, 2023. The Company effected this reverse stock split for the purpose of complying with Nasdaq Listing Rule 5550(a)(2).

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Corporate Secretary, 22nd Century Group, Inc. The envelope or subject line should indicate that it contains a stockholder communication.

~~Certain Material U.S. Federal Income Tax Consequences~~Meetings of Board of Directors

Our Board held 40 meetings throughout 2023. All directors attended at least 75% of meetings of the Board and Board committees on which they served in 2023.

We do not have a ~~Reverse Stock Split~~formal policy requiring directors to attend Annual Meetings of stockholders. However, all of our continuing directors who were members of the Board at the time of our 2023 Annual Meeting attended the meeting virtually, and we anticipate that all continuing directors will attend the 2024 Annual Meeting.

Executive Sessions of Independent Directors

The ~~following discussion summarizes certain material U.S. federal income tax consequences relating~~independent directors hold regularly scheduled executive sessions of the Board and its committees no management directors or employees present. The independent directors met in executive session at most of the regularly scheduled Board and committee meetings held in 2023.

Corporate Governance Guidelines

Our Board has adopted a set of Corporate Governance Guidelines, which describe the Board’s responsibility for oversight of the business and affairs of the Company as well as guidelines for determining director independence and consideration of potential nominees to the ~~participation~~Board. The Board, directly and through its Corporate Governance and Nominating Committee, regularly reviews developments in corporate governance and best practices and annually reviews its Corporate Governance Guidelines, committee charters, and other key governance documents, policies, and practices. Our Corporate Governance Guidelines provide:

•

Limits on Board Service. We do not allow “over-boarding,” or a ~~reverse stock split~~director serving on an excessive number of public company boards. Excessive board commitments can lead to a director being unable to appropriately fulfill his or her duties to the Company and its stockholders. Our Corporate Governance Guidelines have long limited our directors to no more than two (2) other public company boards.

•

Board Self-Assessment and Evaluation. We conduct an annual self-evaluation and assessment of our individual Board performance to help ensure that the Board and its committees function effectively and in the best interest of our stockholders. This process promotes governance in accordance with current best practices and helps set expectations about the relationship and interaction of and between the Board and management.

Standing Committees

Our Board of Directors currently has three (3) standing committees: (i) an Audit Committee, (ii) a Compensation Committee, and (iii) a Corporate Governance and Nominating Committee. Members of these committees are elected annually by ~~a U.S. stockholder who holds~~ the ~~shares as a capital asset. This discussion is based~~Board. The charters of each committee are each available on the ~~provisions~~investor relations section of our website at www.xxiicentury.com.

The Audit Committee oversees the Company’s financial reporting process and system of internal accounting controls, as well as appointment and oversight of the ~~U.S. Internal Revenue Code of 1986, as amended (the “Code”), final, temporary~~independent public accountants engaged to audit the Company’s financial statements. The Audit Committee also assists the Board in monitoring compliance with legal and ~~proposed U.S. Treasury regulations promulgated thereunder~~regulatory requirements and ~~current administrative rulings and judicial decisions, all as in effect as of~~oversees the date hereof. All of these authorities may be subject to differing interpretations or repealed, revoked or modified, possibly with retroactive effect, which could materially alter the tax consequences set forth herein.

For purposes of this summary, a “U.S. stockholder” refers to a beneficial owner of common stock who is any of the following for U.S. federal income tax purposes: (i) a citizen or resident of the United States, (ii) a corporation created or organized in or under the laws of the United States, any state thereof, or the District of Columbia, (iii) an estate the income of which is subject to U.S. federal income taxation regardless of its source, or (iv) a trust if (1) its administration is subject to the primary supervision of a court within the United States and one or more U.S. persons have the authority to control all of its substantial decisions, or (2) it has a valid election in effect under applicable U.S. Treasury regulations to be treated as a U.S. person. A non-U.S. holder of common stock is a stockholder who is not a U.S. stockholder.

This summary does not represent a detailed description of the U.S. federal income tax consequences to a stockholder in light of his, her or its particular circumstances. In addition, it does not purport to be complete and does not address all aspects of federal income taxation that may be relevant to stockholders in light of their particular circumstances or to any stockholder who may be subject to special tax rules, including, without limitation: (1) stockholders subject to the alternative minimum tax; (2) banks, insurance companies, or other financial institutions; (3) tax-exempt organizations; (4) dealers in securities or commodities; (5) regulated investment companies or real estate investment trusts; (6) traders in securities who elect to use a mark-to-market method of accounting for their securities holdings; (7) U.S. stockholders whose “functional currency” is not the U.S. dollar; (8) persons holding common stock as a position in a hedging transaction, “straddle,” “conversion transaction” or other risk reduction transaction; (9) persons who acquire shares of common stock in connection with employment or other performance of services; (10) dealers and other stockholders who do not own their shares of common stock as capital assets; (11) U.S. expatriates, (12) foreign persons; (13) resident alien individuals; or (14) stockholders who directly or indirectly hold their stock in an entity that is treated as a partnership for U.S. federal tax purposes. Moreover, this description does not address the U.S. federal estate and gift tax, alternative minimum tax, or other tax consequences of the Reverse Split.

There can be no assurance that the Internal Revenue Service (the “IRS”) will not take a contrary position to the tax consequences described herein or that such position will be sustained by a court. In addition, U.S. tax laws are subject to change, possibly with retroactive effect, which may result in U.S. federal income tax considerations different from those summarized below. No opinion of counsel or ruling from the IRS has been obtainedCompany’s policies with respect to ~~the U.S. federal income tax consequences~~risk assessment and management, including but not limited to cybersecurity risks.

The Audit Committee is comprised solely of ~~the Reverse Split.~~

~~This discussion is for general information only and is not tax advice. All stockholders should consult their own tax advisors~~non-employee directors who satisfy current Nasdaq standards with respect to independence, financial expertise and experience. During 2023, the ~~U.S. federal, state, local~~Audit Committee was comprised of Mr. Johnson, Mr. Sanders, Dr. Koganov and ~~non-U.S. tax consequences~~Nora B. Sullivan. On August 24, 2023, Mr. Arno was appointed to the committee. Our Board of Directors has determined that Mr. Arno meets the SEC’s definition of “audit committee financial expert,” and that all members of the ~~Reverse Split.~~

~~Tax Consequences to~~Audit Committee meet the ~~Company~~ ~~— We believe that the Reverse Split will constitute a reorganization under Section 368(a)(1)(E)~~financial literacy requirements of the Code. Accordingly, we should not recognize taxable income, gain or loss in connection with the Reverse Split. In addition, we do not expect the Reverse Split to affect our ability to utilize our net operating loss carryforwards.

~~Tax Consequences to Stockholders~~ ~~— Stockholders should not recognize any gain or loss for U.S. federal income tax purposes as a result~~Nasdaq Stock Market. No members of the ~~Reverse Split, except to~~Audit Committee serve on the ~~extent~~audit committees of any cash received in lieu of a fractional share of common stock (which fractional share will be treated as received and then exchanged for cash), to the extent the Board decides to pay cash in lieu of any fractional shares. Each stockholder’s aggregate tax basis in the common stock received in the Reverse Split, including any fractional share treated as received and then exchanged for cash, should equal the stockholder’s aggregate tax basis in the common stock exchanged in the Reverse Split. In addition, each stockholder’s holding period for the common stock it receives in the Reverse Split should include the stockholder’s holding period for the common stock exchanged in the Reverse Split.more than three public companies. The Audit Committee held 4 meetings during

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2023. To ensure independence, the Audit Committee also meets separately with our independent public accountants apart from meetings with members of management. At the time of the 2024 Annual Meeting, the Audit Committee will consist of Mr. Johnson, Ms. Salhany and Mr. Arno as Chair.

The Compensation Committee is comprised solely of directors who meet the current Nasdaq requirements for independence. During 2023, the Compensation Committee was comprised of Ms. Salhany, Mr. Sanders, Ms. Sullivan and Dr. Koganov. On August 24, 2023, Mr. Arno was appointed to the committee. The Compensation Committee establishes and regularly reviews our compensation and benefits philosophy and program in a manner consistent with corporate financial goals and objectives. The Compensation Committee also approves compensation arrangements for senior management, including annual incentive and long-term compensation; administers grants under our equity incentive plans; annually evaluates the performance of our Chief Executive Officer; and reviews leadership development and succession planning. The Compensation Committee held 8 meetings in 2023. At the time of the 2024 Annual Meeting, the Compensation Committee will consist of Mr. Arno, Mr. Johnson and Ms. Salhany as Chair.

The Corporate Governance and Nominating Committee is comprised solely of independent directors and during 2023 was comprised of Mr. Johnson, Ms. Salhany and Ms. Sullivan. The Corporate Governance and Nominating Committee develops and recommends to the Board corporate governance guidelines applicable to the Company; identifies, evaluates and recommends candidates for election to the Board; leads the Board in its annual review of the Board’s performance; and recommends Board members to serve on each committee of the Board. The Corporate Governance and Nominating Committee held 7 meetings in 2023. At the time of the 2024 Annual Meeting, the Corporate Governance and Nominating Committee will consist of Mr. Arno, Ms. Salhany Mr. Johnson as Chair.

The guidelines and procedures for identifying and evaluating nominees for election to the Board are set forth in the charter of the Corporate Governance and Nominating Committee. In general, apersons considered for nomination to the Board must have demonstrated outstanding achievement, integrity and judgment and such other skills and experience as will enhance the Board’s ability to serve the long−term interests of the Company and its stockholders. Candidates must also be willing and able to devote the necessary time for Board service. The Corporate Governance and Nominating Committee also considers diversity in terms of gender, ethnicity, age, and other attributes that could contribute to Board effectiveness, and assesses diversity in the course of the Committee’s annual evaluation of Board structure and composition. The Corporate Governance and Nominating Committee considers potential candidates recommended by current directors, company officers, employees and others, and will consider candidates recommended by stockholders for consideration as director nominees. Nominations of persons for election to the Board at the Annual Meeting may be made by any stockholder entitled to vote for the election of directors at the meeting who ~~receives cash~~complies with the notice procedures set forth in ~~lieu of a fractional share of common stock~~our Bylaws. Such nominations by any stockholder shall be made pursuant to ~~the Reverse Split should be treated for U.S. federal income tax purposes as having received a fractional share pursuant~~timely notice in writing to the ~~Reverse Split and then as having received cash in exchange for the fractional share and should generally recognize capital gain or loss equal~~Secretary. To be timely, a stockholder’s notice shall be delivered to the ~~difference between~~Secretary at our principal executive offices not later than the ~~amount~~close of ~~cash received and~~business on the ~~stockholder’s tax basis allocable~~ninetieth (90th) day nor earlier than the close of business on the one hundred twentieth (120th) day prior to the ~~fractional share. Any capital gain or loss will generally be long term capital gain or loss if~~first anniversary of the ~~stockholder’s holding period~~preceding year’s Annual Meeting; provided, however, that in the ~~fractional share is greater than one year as of~~event that the ~~effective~~ date of the ~~Reverse Split. Special rules may apply~~Annual Meeting is more than thirty (30) days before or more than seventy (70) days after such anniversary date, notice by the stockholder must be so delivered not earlier than the close of business on the one hundred twentieth (120th) day prior to ~~cause all or a portion~~such Annual Meeting and not later than the close of business on the later of the ~~cash received in lieu of a fractional share~~ninetieth (90th) day prior to ~~be treated as dividend income with respect to certain stockholders who own more than a minimal amount of common stock (generally more than 1%)~~such Annual Meeting or ~~who exercise some control over~~ the ~~affairs~~tenth (10th) day following the day on which public announcement of the ~~Company. Stockholders should consult their own tax advisors regarding the tax effects to them of receiving cash in lieu of fractional shares based on their particular circumstances.~~

THE PRECEDING DISCUSSION IS INTENDED ONLY AS A SUMMARY OF CERTAIN FEDERAL INCOME TAX CONSEQUENCES OF THE REVERSE SPLIT AND DOES NOT PURPORT TO BE A COMPLETE ANALYSIS OR DISCUSSION OF ALL POTENTIAL TAX EFFECTS RELEVANT THERETO. YOU SHOULD CONSULT YOUR OWN TAX ADVISORS AS TO THE PARTICULAR FEDERAL, STATE, LOCAL, FOREIGN AND OTHER TAX CONSEQUENCES OF THE REVERSE SPLIT IN LIGHT OF YOUR SPECIFIC CIRCUMSTANCES.

~~No Right of Dissent or Appraisal~~

~~Under NRS 92A.300 to 92A.500, inclusive, under certain circumstances, stockholders of a Nevada corporation may be entitled to dissent and demand payment of the fair value~~date of such ~~stockholder’s shares in the event~~meeting is first made.

Code of certain corporate actions, including reverse stock splits of a class or series held without correspondingly decreasing the number of authorized shares of the same class or series if money will be paid or scrip will be issued to stockholders who in the aggregate hold one percent or more of the outstanding shares of the affected class or series,Business Conduct and ~~would otherwise be entitled to receive a fraction of a share in the exchange of their outstanding shares.~~Corporate Ethics

However, there is no such right of dissent for holders of a class or series of stock that is a “covered security” under Section 18(b)(1)(A) or (B) of the Securities Act. The Company’s common stock is listed on the Nasdaq Capital Market, a national securities exchange, making it a “covered security” within the meaning of Section 18(b)(1)(A) of the Securities Act. Therefore, the holders of common stock will not have the right under the NRS to dissent from, or demand payment for their shares in connection with, Proposal 1, and we will not independently provide our stockholders with such a right.

~~Interests of Directors and Executive Officers~~

~~None.~~

Our Board of Directors ~~recommends~~has long maintained a Code of Ethics that ~~the stockholders vote “FOR” Proposal 1~~applies to
~~approve an amendment to the Articles~~ all our directors, officers, and employees. A copy of ~~Incorporation to effect the Reverse Split.~~our Code of Ethics is available on our website at http://www.xxiicentury.com.

Insider Trading Policy

Our directors, executive officers, and employees are required to comply with the 22nd Century Group, Inc. Insider Trading Policy and may not engage in any transaction (such as short-selling) to hedge against the potential decline in value of any of our securities. Our Insider Trading policy also clearly sets forth the prohibition on trading based on material non-public information.

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PROPOSAL TWO: APPROVAL OF AN INCREASE IN THE NUMBER OF SHARES OF AUTHORIZED COMMON STOCK FROM SIXTY-SIX MILLION SIX HUNDRED SIXTY-SIX THOUSAND SIXTY HUNDRED SIXTY-SEVEN (66,666,667) TO TWO HUNDRED FIFTY MILLION (250,000,000)Board Diversity Matrix

2023
(as of April 25, 2023)

Total Number of Directors

Female

Male

Part I: Gender Identity

Directors

Part II: Demographic Background

African American or Black

White

LGBTQ

None

2024
(as of April 29, 2024)

Total Number of Directors

Female

Male

Part I: Gender Identity

Directors

Part II: Demographic Background

African American or Black

White

LGBTQ

None

Compensation of Directors

~~General~~Elements of 2023 Non-Employee Director Compensation

~~Under~~Non-employee directors are compensated for their service on our ~~Restated Articles of Incorporation (as amended, “Articles of Incorporation”), the total number of shares of all classes of capital stock that we~~Board as shown below. Directors who are authorized to issue is seventy-six million, six hundred sixty-six thousand six hundred sixty-seven (76,666,667), consisting of (i) sixty-six million, six hundred sixty-six thousand six hundred sixty-seven (66,666,667) designated as common stock, $0.00001 par value per share, and (ii) ten million (10,000,000) designated as preferred stock, $0.00001 par value per share. Our Board of Directors has determined that it is advisable to increase (i) the authorized number of authorized shares from seventy-six million, six hundred sixty-six thousand six hundred sixty-seven (76,666,667) to two hundred and sixty million (260,000,000) and (2) the authorized number of shares of common stock from sixty-six million, six hundred sixty-six thousand sixty hundred sixty-seven (66,666,667) to two hundred fifty million (250,000,000) and recommends that our stockholders approve an amendment to our Articles of Incorporation to effect the proposed increases. The authorized number of shares of preferred stock will not change. The amendment to the Articles of Incorporation that you are being asked to approve pursuant to this Proposal 2 will be substantially in the form of ~~Appendix B~~ ~~attached to this Proxy Statement.~~

~~Purpose of the Increase in Authorized Shares~~

As of December 6, 2023, we had sixty-six million, six hundred sixty-six thousand six hundred sixty-seven (66,666,667) shares of common stock authorized, of which 43,779,056 shares were issued and outstanding. Of the remaining 22,887,611 authorized shares, 47,632,580 shares are reserved for issuance upon the exercise of issued and outstanding warrants, 227,852 shares are reserved for issuance upon the exercise of issued and outstanding equity option awards, 296,909 shares are reserved for unvested restricted stock units and 455,476 shares are reserved for future issuance under our stock incentive plan. The Inducement Warrants (defined below) are not exercisable unless and until our stockholders approve Proposal 3. Accordingly, based on the foregoing, we do not have enough shares of common stock available for future issuance.

Our Board believes it is in the best interest of our Company to increase the number of authorized shares of our common stock to give us greater flexibility in considering and planning for future potential business needs, including to raise additional capital in connection with future equity financings, future opportunities for expanding the business through investments or acquisitions, management incentive and employee benefit plans and for other general corporate purposes.

Furthermore, as a material condition to the warrant inducement offering described in Proposal 3, we agreed to submit and recommend this proposal to our stockholders. If we do not obtain stockholder approval for this Proposal 2 (unless Proposal 1 is approved and the Reverse Split is implemented) and Proposal 3 at the Special Meeting, or any adjournment of the Special Meeting, we have agreed to call a meeting of stockholders every 90 days thereafter to seek stockholder approval until the necessary stockholder approval is obtained, which will result in additional management resources and expenses to us.

~~Rights of Additional Authorized Shares~~

~~The proposed amendment to our Articles of Incorporation would not have any effect on the par value per share~~compensation of our ~~common stock. Our common stock~~non-employee directors and considers market practices.

During 2022 and 2023, the Compensation Committee received advice and recommendations from Pay Governance LLC regarding compensation benchmarking as compared to a peer group of companies, including compensation of non-employee directors (see below, “Compensation Discussion and Analysis — Benchmarking Against Peer Companies”). Upon review, the Compensation Committee recommended, and the Board approved, maintaining the 2022 level of non-employee director compensation for 2023 which is a single class, with equal voting, distribution, liquidation and other rights. The additional common stock to be authorized by the proposed amendment would have rights identical to our currently outstanding common stock. Should our Board issue additional shares of common stock, existing stockholders would not have any preferential rights to purchase any newly authorized shares of common stock solely by virtue of their ownership of shares of our common stock, andset forth below.

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		2023 Director Compensation (non-employee)1
		Annual cash retainer:				$75,000
		Additional Board Fees:
		Chair of the Board				$50,000
		Chair of a Board Committee				$20,000
		Member of a Board Committee				$10,000
		Annual RSU award value:				$135,000

~~their percentage ownership of our then outstanding common stock could be reduced. The issuance of additional shares of common stock would have~~Given the ~~effect of diluting existing stockholder earnings per share, book value per share and voting power.~~

~~Potential Adverse Effects~~

We have not proposed the increase in the number of authorized shares of common stock with the purpose or intention of using the additional authorized shares for anti-takeover purposes, such as to oppose a hostile takeover attempt or to delay or prevent a change in control of the Company that our Board does not support, but we could use the additional shares for such purpose. The proposed amendment, if effected, will increase the number of authorized but unissued shares of our common stock, and, subject to compliance with law and the listing rules of the Nasdaq Stock Market, our Board could issue, without further stockholder approval, the additional shares available as a result of such increase in one or more transactions that could make it more difficult for a party to effect a takeover or change in control of the Company that our Board does not support.

~~Risks of Not Approving This Proposal~~

If the stockholders do not approve this proposal, our ability to pursue opportunities in which shares of our common stock could be issued that our Board may determine would otherwise be in the best interestrecent performance of the Company and ~~our stockholders, including financing and strategic transaction opportunities and employee recruitment and retention purposes, as described above under~~ the ~~header, “Purpose~~resulting cash constraints, the Board approved a significant reduction in the cash compensation for non-employee directors in 2024 along with the removal of the ~~Increase in Authorized Shares” would be negatively impacted.~~equity component, as set forth below:

		2024 Director Compensation (non-employee)2
		Annual cash retainer:				$20,000
		Chair of the Board or Lead Independent Director				$20,000
		Chair of Audit Committee				$10,000
		Chair of Compensation or Corporate Governance & Nominating Committee				$5,000
		Member of a Board Committee				$5,000
		Annual RSU award value:				$0

~~Interests of Directors and Executive Officers~~

~~None.~~

~~Our~~1

The Directors voted to forfeit payment of their cash fees for the fourth quarter of 2023, thus the cash actually paid is lower than reflected in the table.

The Board ~~of Directors recommends that~~voted to forgo any director compensation until after the ~~stockholders vote “FOR” Proposal 2 to~~
~~increase~~2024 Annual Stockholder Meeting, thus the ~~number of authorized shares of our common stock.~~director compensation paid in 2024 will be lower than reflected in the table.

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NON-EMPLOYEE DIRECTOR COMPENSATION FOR 2023

Name	Fees earned or paid in cash(1)			Option Awards			Restricted Stock Unit Awards(2)			All Other Compensation			Total
Clifford B. Fleet(6)		$	37,500		$	—		$	—		$	—		$	37,500
Anthony Johnson		$	81,250		$	—		$	106,406		$	—		$	187,656
Michael Koganov		$	81,250		$	—		$	106,406		$	—		$	187,656
Roger D. O’Brien(6)		$	47,500		$	—		$	—		$	—		$	47,500
Richard M. Sanders		$	83,750		$	—		$	106,406		$	—		$	190,156
Lucille S. Salhany		$	68,750		$	—		$	106,406		$	—		$	175,156
Nora B. Sullivan(3)(6)		$	388,750		$	—		$	106,406		$	—		$	495,156
James Mish(4)(6)		$	7,083		$	—		$	—		$	—		$	7,083
Andrew Arno(5)		$	19,103		$	—		$	—		$	—		$	19,103

(1)

On February 9, 2024, the Board of Directors voted to waive any cash compensation for non-employee directors for the fourth quarter of 2023 and the first quarter of 2024. All amounts reflected as fees earned or paid in cash exclude the cash portion waived in the aggregate amount of $193,750.

(2)

The fair value of each restricted stock unit is based on the stock price of the Company’s common stock on the grant date of the award.

(3)

Ms. Sullivan assumed a leadership role in the second half of 2023 overseeing all non-tobacco functions, including human resources, research and development, finance, legal and investor relations, receiving additional fees of $260,000.

(4)

Mr. Mish resigned from employment as Chief Executive Officer on July 21, 2023 and therefore received pro rata compensation for service as a director subsequent to this date during the third quarter of 2023.

(5)

Mr. Arno was appointed as a director on July 19, 2023 and received pro rata compensation for service during 2023.

(6)

Former director.

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PROPOSAL ~~THREE:~~ NO. 3
IF PROPOSAL NO. 1 IS NOT APPROVED, ELECT TWO CLASS I DIRECTORS

If Proposal No. 1 is not approved, the Board of Directors will remain classified and stockholders will vote to elect one (1) Class I director. The Board of Directors is currently divided into three classes, with each class serving a three-year term or until the earlier of: (i) expiration of the term of their class of directors; or (ii) until their successors are elected and take office as provided below. The term of the current Class I directors will expire at the Annual Meeting.

In the event Proposal No. 1 is not approved, the Board of Directors has recommended Andrew Arno for election as Class I director, to serve until the 2027 Annual Meeting and until his successor is duly elected and qualified.

Lawrence Firestone will continue as a Class II director, and Anthony Johnson and Lucille Salhany will continue as Class III directors.

The nominees for director have each indicated to the Company that they will be available to serve as a director. If a nominee named herein for election as a director should for any reason become unavailable to serve prior to the 2024 Annual Meeting, then the Board may, prior to the Annual Meeting, (i) reduce the size of the Board to eliminate the position for which that person was nominated, (ii) nominate a new candidate in place of such person or (iii) leave the position vacant to be filled at a later time.

The individuals named as proxy voters in the accompanying proxy, or their substitutes, will vote “FOR” each of the director nominees with respect to all proxies we receive unless instructions to the contrary are provided. If any nominee for director becomes unavailable for any reason, the votes will be cast for a substitute nominee designated by our Board. We have no reason to believe that any nominee for director will be unable to serve if elected.

Information regarding the director nominees is set forth above under the heading “Board of Directors.”

Our Board of Directors recommends a vote “FOR” the election of the director nominee as a Class I Director.

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PROPOSAL NO. 4
ADVISORY VOTE ON EXECUTIVE COMPENSATION

We design our executive officer compensation programs with the intent to attract, motivate, and retain industry-leading executives capable of achieving our key strategic goals. Our compensation programs are designed to be competitive with comparable employers and to align the interests of management with those of our stockholders by creating incentives for the achievement of specific corporate objectives and long-term value creation. We encourage you to closely review our “Compensation Discussion and Analysis” and “Executive Compensation” sections for more information.

In accordance with SEC rules, you are being asked to approve an advisory resolution on the compensation of our named executive officers. This proposal, commonly known as a “say on pay” proposal, gives you the opportunity to endorse or not endorse our fiscal year 2023 compensation program and policies for our named executive officers. Although this vote is advisory and not binding on the Company, our Board and Compensation Committee will review and consider voting results in making future decisions about executive compensation programs.

RESOLVED:

That the stockholders of 22nd Century Group, Inc. approve, on an advisory basis, the compensation paid to the Company’s named executive officers as described in this proxy statement under the headings “Compensation Discussion and Analysis” and “Executive Compensation.”

Our Board recommends a vote “FOR” approval, on an advisory basis, the 2023 compensation of the Company’s named executive officers as described in this proxy statement under the headings “Compensation Discussion and Analysis” and “Executive Compensation.”

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COMPENSATION DISCUSSION AND ANALYSIS

This section contains a discussion of the material elements of compensation awarded to, earned by, or paid to our principal executive officer, our principal financial officer, and our other executive officers who were serving as executive officers of the Company on December 31, 2023. These individuals are identified in the Summary Compensation Table and other compensation tables that follow this section, and are referred to throughout this report as our “named executive officers.”

Executive Summary and Overview of 2023 Compensation

Our Company’s long-term success depends on our ability to fulfill the expectations of our customers and clients in a competitive environment and deliver value to stockholders. To achieve these goals, it is critical that we are able to attract, motivate, and retain highly talented individuals at all levels of the organization that are committed to our values and objectives.

We strive to provide compensation that is (a) linked to stockholder value creation, (b) reflective of the overall performance of the Company and each individual executive, and (c) considerate of the competitive market levels of compensation needed to recruit, retain and motivate top executive talent, while remaining consistent with the other objectives.

Compensation Philosophy and Objectives

The Company’s executive compensation program is based on the same principles that guide us in establishing all of the Company’s compensation programs:

•

Compensation fosters the long-term focus required for the Company’s success. In general, the compensation of Company executives includes longer-term incentives because they are in a greater position to influence longer-term results.

•

Compensation reflects the level of job responsibility, individual performance, and Company performance. As employees progress to higher levels in the organization, an increasing proportion of their pay should be linked to Company performance and stockholder returns because those employees are more able to affect the Company’s results.

•

Compensation reflects the value of the job in the marketplace. To attract and retain a highly skilled work force, we must remain competitive with the pay of other premier employers who compete with us for talent.

•

While compensation programs and individual pay levels will always reflect differences in job responsibilities, geographies and marketplace considerations, the overall structure of the compensation and benefit programs should be broadly similar and equitable across the organization.

Overview of Executive Compensation

The Compensation Committee

Our Compensation Committee has primary responsibility for, among other things, determining our compensation philosophy, evaluating the performance of our executive officers, setting the compensation and other benefits of our executive officers, and considering the outcome of the advisory votes of stockholders on executive compensation.

To ensure alignment of compensation programs with the Company’s needs and goals, the Compensation Committee is informed by and responsive to the overall mission and strategies of the Company as determined by the full Board of Directors. As the strategic focus of the Company evolves, as for example toward commercialization of its products and profitability, the Compensation Committee has and will continue to adapt the Company’s compensation programs to meet these evolving needs.

The Compensation Committee also evaluates risks and rewards associated with the Company’s overall compensation philosophy and structure. To the extent our compensation programs provide for incentive−based compensation, the Compensation Committee evaluates whether these programs are designed

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to pay for performance, and thus encourage only appropriate risk-taking. These programs are also subject to oversight of the Compensation Committee and various functional departments of the Company to ensure that our employees, including our executive officers, are not encouraged to take excessive or unnecessary risks in managing our business.

Role of Executive Officers in Compensation Discussions

The Compensation Committee meets with our Chief Executive Officer in order to obtain recommendations with respect to the Company’s compensation programs and practices for executives and other employees. Management discusses with the Compensation Committee the practices that have been put in place to identify and mitigate, as necessary, potential risks. The Chief Executive Officer annually reviews the performance of each executive officer, other than himself. The Chief Executive Officer’s performance is reviewed annually by the Compensation Committee.

With support from market compensation data, performance reviews and other information, management makes recommendations to the Compensation Committee on the base salaries, bonus targets and equity compensation for the executive officers and other employees. The Compensation Committee takes management’s recommendations into consideration, but is not bound by management’s recommendations with respect to executive compensation.

While management attends certain meetings of the Compensation Committee, the Compensation Committee also holds executive sessions not attended by any members of management or by non−independent directors. The Compensation Committee annually reviews and recommends for approval to the full Board all elements of compensation of the Chief Executive Officer, and reviews, counsels, and makes recommendations regarding the compensation elements of other senior executives. The Compensation Committee also approves equity awards to all employees and directors of the Company.

Benchmarking Against Peer Companies

In February 2022, our Compensation Committee engaged the governance consulting firm of Morrow Sodali to assist with say-on-pay and the election of new directors.

In August 2022, our Compensation Committee engaged the compensation consulting firm of Pay Governance to assist the Committee in developing a peer group to benchmark executive compensation against other biotechnology, pharmaceutical, and life science companies with similar revenues and market capitalizations. Pay Governance then reviewed our current executive compensation program and made recommendations with respect to the design of our compensation program and future compensation decisions.

During 2023, Morrow Sodali and Pay Governance continued to provide assistance and recommendations to the Compensation Committee for determination of 2022 incentive awards earned, 2023 peer group benchmarking, and in transitioning to quantitative, finance-based metrics for future awards of incentive compensation. In addition, the Committee considered the Company’s most recent ISS Proxy Analysis Report and publicly available advisory materials relating to executive compensation benchmarking.

Elements of Executive Compensation

For 2023, the principal components of compensation for named executive officers were: (1) Base Salary, (2) Performance-Based Incentive Compensation, (3) Long-Term Equity Incentive Compensation, (4) Personal Benefits, and (5) Other Compensation. In determining the amount and relative allocation among each component of compensation for each named executive officer, the Compensation Committee considered, among other factors, each executive officer’s experience level and historical performance, compensation paid by companies comparable in size, data obtained from management’s recruitment activities, historical rates of executive compensation, Company revenues and financial outlook, and alignment with the Company’s overall compensation philosophy.

In connection with Mr. Firestone’s appointment as our Chief Executive Officer on November 28, 2023, the Compensation Committee recommended, and the Board approved, a cash target bonus of 75% of his base salary, or $319,000, subject to performance conditions to be determined by the Compensation Committee in

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its sole discretion. No performance-based or long-term incentive compensation was awarded to Mr. Firestone for the fiscal year ending December 31, 2023.

Base Salary

Base salaries are set at levels that the Compensation Committee deems to be sufficient to attract and retain highly talented executive officers capable of fulfilling the Company’s key objectives. Base salaries are also set with the goal of rewarding executive officers on a day−to−day basis for their time and services while encouraging them to strive for performance−based and long−term incentives.

The table below shows the base salary established by the Compensation Committee for each of our named executive officers for 2023 and 2024, and the percentage change compared to the prior fiscal year. Salary adjustments typically do not coincide with the beginning of the fiscal year, so the amounts shown below may differ from those shown in the 2023 Summary Compensation Table.

Name	2023 Base Salary			Percent Change vs. 2022 Base Salary		2024 Base Salary			Percent Change vs. 2023 Base Salary
Lawrence D. Firestone(1) Chief Executive Officer		$	425,000		N/A		$	425,000		0%
James A. Mish(2) Former Chief Executive Officer		$	486,675		3%			N/A		N/A
R. Hugh Kinsman(3) Former Chief Financial Officer		$	370,000		28%		$	296,000		(20)%
John J. Miller President of Tobacco		$	425,000		0%		$	212,500		(50)%
Peter Ferola(4) Former Chief Legal Officer		$	422,000		30%			N/A		N/A

(1)

Mr. Firestone was appointed as Chief Executive Officer on December 1, 2023.

(2)

Mr. Mish resigned as Chief Executive Officer effective August 1, 2023.

(3)

Mr. Kinsman resigned as Chief Financial Officer during April 2024.

(4)

Mr. Ferola was terminated in December 2023.

Performance-Based Incentive Compensation

Historically, the Compensation Committee has considered and in some cases established incentive bonus plans for other executive officers that align pay with performance. Because the Company has not in the Committee’s judgment achieved sufficient levels of revenues or profits, the Committee did not approve performance-based incentive compensation awards for named executive officers in 2023.

Long-Term Equity Incentive Program Compensation

Our 2021 Omnibus Incentive Plan, as amended and restated, authorizes the Company to grant various types of equity awards, including stock options and restricted stock units, as incentives for management to increase stockholder value. Equity awards are granted to executive officers as long-term incentives in order to align executives’ performance with the interests of the Company’s stockholders. In addition, the multi-year nature of the vesting periods of such awards encourages executive retention.

Our Compensation Committee has authority to determine eligible participants, the types of awards, and the terms and conditions of awards.

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The table below shows long-term equity incentive awards granted to named executive officers in 2023:

Name	RSU Grant Value			Number of Shares
Lawrence D. Firestone(1)			N/A		N/A
James A. Mish(2)		$	357,904		1,799
R. Hugh Kinsman		$	228,555		1,149
John Miller(3)			N/A		N/A
Peter Ferola(4)		$	256,149		1,288

(1)

Due to the timing of his appointment, Mr. Firestone was not awarded a long-term equity incentive award during 2023.

(2)

Mr. Mish’s long-term equity awards were forfeited upon his resignation.

(3)

In 2022, Mr. Miller received a performance award with vesting tied to milestones during 2023 and beyond. Accordingly, for 2023 no annual RSU was awarded.

(4)

Mr. Ferola’s long-term equity awards were forfeited upon his termination.

Upon review of the Company’s financial performance for 2023, the Committee determined to forego issuance of long-term equity incentive awards for 2024.

Personal Benefits

As employees, the executives were eligible to participate in health and welfare benefits, as offered to our general workforce, designed to attract and retain a skilled workforce in a competitive marketplace. These benefits help ensure that the Company has a healthy and focused workforce through reliable and competitive health and other personal benefits. We do not maintain any pension or non-qualified deferred compensation plans, but we do sponsor a 401(k)-plan pursuant to which we make a safe harbor non-elective contribution of 3% of the employee’s annual compensation, subject to certain wage maximums, to provide employees with the opportunity to save for retirement on a tax deferred basis. These benefits were considered in relation to total compensation packages, but did not materially impact decisions regarding other elements of executive officer compensation.

Other Compensation

On August 20, 2023, the Company entered into a Retention Agreement with R. Hugh Kinsman, the Company’s Chief Financial Officer, under which Mr. Kinsman would be entitled to certain cash payments if he remained an employee in Good Standing (as defined in Retention Agreement) through each applicable payment date. Pursuant to this agreement, the Company paid Mr. Kinsman two retention bonuses of $92,500 each on September 29 and October 31, 2023. Mr. Kinsman and the Company were also parties to an Employment Agreement entered into on June 15, 2022, which provided that if Mr. Kinsman’s employment were terminated by the Company without Cause (as defined in the Employment Agreement) he would be entitled to a severance benefit in the form of a continuation of his then-base salary for a period of 12 months (plus continuing health care coverage during such period). Both the Retention and Employment Agreements between Mr. Kinsman and the Company were mutually terminated on January 23, 2024 with no remaining obligations under either agreement.

On August 23, 2023, the Company entered into a Retention Agreement with John Miller, the Company’s President of the Tobacco Business and at that time its Interim Chief Executive Officer, under which Mr. Miller would be entitled to certain cash payments if he remained an employee in Good Standing (as defined in Retention Agreement) through each applicable payment date. Pursuant to this agreement, the Company paid Mr. Miller two retention bonuses of $92,500 each on September 29 and October 31, 2023. Upon the appointment of Lawrence D. Firestone as the Company’s Chief Executive Officer on November 28, 2023, Mr. Miller resumed his position of President of the Tobacco Business. Mr. Miller and the Company were also parties to an Employment Agreement entered into on November 11, 2022, which provided that if Mr. Miller’s employment were terminated by the Company without Cause (as defined in the Employment Agreement) he would be entitled to a severance benefit in the form of a continuation of his then-base salary for a period of

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12 months (plus continuing health care coverage during such period), as well as accelerated vesting of previously awarded restricted stock units. Both the Retention and Employment Agreements between Mr. Miller and the Company were mutually terminated on January 23, 2024 with no remaining obligations under either agreement.

Policy on Hedging Transactions

We prohibit our officers and directors from engaging in hedging transactions or arrangements designed to lock in the value of their company securities. This prevents our officers and directors from continuing to own company securities without having the full risks and rewards of ownership.

Recoupment/Clawback Policies

The Sarbanes-Oxley Act of 2002 subjects incentive compensation and stock sale profits of our CEO and CFO to forfeiture in the event of an accounting restatement resulting from any non-compliance, as a result of misconduct, with any financial reporting requirement under GAAP and SEC rules. We acknowledge the SEC’s new Rule 10D-1 regarding clawback policies and NASDAQ’s Listing Rule 5608(a) that went into effect on December 1, 2023. In anticipation of Listing Rule 5608(a), on June 22, 2023 the Board voted to adopt the 22nd Century Group, Inc. Compensation Recovery Policy in full compliance with Listing Rule 5608(a).

Compensation Committee Interlocks and Insider Participation

During the last fiscal year, no member of the Compensation Committee had a relationship with us that required disclosure under Item 404 of Regulation S-K. During the past fiscal year, none of our executive officers served as a member of the Board of Directors or Compensation Committee, or other committee serving an equivalent function, for any entity that has one (1) or more executive officers who served as members of our Board of Directors or our Compensation Committee. None of the members of our Compensation Committee is an officer or employee of our Company, nor have they ever been an officer or employee of our Company.

Compensation Committee Report

For the year ended December 31, 2023, the Compensation Committee reviewed and discussed the foregoing Compensation Discussion and Analysis with the Company’s management and Board of Directors. Based on this review and discussion, the Compensation Committee recommended to the Board that the Compensation Discussion and Analysis be included in this proxy statement.

Submitted by the members of the Compensation Committee
Lucille S. Salhany, Chair
Dr. Michael Koganov
Richard M. Sanders

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Executive Compensation

SUMMARY COMPENSATION TABLE FOR 2023

The following table summarizes the compensation of our NEOs for 2023. The amounts reported for stock awards may not represent the amounts that the NEOs will actually realize from the awards. Whether, and to what extent, a named executive officer realizes value will depend on our performance, stock price and continued employment.

Name and Principal Position	Year		Salary			Bonus(1)			Option Awards			Restricted Stock Unit Awards(2)			Non-Equity Incentive Compensation			All Other Compensation(3)			Total
Lawrence D. Firestone(4) Chief Executive Officer		2023		$	32,692		$	—		$	—		$	—		$	—		$	—		$	32,692
R. Hugh Kinsman(5) Former Chief Financial Officer		2023		$	358,600		$	185,000		$	—		$	228,555		$	—		$	19,432		$	791,497
R. Hugh Kinsman(5) Former Chief Financial Officer		2022		$	160,033		$	—		$	—		$	—		$	90,575		$	4,646		$	255,254
John J. Miller(6) President of Tobacco		2023		$	422,515		$	185,000		$	—		$	—		$	—		$	24,016		$	631,531
John J. Miller(6) President of Tobacco		2022		$	277,836		$	—		$	—		$	982,500		$	160,000		$	19,625		$	1,439,961
James A. Mish(7) Former Chief Executive Officer		2023		$	320,281		$	—		$	—		$	357,904		$	—		$	28,593		$	706,778
		2022		$	470,976		$	—		$	—		$	3,025,989		$	481,950		$	32,179		$	4,011,094
		2021		$	452,763		$	—		$	—		$	1,440,000		$	608,000		$	33,721		$	2,534,484
Peter Ferola(8) Former Chief Legal Officer		2023		$	388,140		$	250,000		$	—		$	256,149		$	—		$	25,647		$	919,936

(1)

Bonus amounts relate to amounts paid under retention agreements entered during August 2023 with respective NEO’s.

(2)

The fair value of each restricted stock unit is based on the stock price of the Company’s common stock on the grant date of the award.

(3)

All Other Compensation consists of the following:

Name	Year		Fringe Benefits*			Severance			Employer Contributions to Company 401(k) Plan			All Other Compensation Total
Lawrence D. Firestone		2023		$	—		$	—		$	—		$	—
R. Hugh Kinsman		2023		$	9,038		$	—		$	10,304		$	19,342
John J. Miller		2023		$	16,349		$	—		$	7,667		$	24,016
James A. Mish		2023		$	18,455		$	—		$	10,138		$	28,593
Peter Ferola		2023		$	16,882		$	—		$	8,765		$	25,647

Includes Company paid premiums for health insurance, dental insurance, group-term life insurance, and long-term disability insurance.

(4)

Mr. Firestone joined the Company in December 2023.

(5)

Mr. Kinsman joined the Company in May 2022.

(6)

Mr. Miller joined the Company in May 2022.

(7)

Mr. Mish was granted 1,288 shares at a grant date fair value of $199.04; all shares were forfeited upon resignation in 2023.

(8)

Mr. Ferola was granted 1,799 shares at a grant date fair value of $199.04; all shares were forfeited upon termination in 2023.

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Grants of Plan-Based Awards

GRANTS OF PLAN BASED AWARDS DURING 2023

As described above in the Compensation Discussion and Analysis, we granted restricted stock units to our NEOs in 2023. The following table sets forth information regarding all such awards:

Name	Grant Date		Date of Board Action		Restricted Stock Unit Awards: Number of Shares of Stock (#)(1)		Stock Option Awards: Number of Shares (#)		Exercise Price of Option Awards ($)		Grant Date Fair Value Restricted Stock Units, Stock Awards and Option Awards ($)(3)
Lawrence D. Firestone		—		—		—		—		—		$	—
R. Hugh Kinsman		3/14/2023		3/14/2023		1,149(2)		—		—		$	228,555
John J. Miller		—		—		—		—		—		$	—
James A. Mish		3/14/2023		3/14/2023		1,799(2)(4)		—		—		$	357,904
Peter Ferola		3/14/2023		3/14/2023		1,288(2)(5)		—		—		$	256,149

(1)

Number of shares is adjusted to reflect 1:15 reverse stock split that occurred July 5, 2023 and 1:16 reverse stock split that occurred on April 2, 2024

(2)

Represents RSUs which vest in equal increments over three years on March 14, 2024, 2025 and 2026, subject to continued service.

(3)

The fair value of each restricted stock unit is based on the stock price of the Company’s common stock on the grant date of the award.

(4)

Mr. Mish was granted 1,799 shares at a grant date fair value of $199.04; all shares were forfeited upon resignation in 2023.

(5)

Mr. Ferola was granted 1,288 shares at a grant date fair value of $199.04; all shares were forfeited upon termination in 2023.

Outstanding Equity Awards

The following table sets forth information about outstanding equity awards held on December 31, 2023 by our NEOs.

Name	Number of Securities Underlying Unexercised Options Exercisable (#)		Number of Securities Underlying Unexercised Options Unexercisable (#)		Option Exercise Price		Option Expiration Date		Equity Incentive Plan Awards: Number of Unearned Shares, Restricted Stock Units or Other Rights That Have Not Vested (#)		Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Restricted Stock Units or Other Rights That Have Not Vested ($)(3)
Lawrence D. Firestone		—		—		—		—		—		$	—
R. Hugh Kinsman		—		—		—		—		1,149(1)		$	3,419
John J. Miller		—		—		—		—		2,500(2)		$	7,440
James A. Mish		—		—		—		—		—		$	—
Peter Ferola		—		—		—		—		—		$	—

(1)

Represents RSUs which vest in equal increments over three years on March 14, 2024, 2025 and 2026 subject to continued service.

(2)

Represents performance shares, with one-half of such shares vesting on each of May 1, 2024 and 2025

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provided that our tobacco business plan revenue objectives and other performance requirements are satisfied at such times.

(3)

The amounts in this column are based on the closing stock price of the Company’s common stock on December 31, 2023. These amounts do not reflect the actual amounts that may be realized.

Option Exercises and Stock Vested in 2023

	Option Awards					Stock Awards
Name	Number of Shares Acquired on Exercise (#)		Value Realized on Exercise ($)			Number of Shares Acquired on Vesting (#)		Value Realized on Vesting ($)(1)
Lawrence D. Firestone		—		$	—		—		$	—
R. Hugh Kinsman		—		$	—		—		$	—
John J. Miller		—		$	—		625		$	124,350
James A. Mish		—		$	—		3,204		$	670,494
Peter Ferola		—		$	—		—		$	—

(1)

The value realized on vesting is based on the closing stock price of the Company’s common stock on the date of vesting or date of exercise. The amount does not reflect the actual amount that may be realized.

Pay versus Performance

The following table shows the past two (2) fiscal years’ total compensation for our named executive officers as set forth in the Summary Compensation Table, the “compensation actually paid” to our named executive officers (as determined under SEC rules), our total stockholder return (TSR), and our net income (loss).

SEC rules require certain adjustments be made to the Summary Compensation Table totals to determine Compensation Actually Paid as reported in the Pay Versus Performance Table. Compensation Actually Paid does not necessarily represent cash and/or equity value transferred to the applicable named executive officer without restriction, but rather is a valuation calculated under applicable SEC rules. In general, Compensation Actually Paid is calculated as summary compensation table total compensation adjusted to (a) include the value of any pension benefit (or loss) attributed to the past fiscal year, including on account of any amendments adopted during such year; and (b) include the fair market value of equity awards as of December 31, 2023 or, if earlier, the vesting date (rather than the grant date) and factor in dividends and interest accrued with respect to such awards. For purposes of the disclosure below, no pension valuation adjustments were required.

	Summary Compensation Table Total for Principal Executive Officer (PEO)(1)									Compensation Actually Paid to PEO(2)									Average Summary Compensation Table Total for Non-PEO NEOs(1)			Average Compensation Actually Paid to Non-PEO NEOs(3)			Value of Initial Fixed $100 Investment Based on Total Stockholder Return(4)			Net Income (Loss) ($000’s)(5)
Year	James A Mish			John J. Miller			Lawrence D. Firestone			James A. Mish			John J. Miller			Lawrence D. Firestone						Average Compensation Actually Paid to Non-PEO NEOs(3)						Net Income (Loss) ($000’s)(5)
2023		$	706,778		$	221,468		$	32,692		$	(529,515)		$	25,450		$	32,692		$	707,165		$	425,756		$	0.56		$	(140,775)
2022		$	4,011,094		$	N/A		$	N/A		$	1,495,978		$	N/A		$	N/A		$	888,087		$	411,232		$	42		$	(59,801)
2021		$	2,534,464		$	N/A		$	N/A		$	2,829,984		$	N/A		$	N/A		$	1,301,446		$	1,492,488		$	140		$	(32,609)

(1)

For each year represented through July 2023, James A. Mish was our principal executive officer (“PEO”) and our non-PEO NEOs for 2023 were R. Hugh Kinsman, John J. Miller, and Peter Ferola. Additionally, from July 2023 through November 2023, John J. Miller served as interim chief executive officer and PEO. For the period December 1, 2023 through December 31, 2023, our PEO was Lawrence D. Firestone. Our

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non-PEO NEO’s for 2022 were to John Franzino, Michael J. Zercher, R. Hugh Kinsman, John J. Miller and Richard Fitzgerald and for 2021 they were Richard Fitzgerald, John Franzino and Michael J. Zercher.

(2)

The amounts disclosed reflect the adjustments listed in the tables below to the amounts reported in the Summary Compensation Table for PEO:

Year	PEO	Less: Total Equity Compensation			Plus: Value Of Awards Granted During Current Year			Plus (Less): Year over Year Change in Fair Value Of Unvested Awards			Plus (Less): Vesting Date Value Of Awards that Vested During Current Year			Less: Value of Awards Forfeited During Current Year			Total Adjustments
2023	James A. Mish		$	(357,904)		$	—		$	—		$	(37,677)		$	(840,712)		$	(1,236,293)
2023	John. J. Miller		$	—		$	—		$	(191,179)		$	(4,839)		$	—		$	(196,019)
2023	Lawrence D. Firestone		$	—		$	—		$	—		$	—		$	—		$	—
2022	James A. Mish		$	(3,025,989)		$	1,272,573		$	(650,700)		$	(111,000)		$	—		$	(2,515,116)
2021	James A. Mish		$	(1,440,000)		$	1,390,500		$	—		$	345,000		$	—		$	295,500

(3)

The amounts disclosed reflect the adjustments listed in the tables below to the amounts reported in the Summary Compensation Table for our non-PEO NEO’s:

Year	Less: Total Equity Compensation			Plus: Value Of Awards Granted During Current Year			Plus (Less): Year over Year Change in Fair Value Of Unvested Awards			Plus (Less): Vesting Date Value Of Awards that Vested During Current Year			Plus: Value of Award Granted and Vested During Current Year			Total Adjustments
2023		$	(161,568)		$	1,140		$	(117,994)		$	(2,987)		$	—		$	(281,409)
2022		$	(396,380)		$	160,417		$	(52,056)		$	(227,908)		$	39,072		$	(476,855)
2021		$	(736,317)		$	648,900		$	159,275		$	119,184		$	—		$	191,042

(4)

Total Stockholder Return illustrates the value, as of the last day of the indicated fiscal year, of an investment of $100 in XXII common stock on January 1, 2021.

(5)

The dollar amounts reported represent the amount of net income (loss) reflected in our consolidated audited financial statements for the applicable year.

Analysis of the Information Presented in the Pay Versus Performance Table

Compensation Actually Paid and Net Income (Loss)

Due to the nature of our Company’s consolidated financial statements and primary focus on research and development for utilizing plant technologies to improve health and wellness with reduced nicotine tobacco, our Company has not historically utilized net income (loss) as a performance measure for our executive compensation program. From 2022 to 2023, our net loss increased and the Compensation Actually Paid to our PEO and Non-PEO NEOs decreased between those years.

PEO and Non-PEO NEO Compensation Actually Paid and Company Total Stockholder Return (“TSR”)

The following chart sets forth the relationship between Compensation Actually Paid to our PEO, the average of Compensation Actually Paid to our Non-PEO NEOs, and the Company’s TSR over the period covering fiscal years 2021 to 2023. A large component of our executive compensation is equity-based to align compensation with performance, but also includes other appropriate incentives such as cash bonuses that are designed to incentivize our executives to achieve annual corporate goals. We believe the equity-based compensation strongly aligns our PEO and Non-PEO NEOs’ interests with those of our stockholders to maximize long-term value and encourages long-term employment.

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Employment Agreements with Named Executive Officers

Currently, we do not have any employment agreements with our NEOs.

Compensation on Termination of Employment

Had a termination of Mr. Kinsman occurred on the last business day of 2023 under the circumstances described above, he would be entitled to a severance benefit in the form of a continuation of his then-base salary for a period of 12 months (plus continuing health care coverage during such period). The employment agreement between Mr. Kinsman and the Company was mutually terminated on January 23, 2024 with no remaining obligations.

Had a termination of Mr. Miller occurred on the last business day of 2023 under the circumstances described above, he would be entitled to a severance benefit in the form of a continuation of his then-base salary for a period of 12 months (plus continuing health care coverage during such period), as well as accelerated vesting of previously awarded restricted stock units. The employment agreement between Mr. Miller and the Company was mutually terminated on January 23, 2024 with no remaining obligations.

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PROPOSAL NO. 5
APPROVAL OF THE ~~ISSUANCE OF SHARES UPON EXERCISE~~AMENDMENT AND RESTATEMENT OF THE ~~INDUCEMENT WARRANTS IN ACCORDANCE WITH NASDAQ LISTING RULE 5635~~22ND CENTURY GROUP, INC. 2021 OMNIBUS INCENTIVE PLAN

~~General~~

~~On November 28, 2023, we commenced a warrant inducement offering with~~Our Board is seeking stockholder approval of the holders of our outstanding 31,779,654 warrants consisting of: (i) common stock purchase warrants issued on or about June 22, 2023; (ii) common stock purchase warrants issued on or about July 10, 2023; (iii) common stock purchase warrants issued on or about July 21, 2023;22nd Century Group, Inc. 2021 Omnibus Incentive Plan, as amended and ~~(iv) common stock purchase warrants issued on or about October 19, 2023 (collectively,~~restated (the “Plan”). We are amending and restating the ~~“Existing Warrants”), which were exercisable for an equal~~Plan primarily to increase the number of shares of our common stock ~~at an exercise price~~available for issuance under the Plan by 5,000,000 shares to continue to meet our compensation goals for current and future years. The amendment and restatement of ~~$0.525. In~~ the ~~warrant inducement offering,~~Plan is contingent on stockholder approval.

We use equity compensation as a key tool for attracting, motivating, and retaining talented individuals (not just senior executives). The Amended 2021 Omnibus Incentive Plan will allow us to utilize equity incentives in order to secure and retain the services of qualified personnel, especially as we ~~offered~~grow, and in light of the ~~holders a period~~highly competitive market for employee talent in which we operate, and to provide long-term incentives for alignment with the interests of ~~time (the “Inducement Period”) whereby we agreed~~our stockholders.

If the Plan as amended and restated is approved by our stockholders, it will continue to ~~issue new warrants (the “Inducement Warrants”)~~allow for the granting of equity and cash incentive awards to ~~purchase~~eligible individuals and will authorize the issuance of up to a ~~number~~total of 5,000,000 additional shares of our common stock pursuant to awards under the Plan. Awards under the Plan are intended to support the creation of long-term value and business returns for our stockholders. We believe that the Plan strikes an appropriate balance between rewarding performance and limiting stockholder dilution, while providing our Company with the flexibility to meet changing compensation needs. If the Plan as amended and restated is not approved by our stockholders, then the Plan as in effect prior to its amendment and restatement will remain in full force and effect.

Updated Share Information, Authorized Shares and Stock Price

As of April 16, 2024, there remained a total of 730,487 shares of common stock ~~equal~~available under the Plan, before any increase in available shares takes effect. As of April 16, 2024, there were outstanding awards under the Plan relating to ~~200%~~15,627 shares, consisting of one (1) option to purchase 10,534 shares with a weighted average exercise price of $437.52 and an average remaining term of 1.4 years, and two (2) restricted stock or restricted stock unit awards relating to 5,093 shares.

Our amended and restated certificate of incorporation authorizes the issuance of 250,000,000 shares of common stock. There were 6,046,560 shares of common stock issued and outstanding as of April 16, 2024 and the market value of a share of common stock as of that date was $1.65.

To determine the number of shares of common stock ~~issued pursuant~~ to be authorized under the ~~exercise by~~Plan, our Board considered the ~~holders~~number of shares remaining available under the ~~Existing Warrants during~~Plan, the ~~Inducement Period,~~needs of our Company for ~~cash, at~~shares, based on the current and expected future equity grant mix, and the potential dilution that awarding the requested shares may cause to existing stockholders.

Taking into consideration the factors described above, our Board determined that 5,000,000 additional shares should be authorized under the Plan. We estimate that the additional 5,000,000 shares that will be reserved for issuance under the Plan if the Plan is approved could result in a ~~reduced exercise price equal~~significant potential dilution to our existing stockholders, based on the ~~Nasdaq Minimum Price (as defined in the as defined in Nasdaq Listing Rule 5635(d)).~~

~~On November 28, 2023, we entered into warrant inducement agreements with certain holders of the Existing Warrants to purchase an aggregate of 13,032,182~~6,046,560 shares of common stock issued and outstanding as of April 16, 2024.

Because this proposal to approve the Plan does not contemplate the amount or timing of specific equity awards in the future, it is not possible to calculate with certainty the number of years of awards that will be available and the amount of subsequent dilution that may ultimately result from such awards.

Summary of the Terms of the Plan

The following is a summary of the material provisions of the Plan, a copy of which is attached hereto as Appendix B and incorporated by reference herein. This summary is qualified in its entirety by reference to the full and complete text of the Plan. Any inconsistencies between this summary and the text of the Plan will be governed by the text of the Plan.

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Purpose and Effective Date

The two complementary purposes of the Plan are (1) to attract, retain, focus and motivate our executives and other selected employees, directors, consultants and advisors; and (2) to increase stockholder value. Our Board amended and restated the Plan on April 19, 2024, contingent on approval by the Company’s stockholders. The Plan as amended and restated will become effective upon receiving stockholder approval at the 2024 Annual Meeting.

Administration and Eligibility

The Compensation Committee of our Board, or any successor committee with similar authority that the Board may appoint, which in either case consists of not less than two members of the Board who meet the “non-employee director” requirements of Rule 16b-3(b)(3) under the Securities Exchange Act of 1934 (the “Exchange Act”) (either referred to as the “Committee”) will administer the Plan and all awards (the “Administrator”). The Plan authorizes the Committee to interpret the provisions of the Plan and awards; prescribe, amend and rescind rules and regulations relating to the Plan; correct any defect, supply any omission, or reconcile any inconsistency in the Plan, any award or any agreement covering an award; and make all other determinations necessary or advisable for the administration of the Plan, in each case in its sole discretion. The Board may also administer the Plan to the extent it retains authority and responsibility as administrator of the Plan.

To the extent applicable law permits, the Board may delegate to another committee of the Board, or the Compensation Committee may delegate to one or more of our officers, any or all of their respective authority and responsibility as an administrator of the Plan. However, no such delegation is permitted with respect to stock-based awards made to any participant who is subject to the reporting requirements of Section 16(a) of the Exchange Act or the liability provisions of Section 16(b) of the Exchange Act at the time any such delegated authority or responsibility is exercised unless the delegation is to another committee of the Board consisting entirely of non-employee directors.

The Administrator may designate any of the following as a ~~reduced~~participant from time to time, to the extent of the Administrator’s authority: any officer or other employee of our Company or its affiliates; any individual who we or one of our affiliates has engaged to become an officer or employee; any consultant or advisor who provides services to the Company or its affiliates; or any director, including a non-employee director. Currently the persons eligible to participate in the Plan consist of approximately 60 employees and 6 non-employee directors.

Types of Awards

The Plan permits the grant of stock options (including incentive stock options), stock appreciation rights, restricted stock, restricted stock units, performance shares, performance units, annual cash incentives, long-term cash incentives, dividend equivalent units and other types of stock-based awards. These award types are described in further detail below.

Stock Subject to the Plan and Award Limits

Prior to the currently proposed amendment and restatement, the Plan provided that 730,487 shares of our common stock were reserved for issuance under the Plan. Other award types authorized by the Plan include nonqualified stock options, stock appreciation rights, restricted stock, restricted stock units, performance shares, performance units, annual cash incentives, long-term cash incentives, dividend equivalent units and other types of stock-based awards.

The Plan as amended and restated provides that an aggregate of 5,000,000 shares of our common stock will be reserved for issuance under the Plan, and that we may issue an aggregate of 5,000,000 shares upon the exercise of incentive stock options.

The number of shares reserved under the Plan will be depleted by the maximum number of shares, if any, that may be issuable under an award at the time of grant. In general, if an award granted under the Plan lapses, expires, terminates or is cancelled without the issuance of shares under the award, if it is determined during or at the conclusion of the term of an award that all or some portion of the shares under the award will not be

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issuable on the basis that the conditions for such issuance will not be satisfied, if shares are forfeited under an award or if shares are issued under any award and we reacquire them pursuant to rights reserved upon the issuance of the shares, then such shares will again be available for issuance under the Plan, except that shares reacquired pursuant to reserved rights may not be issued pursuant to incentive stock options. Shares not issued or delivered as a result of the net settlement of an outstanding option or stock appreciation right, shares tendered in payment of the exercise price of ~~$0.215. Pursuant~~an option, shares withheld to satisfy tax withholding obligations and shares purchased by us using proceeds from option exercises may not be re-credited to the ~~warrant inducement agreements,~~reserve.

The Plan also provides that any shares subject to awards granted under the ~~exercising holders~~2014 Omnibus Incentive Plan (the “Prior Plan”) that would be re-credited to the Prior Plan’s reserve if the Prior Plan was still in effect (but applying the provisions concerning share recycling of the ~~Existing Warrants~~Plan and the Prior Plan’s limits on re-crediting), then those shares will be available for the purpose of granting awards under the Plan, thereby increasing the reserve.

Subject to the Plan’s adjustment provisions, the maximum number of shares that may be subject to awards granted during any fiscal year to any non-employee director shall not exceed that number of shares that equates to a grant date fair value of, when added to any cash compensation received ~~26,064,364 Inducement Warrants~~by such non-employee director, $600,000 (the “Director Limit”). However, the Board of Directors may make exceptions to these limits in extraordinary circumstances as the Board may determine in its discretion, so long as the non-employee director receive such additional compensation may not participation in the decision to award such compensation.

Options

The Administrator will generally determine all terms and ~~we received aggregate gross~~conditions of each option. However, the grant date may not be any day prior to the date that the Administrator approves the grant, the exercise price may not be less than the fair market value of the shares subject to the option as determined on the date of grant (other than in the case of an option that is not an incentive stock option and that complies with Section 409A of the Internal Revenue Code of 1986, as amended (the “Code”)) and the option must terminate no later than ten years after the date of grant. Unless restricted by the Administrator, and subject to such procedures as the Administrator may specify, the payment of the exercise price of options may be made (1) by delivery of cash or other of our shares or other securities having a then fair market value equal to the purchase price of such shares; (2) by delivery to us or our designated agent of an executed irrevocable option exercise form together with irrevocable instructions to a broker-dealer to sell or margin a sufficient portion of the shares and deliver the sale or margin loan proceeds ~~of approximately $2.8 million from~~directly to us to pay for the exercise price; (3) by surrendering the right to receive shares otherwise deliverable to the participant upon exercise of the ~~Existing Warrants. If~~award having a fair market value at the time of exercise equal to the total exercise price; or (4) by any combination of (1), (2) and/or (3). Except to the extent otherwise set forth in an award agreement, a participant will have no rights as a holder of our common stock as a result of the grant of an option until the option is exercised, the exercise price and applicable withholding taxes are paid and the shares subject to the option are issued thereunder.

Stock Appreciation Rights

The Administrator will generally determine all terms and conditions of each stock appreciation right. A stock appreciation right is the right of a participant to receive cash in an amount, and/or common stock with a fair market value, equal to the appreciation of the fair market value of a share of our common stock during a specified period of time. However, the grant date may not be any day prior to the date that the Administrator approves the grant, the grant price may not be less than the fair market value of the shares subject to the stock appreciation right as determined on the date of grant (unless the stock appreciation right complies with Code Section 409A) and the stock appreciation right must terminate no later than ten years after the date of grant.

Performance and Stock Awards

The Administrator will generally determine all terms and conditions of each award of shares, restricted stock, restricted stock units, performance shares or performance units. Restricted stock means shares of our common stock that are subject to a risk of forfeiture, restrictions on transfer or both a risk of forfeiture and restrictions on transfer. Restricted stock unit means the right to receive a payment equal to the fair market value of one

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share of our common stock. Performance share means the right to receive shares of our common stock, including restricted stock, to the extent performance goals are achieved. Performance unit means the right to receive a payment valued in relation to a unit that has a designated dollar value or the value of which is equal to the fair market value of one or more shares of our common stock, to the extent performance goals are achieved. The terms and conditions that the Administrator will determine include the length of the vesting and/or performance period.

Incentive Awards

The Administrator has the authority to grant annual and long-term incentive awards. An incentive award is the right to receive a cash payment to the extent performance goals are achieved. The Administrator will determine all of the ~~holders participate~~terms and conditions of each incentive award, including the performance goals, the performance period, the potential amount payable and the timing of payment, provided that the Administrator must require that payment of all or any portion of the amount subject to the award is contingent on the achievement of one or more performance goals during the period the Administrator specifies, although the Administrator may specify that all or a portion of the goals are deemed achieved upon a participant’s death, disability or retirement, or such other circumstances as the Administrator may specify. For long-term incentive awards, the performance period must relate to a period of more than one fiscal year.

Dividend Equivalents and Dividends

In no event may dividends or dividend equivalent units be awarded with respect to options, stock appreciation rights or any other stock-based award that is not a grant of performance shares, performance units, restricted stock, restricted stock units or shares. For the avoidance of doubt, the Plan expressly prohibits the payment of dividends or dividend equivalent units on unvested awards for all equity award types.

If cash dividends are paid while shares of restricted stock are unvested, then such dividends will either, at the discretion of the Administrator, be (1) automatically reinvested as additional shares of restricted stock that are subject to the same terms and conditions, including the risk of forfeiture, as the original grant of restricted stock, or (2) paid in cash at the ~~warrant inducement offering, there would~~same time and the same extent that the restricted stock vests. For clarity, in no event will dividends be distributed to a participant unless, until and to the same extent as the underlying shares of restricted stock vest. The Administrator may grant dividend equivalent units only in tandem with restricted stock units, performance shares or performance units. For clarity, in no event will a participant receive payment with respect to a dividend equivalent unit unless, until and to the same extent as the tandem award vests and is paid.

Other Stock-Based Awards

The Administrator may grant to participants other types of awards that may be denominated or payable in, valued in whole or in part by reference to, or otherwise based on, shares of our common stock, either alone or in addition to or in conjunction with other awards, and payable in shares or cash. Subject to the limits of the Plan, an ~~aggregate~~award may include the issuance of ~~63,559,308 Inducement Warrants issued~~shares of unrestricted common stock, which may be awarded in payment of director fees, in lieu of cash compensation, in exchange for cancellation of a compensation right, as a bonus, or upon the attainment of performance goals or otherwise, or rights to acquire our common stock from us. The Administrator will generally determine all terms and conditions of the award, except that any award that provides for purchase ~~an equal~~rights must be priced at 100% of fair market value on the date of the award.

Minimum Vesting and Discretion to Accelerate

All awards granted under the Plan that may be settled in shares must have a minimum vesting period of one year from the date of grant, although that minimum vesting period will not apply to awards with respect to up to 5% of the total number of shares reserved under the Plan. For purposes of ~~common stock. As~~awards granted to non-employee directors, “one year” may mean the period of ~~December 6, 2023, we have issued~~time from one annual stockholders meeting to the next annual stockholders meeting as long as the period of time is not less than 50 weeks. The Administrator may accelerate the vesting of an ~~aggregate of 30,134,772 Inducement Warrants and received gross proceeds~~award or deem an award to be earned, in whole or in part, in the ~~warrant inducement offering~~event of ~~$3.2 million.~~a participant’s death, disability, retirement, or termination without cause, as provided in the Plan’s provisions concerning a change of control or upon any other event as determined by the Administrator in its sole and absolute discretion.

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Performance Goals

For purposes of the Plan, performance goals means any goals the Administrator establishes. Performance goals may, without limitation, relate to one or more of the following with respect to us or any one or more of our subsidiaries, affiliates or other business units: net sales; earnings before interest and taxes; earnings before interest, taxes, depreciation and amortization; fair market value of shares; basic earnings per share; diluted earnings per share; return on stockholder equity; return on average equity; return on average total capital employed; return on net assets employed before interest and taxes; economic value added; return on year-end equity; capital; cost of capital; cost of equity; cost of debt; taxes; market share; operating ratios; productivity measurements; revenue to budget compliance; net income to budget compliance; return on total awards reinvestment; net free cash flow; new sales; divisional profitability; customer satisfaction measurements; production quotas; project criteria or a combination of the foregoing.

As to each performance goal, unless otherwise determined by the Administrator at any time, the relevant measurement of performance will be computed in accordance with generally accepted accounting principles to the extent applicable. The Administrator may, at the time of establishing the performance goals, exclude the effects of (1) extraordinary, unusual and/or non-recurring items of gain or loss, (2) gains or losses on the disposition of a business, (3) changes in tax or accounting regulations or laws, or (4) the effect of a merger or acquisition. Performance goals may be expressed in terms of attaining a specified level of the particular criterion or the attainment of an increase or decrease (expressed as absolute numbers, averages and/or percentages) in the particular criterion or achievement in relation to a peer group or other index. The performance goals also may include a threshold level of performance below which no payment will be made (or no vesting will occur), levels of performance at which specified payments will be paid (or specified vesting will occur), and a maximum level of performance above which no additional payment will be made (or at which full vesting will occur). In addition, the Administrator may establish other performance goals and provide for other exclusions or adjustments not listed in the Plan.

Effect of Termination of Employment or Service on Awards

The ~~Inducement Warrants~~Administrator will have the discretion to determine, at the time an award is made to a participant or any time thereafter, the effect of the participant’s termination of employment or service with us or our affiliates on the award.

Transferability of Awards

Awards under the Plan generally will be nontransferable except (a) as otherwise determined by the Compensation Committee; (b) by will or the laws of descent and distribution; and (c) to the spouse, children, or grandchildren of a participant, or to trusts or partnerships for their benefit, under certain circumstances.

Adjustments

Under the terms of the Plan, if any of the following occurs:

•

We are involved in a merger or other transaction in which our common stock is changed or exchanged;

•

We subdivide or combine our common stock or declare a dividend payable in our common stock, other securities or other property;

•

We effect a cash dividend, the amount of which, on a per share basis, exceeds 10% of the fair market value of a share of our common stock at the time the dividend is declared, or we effect any other dividend or other distribution on our common stock in the form of cash, or a repurchase of shares of our common stock, that our Board of Directors determines is special or extraordinary in nature or that is in connection with a transaction that we characterize publicly as a recapitalization or reorganization involving our common stock; or

•

Any other event occurs, which, in the judgment of our Board of Directors or Compensation Committee necessitates an adjustment to prevent an increase or decrease in the benefits or potential benefits intended to be made available under the Plan;

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then the Administrator will, in a manner it deems equitable to prevent an increase or decrease in the benefits or potential benefits intended to be made available under the Plan and subject to certain provisions of the Code, adjust the number and type of shares of our common stock subject to the Plan and which may, after the event, be made the subject of awards; the number and type of shares of our common stock subject to outstanding awards; the grant, purchase or exercise price with respect to any award; and performance goals of an award.

No such adjustments may be authorized in the case of incentive stock options to the extent that such authority would cause the Plan to violate Code Section 422(b).

Without limitation, if there is a reorganization, merger, consolidation, combination or other similar corporate transaction or event, whether or not constituting a change of control (other than any such transaction in which we are the continuing corporation and in which the outstanding shares are not ~~exercisable~~being converted into or exchanged for different securities, cash or other property, or any combination thereof), the Administrator may substitute for each share then subject to an award and the shares subject to the Plan the number and kind of shares of stock, other securities, cash or other property to which holders of our common stock will be entitled in respect of each share pursuant to the transaction.

In the case of a stock dividend (other than a stock dividend declared in lieu of an ordinary cash dividend) or subdivision or combination of the shares (including a reverse stock split), if no action is taken by the Administrator, the adjustments described above will automatically be made.

In connection with any merger, consolidation, acquisition of property or stock, or reorganization, the Administrator may authorize the issuance or assumption of awards under the Plan.

Change of Control

Unless otherwise provided in an applicable employment, retention, change of control, severance, award or similar agreement, in the event of a change of control, the successor or purchaser in the change of control transaction may assume an award or provide a substitute award with similar terms and conditions and preserving the same benefits as the award it is replacing. If the awards are not so assumed or replaced, then unless otherwise determined by the board of directors prior to the date of the change of control, immediately prior to the date of the change of control:

•

each stock option or stock appreciation right that is then held by a participant who is employed by or in the service of us or one of our affiliates will become fully vested, and ~~until our stockholders approve (i) this Proposal 3~~all stock options and stock appreciation rights will be cancelled in exchange for a cash payment equal to ~~approve~~ the ~~issuance~~excess of the change of control price (as determined by the administrator) of the shares of common stock ~~underlying~~covered by the ~~Inducement Warrants~~stock option or stock appreciation right over the purchase or grant price of such shares of common stock under the award;

•

restricted stock, restricted stock units and share awards that are not vested will vest;

•

each holder of a performance share and/or performance unit that has been earned but not yet paid will receive cash equal to the value of the performance share and/or performance unit, and each performance share and/or performance unit for which the performance period has not expired will be cancelled in exchange for a cash payment equal to the value of the performance shares and/or performance units that would have been earned if the performance goals (as measured at the time of the change of control) were to continue to be achieved at the same rate through the end of the performance period, or if higher, assuming the target performance goals had been met at the time of such change of control, multiplied by a percentage based on the portion of the performance period that has elapsed as of the date of the change of control;

•

all incentive awards that are earned but not yet paid will be paid, and all incentive awards that are not yet earned will be cancelled in exchange for a cash payment equal to the amount that would have been due if the performance goals (measured at the time of the change of control) continued to be achieved through the end of the performance period at the higher of the then-current trend or target, multiplied by a percentage based on the portion of the performance period that has elapsed as of the date of the change of control;

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•

all dividend equivalent units that are not vested will vest and be paid in cash; and

•

all other awards that are not vested will vest, and if an amount is payable under such vested award, then such amount will be paid in cash based on the value of the award.

The terms of any awards that are subject to Code Section 409A will govern the treatment of such awards upon a change of control to the extent required for such awards to remain compliant with Code Section 409A, as applicable.

“Change of control” under the Plan means the occurrence of any one of the following:

•

Any person (other than an employee benefit plan of our Company or of any subsidiary and fiduciaries and certain other parties related to any of these plans) becomes the beneficial owner of our securities representing 35% or more of the combined voting power of our then outstanding securities;

•

We are merged or consolidated with any other corporation or other entity, other than a merger or consolidation which would result in our voting securities outstanding immediately prior thereto continuing to represent more than 65% of the combined voting power of our voting securities or the voting securities of such surviving entity outstanding immediately after such merger or consolidation, or we engage in a merger or consolidation effected to implement a recapitalization of our Company (or similar transaction) in which no person acquires 35% or more of the combined voting power of our then outstanding securities. Notwithstanding the foregoing, a merger or consolidation involving our Company will not be considered a change of control if we are the surviving corporation and shares are not converted into or exchanged for stock or securities of any other corporation, cash or any other thing of value, unless persons who beneficially owned shares outstanding immediately prior to such transaction own beneficially less than a majority of our outstanding voting securities immediately following the merger or consolidation;

•

We or any of our affiliates sell, assign or otherwise transfer assets in a transaction or series of related transactions, if the aggregate market value of the assets so transferred exceeds 35% of our consolidated book value, determined by us in accordance with generally accepted accounting principles, measured at the time at which such transaction occurs or the first of such series of related transactions occurs; provided, however, that such a transfer effected pursuant to a spin-off or split-up where our stockholders retain ownership of the transferred assets proportionate to their pro rata ownership interest in our Company will not be a change of control;

•

We dissolve and liquidate substantially all of our assets; or

•

At any time when the “continuing directors” cease to constitute a majority of our Board of Directors. For this purpose, a “continuing director” means the individuals who, at the effective date of the Plan, constitute the Board and any new directors (other than directors designated by a person who has entered into an agreement with us to effect a change of control transaction) whose appointment to the Board or nomination for election by our stockholders was approved by a vote of at least two-thirds of the then-serving continuing directors.

If an award is considered deferred compensation subject to the provisions of Code Section 409A, then the Administrator may include an amended definition of “change of control” in the award agreement issued with respect to such award as necessary to comply with, or as necessary to permit a deferral under, Code Section 409A.

The Plan does not provide for a “gross-up” for any excise taxes imposed on golden parachute payments under Code Section 4999. Rather, except to the extent the participant has in effect an employment or similar agreement with us or any affiliate or is subject to a policy that provides for a more favorable result to the participant, if any payments or benefits paid by us pursuant to the Plan would cause some or all of such payments or benefits in conjunction with any other payments or benefits in connection with a change of control to be subject to the tax imposed by Code Section 4999, then these payments will either be cut back to a level below the amount triggering the tax or be delivered in full, whichever will provide the greater after-tax benefit to the participant.

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Termination and Amendment

The Plan will expire on the tenth anniversary of the most recent stockholder approval, subject to the Board’s right to terminate the Plan at any time. If approved, this proposal constitutes stockholder approval. In addition, the Board or the Administrator may amend the Plan at any time, except:

•

Our Board of Directors must approve any amendment to the Plan if we determine such approval is required by prior action of the Board, applicable ~~Nasdaq rules~~corporate law or any other applicable law;

•

Stockholders must approve any amendment to the Plan if we determine that such approval is required by Section 16 of the Exchange Act, the listing requirements of any principal securities exchange or market on which our common stock is then traded, or any other applicable law; and ~~(ii) a proposal~~

Stockholders must approve any further amendment to ~~amend our charter to increase~~the Plan that materially increases the number of shares of common stock ~~authorized~~reserved under the Plan, that would materially expand the group of individuals eligible to become participants or that diminishes the provisions prohibiting repricing or backdating stock options and stock appreciation rights.

The Administrator generally may modify, amend or cancel any award or waive any restrictions or conditions applicable to any award or the exercise of the award. Any modification or amendment that materially diminishes the rights of the participant or any other person who may have an interest in the award, or that cancels any award, will be effective only if agreed to by that participant or other person. The Administrator does not need to obtain participant or other interested party consent, however, for ~~issuance (Proposal 2)~~the adjustment or cancellation of an award pursuant to the adjustment provisions of the Plan or the modification of an award to the extent deemed necessary to comply with any applicable law or the listing requirements of any principal securities exchange or market on which our common stock is then traded, to the extent the Administrator deems necessary to preserve favorable accounting or tax treatment of any award for us, or to the extent the Administrator determines that the action does not materially and adversely affect the value of an award or that such action is in the best interest of the affected participant or any other person(s) with an interest in the award.

The authority of the Administrator to terminate or modify the Plan or awards will extend beyond the termination date of the Plan. In addition, termination of the Plan will not affect the rights of participants with respect to awards previously granted to them, and all unexpired awards will continue in force after termination of the Plan except as they may lapse or be terminated by their own terms and conditions.

Cancellation, Disgorgement and Recoupment of Awards

The Compensation Committee may cancel an award or require a participant to return to us any compensation received under an award in certain circumstances, such as if the participant is terminated for cause or breaches any restrictive covenants, such as a non-compete, with us. In addition, all awards will be subject to any recoupment or clawback policy that we adopt from time to time.

Repricing Prohibited

Neither the Administrator nor any other person may: (1) amend the terms of outstanding stock options or stock appreciation rights to reduce the exercise price of such outstanding stock options or stock appreciation rights; (2) cancel outstanding stock options or stock appreciation rights in exchange for stock options or stock appreciation rights with an exercise price that is less than the exercise price of the original stock options or stock appreciation rights; or (3) cancel outstanding stock options or stock appreciation rights with an exercise price above the current share price in exchange for cash or other securities.

Backdating Prohibited

The Administrator may not grant a stock option or stock appreciation right with a grant date that is effective prior to the date the Administrator takes action to approve such award.

Foreign Participation

To assure the viability of awards granted to participants employed or residing in foreign countries, the Administrator may provide for such special terms as it may consider necessary or appropriate to accommodate

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differences in local law, tax policy, accounting or custom. Moreover, the Administrator may approve such supplements to, or amendments, restatements or alternative versions of, the Plan as it determines is necessary or appropriate for such purposes. Any such amendment, restatement or alternative versions that the Administrator approves for purposes of using the Plan in a foreign country will not affect the terms of the Plan for any other country.

Certain Federal Income Tax Consequences

The following summarizes certain federal income tax consequences relating to the Plan. The summary is based upon the laws and regulations in effect as of the date of this proxy statement and does not purport to be a complete statement of the law in this area. Furthermore, the discussion below does not address the tax consequences of the receipt or exercise of awards under foreign, state or local tax laws, and such tax laws may not correspond to the federal income tax treatment described herein. The exact federal income tax treatment of transactions under the Plan will vary depending upon the specific facts and circumstances involved and participants are advised to consult their personal tax advisors with regard to all consequences arising from the grant or exercise of awards and the disposition of any acquired shares.

Stock Options

The grant of a stock option under the Plan will create no income tax consequences to us or to the recipient. A participant who is granted a non-qualified stock option will generally recognize ordinary compensation income at the time of exercise in an amount equal to the excess of the fair market value of our common stock at such time over the exercise price. We will generally be entitled to a deduction in the same amount and at the same time as the participant recognizes ordinary income. Upon the participant’s subsequent disposition of the shares of our common stock received with respect to such stock option, the participant will recognize a capital gain or loss (long-term or short-term, depending on the holding period) to the extent the amount realized from the sale differs from the tax basis (i.e., the fair market value of our common stock on the exercise date).

In general, a participant will recognize no income or gain as a result of the exercise of an incentive stock option, except that the alternative minimum tax may apply. Except as described below, the participant will recognize a long-term capital gain or loss on the disposition of our common stock acquired pursuant to the exercise of an incentive stock option and we will not be allowed a deduction. If the participant fails to hold the shares of our common stock acquired pursuant to the exercise of an incentive stock option for at least two years from the grant date of the incentive stock option and one year from the exercise date, then the participant will recognize ordinary compensation income at the time of the disposition equal to the lesser of the gain realized on the disposition and the excess of the fair market value of the shares of our common stock on the exercise date over the exercise price. We will generally be entitled to a deduction in the same amount and at the same time as the participant recognizes ordinary income. Any additional gain realized by the participant over the fair market value at the time of exercise will be treated as a capital gain.

Stock Appreciation Rights

The grant of a stock appreciation right under the Plan will create no income tax consequences to us or to the recipient. A participant who is granted a stock appreciation right will generally recognize ordinary compensation income at the time of exercise in an amount equal to the excess of the fair market value of our common stock at such time over the grant price. We will generally be entitled to a deduction in the same amount and at the same time as the participant recognizes ordinary income. If the stock appreciation right is settled in shares of our common stock, upon the participant’s subsequent disposition of such shares, the participant will recognize a capital gain or loss (long-term or short-term, depending on the holding period) to the extent the amount realized from the sale differs from the tax basis (i.e., the fair market value of our common stock on the exercise date).

Restricted Stock

Generally, a participant will not recognize income and we will not be entitled to a deduction at the time an award of restricted stock is made under the Plan, unless the participant makes the election described below. A participant who has not made such an election will recognize ordinary income at the time the restrictions on

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the stock lapse in an amount equal to the fair market value of the restricted stock at such time. We will generally be entitled to a corresponding deduction in the same amount and at the same time as the participant recognizes income. Any otherwise taxable disposition of the restricted stock after the time the restrictions lapse will result in a capital gain or loss (long-term or short-term, depending on the holding period) to the extent the amount realized from the sale differs from the tax basis (i.e., the fair market value of our common stock on the date the restrictions lapse). Dividends paid in cash and received by a participant prior to the time the restrictions lapse will constitute ordinary income to the participant in the year paid and we will generally be entitled to a corresponding deduction for such dividends. Any dividends paid in stock will be treated as an award of additional restricted stock subject to the tax treatment described herein.

A participant may, within 30 days after the date of the award of restricted stock, elect to recognize ordinary income as of the date of the award in an amount equal to the fair market value of such restricted stock on the date of the award (less the amount, if any, the participant paid for such restricted stock). If the participant makes such an election, then we will generally be entitled to a corresponding deduction in the same amount and at the same time as the participant recognizes income. If the participant makes the election, then any cash dividends the participant receives with respect to the restricted stock will be treated as dividend income to the participant in the year of payment and will not be deductible by us. Any otherwise taxable disposition of the restricted stock (other than by forfeiture) will result in a capital gain or loss. If the participant who has made an election subsequently forfeits the restricted stock, then the participant will not be entitled to claim a credit for the tax previously paid. In addition, we would then be required to include as ordinary income the amount of any deduction it originally claimed with respect to such shares.

Restricted Stock Units

A participant will not recognize income and we will not be entitled to a deduction at the time an award of a restricted stock unit is made under the Plan. Upon the participant’s receipt of shares (or cash) at the end of the restriction period, the participant will recognize ordinary income equal to the amount of cash and/or the fair market value of the shares received, and we will be entitled to a ~~reverse~~corresponding deduction in the same amount and at the same time. If the restricted stock ~~split without adjusting~~units are settled in whole or in part in shares, upon the ~~authorized~~participant’s subsequent disposition of the shares the participant will recognize a capital gain or loss (long-term or short-term, depending on the holding period) to the extent the amount realized upon disposition differs from the shares’ tax basis (i.e., the fair market value of the shares on the date the participant received the shares).

Performance Shares

The grant of performance shares will create no income tax consequences for us or the participant. Upon the participant’s receipt of shares at the end of the applicable performance period, the participant will recognize ordinary income equal to the fair market value of the shares received, except that if the participant receives shares of restricted stock in payment of performance shares, recognition of income may be deferred in accordance with the rules applicable to restricted stock as described above. In addition, the participant will recognize ordinary compensation income equal to the dividend equivalents paid on performance shares prior to or at the end of the performance period. We will generally be entitled to a deduction in the same amount and at the same time as the participant recognizes income. Upon the participant’s subsequent disposition of the shares, the participant will recognize a capital gain or loss (long-term or short-term depending on the holding period) to the extent the amount realized from the disposition differs from the shares’ tax basis (i.e., the fair market value of the shares on the date the participant received the shares).

Performance Units

The grant of a performance unit will create no income tax consequences to us or the participant. Upon the participant’s receipt of cash and/or shares at the end of the applicable performance period, the participant will recognize ordinary income equal to the amount of cash and/or the fair market value of the shares received, and we will be entitled to a corresponding deduction in the same amount and at the same time. If performance units are settled in whole or in part in shares, upon the participant’s subsequent disposition of the shares the participant will recognize a capital gain or loss (long-term or short-term, depending on the holding period) to the extent the amount realized upon disposition differs from the shares’ tax basis (i.e., the fair market value of the shares on the date the participant received the shares).

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Incentive Awards

A participant who is paid an incentive award will recognize ordinary income equal to the amount of cash paid, and we will generally be entitled to a corresponding income tax deduction.

Dividend Equivalent Units

A participant who is paid a dividend equivalent with respect to an award will recognize ordinary income equal to the value of cash or common stock paid, and we will be entitled to a corresponding deduction in the same amount and at the same time.

Section 162(m) Limit on Deductibility of Compensation

Section 162(m) of the Code limits the deduction we can take for compensation, including compensation arising from awards under the Plan, paid to covered employees to $1,000,000 per person per year. The covered employees for any fiscal year generally include any employee (i) who served as our chief executive officer or chief financial officer at any point during the fiscal year, (ii) whose compensation was otherwise required to be included in our proxy statement by reason of being among our three highest compensated officers for the fiscal year, or (iii) who was a covered employee for any preceding fiscal year beginning after December 31, 2016. The American Rescue Plan Act of 2021 will, for taxable years beginning after December 31, 2026, include as covered employees an additional five employees who are among the most highly compensated.

Code Sections 409A and 280G

Awards under the Plan may constitute, or provide for, a deferral of compensation under Section 409A of the Code. If the requirements of Code Section 409A are not complied with, then holders of such awards may be taxed earlier than would otherwise be the case (e.g., at the time of vesting instead of the time of payment) and may be subject to an additional 20% penalty tax and, potentially, interest and penalties. The Plan is intended to permit compliance with Code Section 409A and the Department of Treasury regulations and other interpretive guidance that may be issued pursuant to Code Section 409A. To the extent that we determine that any award granted under the Plan is subject to Code Section 409A, the award agreement evidencing such award is expected generally to incorporate the terms and conditions required by Code Section 409A. The Plan and any applicable awards may be modified to exempt the awards from Code Section 409A or comply with the requirements of Code Section 409A.

Code Sections 280G and 4999 may limit our income tax deduction and impose an excise tax on golden parachute payments to participants in the event there is a change of control of our Company. The Plan does not provide for a “gross-up” for any excise taxes imposed on golden parachute payments under Code Section 4999. Rather, except to the extent the participant has in effect an employment or similar agreement with us or any affiliate or is subject to a policy that provides for a more favorable result to the participant, if any payments or benefits paid by us pursuant to the Plan would cause some or all of such payments or benefits in conjunction with any other payments or benefits in connection with a change of control to be subject to the tax imposed by Code Section 4999, then these payments will either be cut back to a level below the amount triggering the tax or be delivered in full, whichever will provide the greater after-tax benefit to the participant. Accordingly, some or all of the amount which would otherwise be deductible may not be deductible with respect to benefits under the Plan that are contingent on or otherwise provided in connection with a change of control of our Company.

New Plan Benefits

The awards that may be granted under the Plan in the future to the executive officers or non-employee directors named in this proxy statement or to other officers, non-employee directors, employees, or other persons cannot be determined at this time. Our Board of Directors, along with management, will make such determinations from time to time.

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Equity Compensation Plan Information

The following table summarizes the number of shares of common stock ~~(Proposal 1) ((i)~~to be issued upon exercise of outstanding options and ~~(ii) collectively, “Stockholder Approval”).~~vesting of restricted stock units under the Plan, our prior 2010 plan and the Prior Plan, the weighted-average exercise price of such stock options, and the number of securities available to be issued under the Plan as of December 31, 2023:

	Number of securities to be issued upon exercise of outstanding options, and restricted stock units, (a)		Weighted average exercise price of outstanding options (b)			Number of securities remaining available for issuance under equity compensation plans (excluding securities reflected in column (a)) (c)
Equity compensation plans approved by security holders		23,410(1)		$	421.51		606,406
Equity compensation plans not approved by security holders		—			N/A		—
Total		23,410			—		606,406(2)

(1)

Number of outstanding options are 13,729 and number of unvested restricted stock units are 9,681.

(2)

Consists of shares available for award under the Plan.

Our Board of Directors recommends a vote “FOR” the approval of the amendment and restatement of the 22nd Century Group, Inc. 2021 Omnibus Incentive Plan.

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PROPOSAL NO. 6
APPROVAL OF THE ISSUANCE OF THE SHARES OF COMMON STOCK UPON EXERCISE OF THE WARRANTS DATED APRIL 9, 2024 PURSUANT TO NASDAQ LISTING RULE 5635

The ~~Inducement~~board of directors has approved and recommends to the stockholders a proposal to approve the issuance of the Warrants ~~will be exercisable~~(defined below) dated April 9, 2024 (the “Warrants Shares”) pursuant to Rule 5635(d) of the Nasdaq Stock Market for the potential issuance of more than 19.99% of our outstanding common stock at ~~any time~~below the Minimum Price under Nasdaq rules.

General

As previously disclosed on ~~or after~~a current report on Form 8-K filed with SEC on April 8, 2024, the ~~Stockholder Approval date, have an expiration date~~Company and certain investors (the “Investors”) entered into a securities purchase agreement (the “Securities Purchase Agreement”) on April 8, 2024 relating to, among other things, the private placement of ~~five years from the Stockholder Approval date, and have~~warrants to purchase up 1,980,000 shares of common stock (the “Warrants”) at an exercise price ~~equal~~of $2.14 per share, which exercise price is subject to adjustment in certain circumstances, including upon any subsequent equity sales at a price per share lower than the then effective exercise price of such warrants, then such exercise price shall be lowered to such price at which the shares were offered. A copy of the Securities Purchase Agreement and the Warrants are attached as exhibits to the ~~Nasdaq Minimum Price (as defined in~~Company’s Form 8-K filed with the ~~as defined in Nasdaq Listing Rule 5635(d)).~~ SEC on April 9, 2024.

The ~~exercise prices~~Warrants are exercisable after the receipt of stockholder approval and expire on the Inducement Warrants will be subject to appropriate adjustment in the event of recapitalization events, stock dividends, stock splits, stock combinations, reclassifications, reorganizations or similar events affecting the Company’s common stock. In addition, the Inducementdate that is five (5) years thereafter. The Warrants are subject to adjustment in certain circumstances, including upon any subsequent equity sales at a price per share lower than the then effective exercise price of such ~~Inducement Warrants,~~warrants, then such exercise price shall be lowered to such price at which the shares were offered. Section 3(b) of the ~~Inducement~~ Warrants provides as follows:

Subsequent Equity Sales. If the Company or any Subsidiary thereof, as applicable, at any time while this Warrant is outstanding, shall sell, enter into an agreement to sell or grant any option to purchase, or sell or grant any right to reprice, or otherwise dispose of or issue (or announce any offer, sale, grant or any option to purchase or other disposition) any Common Stock or Common Stock Equivalents, at an effective price per share less than the Exercise Price then in effect (such lower price, the “Base Share Price” and such issuances collectively, a “Dilutive Issuance”) (it being understood and agreed that if the holder of the Common Stock or Common Stock Equivalents so issued shall at any time, whether by operation of purchase price adjustments, reset provisions, floating conversion, exercise or exchange prices or otherwise, or due to warrants, options or rights per share which are issued in connection with such issuance, be entitled to receive shares of Common Stock at an effective price per share that is less than the Exercise Price, such issuance shall be deemed to have occurred for less than the Exercise Price on such date of the Dilutive Issuance at such effective price), then simultaneously with the consummation (or, if earlier, the announcement) of each Dilutive Issuance the Exercise Price shall be reduced and only reduced to equal the Base Share Price. Notwithstanding the foregoing, no adjustments shall be made, paid or issued under this Section 3(b) in respect of an Exempt Issuance. The Company shall notify the Holder, in writing, no later than the Trading Day following the issuance or deemed issuance of any Common Stock

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or Common Stock Equivalents subject to this Section 3(b), indicating therein the applicable issuance price, or applicable reset price, exchange price, conversion price and other pricing terms (such notice, the “Dilutive Issuance Notice”). For purposes of clarification, whether or not the Company provides a Dilutive Issuance Notice pursuant to this Section 3(b), upon the occurrence of any Dilutive Issuance, the Holder is entitled to receive a number of Warrant Shares based upon the Base Share Price regardless of whether the Holder accurately refers to the Base Share Price in the Notice of Exercise. If the Company enters into a Variable Rate Transaction, the Company shall be deemed to have issued Common Stock or Common Stock Equivalents at the lowest possible price, conversion price or exercise price at which such securities may be issued, converted or exercised provided; however that the foregoing shall not apply to an “at-the-market” offering program or similar offering facility unless and until the Company actually sells shares under such program at a price per share less than the Exercise Price then in effect.

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Reasons for Stockholder Approval

InThe Securities Purchase Agreement provides that the ~~warrant inducement offering, we agreed to use commercially reasonable efforts to~~Company shall hold an annual or a special meeting of stockholders ~~within ninety (90)~~on or prior to the date that is 90 days following the Closing Date (as defined in the Securities Purchase Agreement) for the purpose of obtaining approval as may be required by the applicable rules and regulations of the Nasdaq Capital Market (or any successor entity) from the stockholders of the Company with respect to ~~obtain~~ the issuance of the Warrants and the Warrant Shares in connection with the Securities Purchase Agreement (“Stockholder ~~Approval.~~Approval”).

~~In addition, our~~Our common stock is listed on the Nasdaq Capital Market under the symbol “XXII,” and we are subject to the Nasdaq listing standards and rules. Under Rule 5635(d) of the Nasdaq Stock Market, stockholder approval is required in connection with a transaction, other than a public offering, at a price below the Minimum Price (as defined under Nasdaq rules) involving the sale, issuance or potential issuance by the Company of common stock (or securities convertible into or exercisable for common stock), which equals 20% or more of the common stock or 20% or more of the voting power outstanding before the issuance. ~~The Inducement~~Section 3(b) of the Warrants could ~~potentially~~ result in the potential issuance of more than ~~a 20% Issuance (as defined in Nasdaq rules)~~19.99% of ~~shares of~~our outstanding common stock at ~~a price~~ below the Minimum Price ~~and would violate Rule 5635~~under Nasdaq rules without approval of our stockholders.

Use of Proceeds

The Company intends to use the net proceeds, if any, from any ~~Inducement~~ Warrant ~~exercises~~cash exercise for accelerating the consumer use data for VLN® among adult smokers, and accretive structural changes to streamline operations as the VLN® business achieves greater scale and general corporate purposes.

Possible Effects of the Proposal

If the stockholders do not approve this Proposal 3,6, then the ~~Inducement~~ Warrants will not ~~become~~be exercisable. ~~However, we~~The Company, as provided in the Securities Purchase Agreement will ~~also~~ be obligated to incur additional management resources and expenses to call and hold a meeting every 90 days thereafter to seek such stockholder approval until the date Stockholder Approval is obtained. Additionally, the failure to obtain Stockholder Approval may discourage future investors from engaging in future financings with us. If these consequences occur, we may have difficulty finding alternative sources of capital to fund our operations in the future on terms favorable to us or at all. We can provide no assurance that we would be successful in raising funds pursuant to additional equity or debt financings.

If the stockholders approve this Proposal 3,6, the ~~Inducement~~ Warrants ~~will be exercisable,~~shall become immediately exercisable. The Warrants could also have a reduced exercise price upon a dilutive issuance, which could result in substantial dilution to our stockholders.

~~Interests of Directors and Executive Officers~~

~~None.~~

Our Board of Directors recommends that the stockholders vote “FOR” Proposal 36 to
approve the issuance of the shares of common stock upon exercise of the ~~Inducement Warrants.~~Warrants pursuant to Rule 5635(d) of the Nasdaq Stock Market.

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PROPOSAL ~~FOUR:~~ NO. 7
APPROVAL OF THE VOLUNTARY CONVERSION OPTION IN THE DEBENTURES DATED MARCH 3, 2023, AS AMENDED DECEMBER 22, 2023, PURSUANT TO RULES 5635(B) AND 5635(D) OF THE NASDAQ STOCK MARKET

The Board of Directors has approved and recommends to the stockholders a proposal to approve the Voluntary Conversion Option (defined below) in the Debentures dated March 3, 2023, as amended on December 22, 2023, pursuant to Rule 5635(b) for a potential change in control of the Company, and Rule 5635(d) of the Nasdaq Stock Market for the potential issuance of more than 19.99% of our outstanding common stock at below the Minimum Price under Nasdaq rules.

Overview

On March 3, 2023, the Company entered into that certain Securities Purchase Agreement (the “SPA”) with JGB Partners, LP (“JGB Partners”), JGB Capital, LP (“JGB Capital”) and JGB Capital Offshore Ltd. (“JGB Offshore” and collectively with JGB Partners and JGB Capital, the “Holders”) and JGB Collateral, LLC, as collateral agent for the Holders (the “Agent”). Pursuant to the SPA, the Holders purchased (i) 7% Original Issue Discount Senior Secured Debentures (the “Debentures”) of the Company and (ii) warrants to purchase up to 20,644 shares (after the redemption of 10,417 warrants) shares of the Company’s common stock, par value $0.00001 per share.

As previously disclosed on a current report Form 8-K filed with the U.S. Securities and Exchange Commission, or SEC, on December 22, 2023, the Company, the Holders and the Agent entered into an Amendment Agreement (the “JGB Amendment”) pursuant to which the Holders and the Agent consented to the sale of the Company’s hemp/cannabis business. In consideration of the Holders and the Agents’ consent, the Company agreed to amend the Debentures to allow the Holders to voluntarily convert the Debentures, in whole or in part, into shares of the Company’s common stock (“Voluntary Conversion Option”) on the earlier of (i) June 30, 2024 and (ii) the public announcement of a Fundamental Transaction at a conversion price equal to the lower of (x) $16.00 per share and (y) the closing sale price of the Company’s common stock on June 29, 2024 (the “Conversion Price”), along with other concessions.

The Voluntary Conversion Option is subject to the approval of the Company’s stockholders and the Company is required pursuant to the JGB Amendment to use its commercially reasonable efforts to obtain such approval.

Section 5(b) of the Amended Debenture provides as follows:

Voluntary Conversion.

(1)

Voluntary Conversion. Commencing on the earlier of (i) June 30th, 2024 and (ii) the public announcement of a Fundamental Transaction (including a pending Fundamental Transaction), and thereafter from time to time until this Debenture is no longer outstanding, this Debenture shall be convertible, in whole or in part, into shares of Common Stock at the option of the Holder, subject to the conversion limitations set forth in Section 5(h). The Holder shall effect conversions by delivering to the Company a Notice of Conversion, the form of which is attached hereto as Annex B (each, a “Notice of Conversion”), specifying therein the principal amount of this Debenture to be converted and the date on which such conversion shall be effected (such date, the “Conversion Date”). If no Conversion Date is specified in a Notice of Conversion, the Conversion Date shall be the date that such Notice of Conversion is deemed delivered hereunder. No ink-original Notice of Conversion shall be required, nor shall any medallion guarantee (or other type of guarantee or notarization) of any Notice of Conversion form be required. To effect conversions hereunder, the Holder shall not be required to physically surrender this Debenture to the Company unless the entire principal amount of this Debenture, plus all accrued and unpaid interest thereon, has been so converted. Conversions hereunder shall have the effect of lowering the outstanding principal amount of this Debenture in an amount equal to the applicable conversion. The Holder and the Company shall maintain records showing the principal amount(s) converted and the date of such conversion(s). In the event of any dispute or discrepancy, the records of the Holder shall be controlling and determinative in the absence of manifest error. The Holder, and any assignee by acceptance of this Debenture, acknowledge and agree that, by reason of the provisions of this paragraph, following conversion of

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a portion of this Debenture, the unpaid and unconverted principal amount of this Debenture may be less than the amount stated on the face hereof.

(2)

Conversion Price. The conversion price in effect on any Conversion Date shall be equal to the lower of (i) $16.00 per share and (ii) the Closing Sale Price of the Common Stock on June 29, 2024, in either case, subject to adjustment herein (the “Conversion Price”).

(3)

Conversion Shares Issuable Upon Conversion of Principal Amount; Delivery Date. The number of Conversion Shares issuable upon a conversion hereunder shall be determined by the quotient obtained by dividing (x) the outstanding principal amount of this Debenture to be converted plus accrued and unpaid interest thereon by (y) the Conversion Price. The Company shall deliver all Conversion Shares to the Holder within one (1) Trading Day after the date of the applicable Notice of Conversion (the “Conversion Share Delivery Date”).

The current outstanding principal balance of the Debentures as of April 16, 2024 is approximately $10.3 million and 5% exit fee is approximately $1.1m. If this Proposal 7 is approved, the current outstanding amount of the Debentures could be converted into common stock of the Company as set forth below, assuming a conversion price equal to the closing share price on April 16, 2024 of $1.65:

Common Stock Ownership after full conversion of Debentures
	Number of Common Stock Shares		% Ownership of Common Stock
Number of Shares issued to JGB		6,895,312		53%
Number of Shares held by all other Stockholders		6,046,560		47%

Common Stock Ownership after 50% conversion of Debentures
	Number of Common Stock Shares		% Ownership of Common Stock
Number of Shares issued to JGB		3,447,656		36%
Number of Shares held by all other Stockholders		6,046,560		64%

Reasons for Stockholder Approval

The JGB Amendment provides that the Company will use commercially reasonable efforts to obtain approval of the stockholders for the Voluntary Conversion Option.

Our common stock is listed on the Nasdaq Capital Market under the symbol “XXII,” and we are subject to the Nasdaq listing standards and rules. Under Rule 5635(b) of the Nasdaq Stock Market, stockholder approval is required prior to the issuance of securities when the issuance or potential issuance will result in a change of control of the Company. Section 5(b) of the Amended Debenture would result in a number of shares potentially being issued to effect a change of control of the Company, which would violate Rule 5635(b) without approval of our stockholders.

Under Rule 5635(d) of the Nasdaq Stock Market, stockholder approval is required in connection with a transaction, other than a public offering, at a price below the Minimum Price (as defined under Nasdaq rules) involving the sale, issuance or potential issuance by the Company of common stock (or securities convertible into or exercisable for common stock), which equals 20% or more of the common stock or 20% or more of the voting power outstanding before the issuance. Section 5(b) of the Amended Debenture would result in shares of common stock being potentially issued at a price below the Minimum Price and if this offering were combined with other offerings, it is possible that Section 5(b) of the Amended Debenture would violate Rule 5635(d) without approval of our stockholders.

Possible Effects of the Proposal

If the stockholders do not approve this Proposal 6, then the Voluntary Conversion Option will not be included in the Amended Debenture. However, the Company, as provided in the JGB Amendment will also be obligated to incur additional management resources and expenses to call and hold a meeting every in commercially reasonable increments thereafter to seek such stockholder approval until stockholder approval is obtained. Additionally, the failure to obtain stockholder approval may discourage future investors from engaging in

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future financings with us. If these consequences occur, we may have difficulty finding alternative sources of capital to fund our operations in the future on terms favorable to us or at all. We can provide no assurance that we would be successful in raising funds pursuant to additional equity or debt financings.

If the stockholders approve this Proposal 6, the Debentures will be convertible into shares of the Company’s common stock on the earlier of (i) June 30, 2024 and (ii) the public announcement of a Fundamental Transaction, which could result in substantial dilution to our stockholders and possibly a change in control of the Company.

Our Board of Directors recommends that the stockholders vote “FOR” Proposal 7 to
approve the Voluntary Conversion Option in the Debentures dated March 3, 2023 pursuant to Rules 5635(b) and (d) of the Nasdaq Stock Market.

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PROPOSAL NO. 8
THE RATIFICATION OF THE APPOINTMENT OF FREED MAXICK CPAs, P.C. AS
THE COMPANY’S INDEPENDENT REGISTERED CERTIFIED PUBLIC ACCOUNTING
FIRM FOR FISCAL YEAR 2024

The Audit Committee has appointed Freed Maxick CPAs, P.C. as our independent registered certified public accounting firm for the fiscal year 2024 and has further directed that the selection of Freed be submitted to a vote of stockholders at the Annual Meeting for ratification.

In selecting Freed to be our independent registered public accounting firm for 2024, our Audit Committee considered the results from its review of Freed’s independence, including (i) all relationships between Freed and our Company and any disclosed relationships or services that may impact Freed’s objectivity and independence; (ii) Freed’s performance and qualification as an independent registered public accounting firm; and (iii) the fact that the Freed engagement audit partner is rotated on a regular basis as required by applicable laws and regulations.

Our Audit Committee charter does not require that our stockholders ratify the selection of Freed as our independent registered public accounting firm. We are doing so because we believe it is a matter of good corporate governance practice. If our stockholders do not ratify the selection, our Audit Committee may reconsider whether to retain Freed, but still may retain the firm. Even if the selection is ratified, our Audit Committee, in its discretion, may change the appointment at any time during the year if it determines that such a change would be in the best interests of us and our stockholders.

Representatives of Freed are expected to attend the Annual Meeting, where they will be available to respond to appropriate questions and, if they desire, to make a statement.

The Audit Committee, in accordance with its charter, must pre-approve all non-audit services provided by our independent registered public accountants. The Audit Committee generally pre-approves specified series in the defined categories of audit services, audit related services and tax services up to specified amounts. Pre-approval may also be given as part of our Audit Committee’s approval of the scope of the engagement of the independent registered public accountants or on an individual, explicit case-by-case basis before the independent auditor is engaged to provide each service.

The Audit Committee has considered whether the provision of the services not related to the audit of the financial statements acknowledged in the table below was compatible with maintaining the independence of Freed and is of the opinion that the provision of these services was compatible with maintaining Freed’s independence.

The following table shows the fees billed to us for the audits and other services provided by for the fiscal years ended December 31, 2023 and 2022, respectively.

	2023			2022
Audit fees		$	570,000		$	430,100
Audit-related fees			—			—
Tax fees			—			—
All other fees			—			—
		$	570,000		$	430,100

Audit Fees consist of the aggregate fees billed for professional services rendered for the audit of our consolidated annual financial statements and the quarterly reviews of financial statements and for any other services that are normally provided by our independent registered public accountants in connection with our statutory and regulatory filings or engagements.

Our Board of Directors recommends that the stockholders vote “FOR” the proposal
to ratify the selection of Freed as our independent registered public accountants
for the year ending December 31, 2024.

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PROPOSAL NO. 9
THE ADJOURNMENT OF THE MEETING, IF NECESSARY OR ADVISABLE, TO SOLICIT ADDITIONAL PROXIES IN FAVOR OF PROPOSALS 1, 25, 6 OR 3.7

We are asking our stockholders to authorize us to adjourn the ~~Special~~Annual Meeting to another time and place, if necessary or advisable, to solicit additional proxies in the event there are not sufficient votes to approve ~~Proposals 1, 2~~the Charter Amendment (Proposal 1), the amendment and restatement of our 2021 Omnibus Incentive Plan (Proposal 5), to approve the Warrants (Proposal 6) or 3to approve the Voluntary Conversion Option (Proposal 7) described in this proxy statement at the ~~Special~~Annual Meeting. If our stockholders approve this proposal, we could adjourn the ~~Special~~Annual Meeting to solicit additional proxies and/or to seek to convince stockholders to change their votes in favor of such proposals.

If it is necessary or advisable to adjourn the ~~Special~~Annual Meeting, no notice of any adjournment of less than thirty (30) days is required to be given if the time and place of the adjourned meeting, and the means of remote communication, if any, by which stockholders and proxyholders may be deemed to be present in person and vote at such adjourned meeting, are announced at the meeting at which adjournment is taken, unless after the adjournment a new record date is fixed for the adjourned meeting. At the adjourned meeting, we may transact any business which might have been transacted at the original meeting.

Our Board of Directors recommends that the stockholders vote “FOR” ~~Proposal 4,~~ the adjournment of the meeting, if necessary or advisable, to solicit additional proxies in ~~the event there are not sufficient votes to approve~~favor of Proposals 1, 25, 6 or 3.7.

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BENEFICIAL OWNERSHIP

The following table sets forth information regarding the beneficial ownership of our common stock as of ~~December 6, 2023,~~April 16, 2024, by (i) each person who, to our knowledge, owns more than 5% of our common stock, (ii) each of our current directors, director nominees and ~~named~~ executive officers, and (iii) all our current directors, director nominees and executive officers as a group. To our knowledge, no person owns more than 5% of our common stock. Derivative securities exercisable or convertible into shares of our common stock within sixty (60) days of ~~December 6, 2023~~April 16, 2024 are deemed to be beneficially owned and outstanding for computing the share ownership and percentage of the person holding securities but are not deemed outstanding for computing the percentage of any other person. Beneficial ownership representing less than 1% is denoted with an asterisk (*). The address of named beneficial owners that are officers and/or directors of the Company is: c/o 22nd Century Group, Inc., ~~500 Seneca Street, Suite 507, Buffalo, New York 14204.~~321 Farmington Road, Mocksville, North Carolina. 27028. The following table is based upon information supplied by officers and directors, and with respect to 5% or greater stockholders who are not officers or directors, information filed with the SEC.

Name of Beneficial Owner

Number of
Shares
Beneficially
Owned

Percentage
Beneficially
Owned(1)

Number of
Shares
Beneficially
Owned

Percentage
Beneficially
Owned(1)

Management and Directors:

Lawrence D. Firestone

6,250

John Miller(2)

15,000

938

R. Hugh Kinsman(3)

3,489

601

James A. Mish(4)

52,894

Nora B. Sullivan(5) (6)

59,914

Andrew Arno

6,250

Richard M. Sanders~~(6)~~

29,623

2,387

Michael Koganov~~(6)~~

11,959

1,283

Anthony Johnson~~(6)~~

6,121

918

Lucille Salhany~~(6)~~

1,841

650

Peter Ferola(7)

—

Andrew Arno

—

Lawrence D. Firestone

—

All directors and executive officers as a group (11 persons) (2) –��(7)

180,841

0.4%

All directors and executive officers as a group (8 persons)(2) – (3)

19,277

0.3%

(1)

Based on ~~43,779,056~~6,046,560 shares of common stock issued and outstanding as of ~~December 6, 2023.~~

April 16, 2024.

(2)

Excludes ~~40,000~~2,500 performance shares vesting provided that the Company’s tobacco business plan revenue objectives and other performance requirements are satisfied at such times.

(3)

~~18,380~~766 restricted stock units are not included in the number of beneficially owned shares because they do not vest within 60 days of ~~December 6, 2023.~~

~~(4)~~

~~89,637 restricted stock units are not included in the number of beneficially owned shares because they do not vest within 60 days of December 6, 2023.~~

~~(5)~~

~~Consists of (a) 49,914 shares of common stock held directly and (b) 10,000 shares of common stock issuable upon exercise of stock options.~~

~~(6)~~

~~8,557 restricted stock units are not included in the number of beneficially owned shares because they do not vest within 60 days of December 6, 2023.~~

~~(7)~~

~~20,599 restricted stock units are not included in the number of beneficially owned shares because they do not vest within 60 days of December 6, 2023.~~April 16, 2024.

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RELATED PARTY TRANSACTIONS

Our policy is to enter into transactions with related persons on terms that, on the whole, are no less favorable to us than those available from unaffiliated third parties. Our Board of Directors has adopted written policies and procedures regarding related person transactions. For purposes of these policies and procedures:

•

A “related person” means any of our directors, executive officers, nominees for director, holder of 5% or more of our common stock or any of their immediate family members; and

•

A “related person transaction” generally is a transaction (including any indebtedness or a guarantee of indebtedness) in which we were or are to be a participant and the amount involved exceeds $120,000 and in which a related person had or will have a direct or indirect material interest.

Each of our executive officers, directors or nominees for director is required to disclose to our Audit Committee certain information relating to related person transactions for review, approval or ratification by our Audit Committee. In making a determination about approval or ratification of a related person transaction, our Audit Committee will consider the information provided regarding the related person transaction and whether consummation of the transaction is believed by the Audit Committee to be in our best interests. Our Audit Committee may take into account the effect of a director’s related person transaction on the director’s status as in independent member of our Board of Directors and eligibility to serve on committees of our Board under SEC rules and the listing standards of the Nasdaq Stock Market. Any related person transaction must be disclosed to our full Board of Directors. There were no related party transactions during 2023 and 2022.

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~~STOCKHOLDER PROPOSALS FOR THE 2024 ANNUAL MEETING OF STOCKHOLDERS AND COMMUNICATIONS WITH THE BOARD OF DIRECTORS~~Stockholder Proposals and Communications with the Board of Directors

Our amended and restated bylaws provide that, for matters to be properly brought before an Annual Meeting, business must be either (i) specified in the notice of Annual Meeting (or any supplement or amendment thereto) given by or at the direction of the Board of Directors, (ii) otherwise brought before the Annual Meeting by or at the direction of the Board of Directors, or (iii) otherwise properly brought before the Annual Meeting by a stockholder.

Stockholder proposals intended for inclusion in our proxy statement relating to the next Annual Meeting in ~~2024~~2025 must be received by us no later than December ~~27, 2023.~~30, 2024. Any such proposal must comply with Rule 14a 8 of Regulation 14A of the proxy rules of the SEC.

Notice to us of a stockholder proposal submitted otherwise than pursuant to Rule 14a 8 also will be considered untimely if received at our principal executive offices other than during the time period set forth below and will not be placed on the agenda for the meeting. In addition to any other applicable requirements, for business to be properly brought before an Annual Meeting by a stockholder, the stockholder must have given timely notice thereof in writing to our secretary. To be timely, a stockholder’s notice must be delivered to the secretary at our principal executive offices not later than the close of business on the ninetieth (90th) day nor earlier than the close of business on the one hundred twentieth (120th) day prior to the first anniversary of the preceding year’s Annual Meeting; provided, however, that in the event that the date of the Annual Meeting is more than thirty (30) days before or more than seventy (70) days after such anniversary date, notice by the stockholder must be so delivered not earlier than the close of business on the one hundred twentieth (120th) day prior to such Annual Meeting and not later than the close of business on the later of the ninetieth (90th) day prior to such Annual Meeting or the tenth (10th) day following the day on which public announcement of the date of such meeting is first made by us.

Stockholders may send communications to the Company’s directors as a group or individually, by writing to those individuals or the group: c/o the Chief Executive Officer of 22nd Century Group, Inc., ~~500 Seneca Street, Suite 507 Buffalo, New York 14204.~~321 Farmington Road, Mocksville, North Carolina 27028. The Chief Executive Officer will review all correspondence received and will forward all correspondence that is relevant to the duties and responsibilities of the Board or the business of the Company to the intended director(s). Examples of inappropriate communication include business solicitations, advertising and communication that are frivolous in nature, relates to routine business matters or raises grievances that are personal to the person submitting the communication. Upon request, any director may review communication that is not forwarded to the directors pursuant to this policy.

IMPORTANT NOTICE REGARDING THE INTERNET AVAILABILITY OF PROXY MATERIALS FOR THE ~~SPECIAL~~ANNUAL MEETING TO BE HELD ON ~~JANUARY 24,~~JUNE 28, 2024

This proxy statement and our ~~2022~~2023 Annual Report on Form 10-K for the fiscal year ended December 31, ~~2022,~~2023, as filed with the SEC, are available at www.xxiicentury.com/investors/sec-filings. For directions to the ~~Special~~Annual Meeting, please contact Matt Kreps at (716) 270-1523 or through www.xxiicentury.com/contact.

OTHER MATTERS

The Board knows of no matter to be brought before the ~~Special~~Annual Meeting other than the matters identified in this proxy statement. However, if any other matter properly comes before the ~~Special~~Annual Meeting or any adjournment of the meeting, it is the intention of the persons named in the proxy solicited by the Board to vote the shares represented by them in accordance with their best judgment.

* * * * * * * * *

The reports of the Audit Committee and the Compensation Committee included elsewhere in this proxy statement do not constitute soliciting materials and should not be deemed filed or incorporated by reference into any other filing made by us under the Securities Act of 1933 or the Securities Exchange Act of 1934, except to the extent that we specifically incorporate these reports by reference in another filing.

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~~APPENDIX~~Appendix A

CERTIFICATE OF AMENDMENT TO ARTICLES OF INCORPORATION TO ELIMINATE
~~(Reverse Split)~~CLASSIFIED BOARD STRUCTURE

~~Pursuant to~~1.

Article 5 is hereby deleted in its entirety and replaced with the ~~requirements~~following:

ARTICLE V
DIRECTORS

The business and affairs of ~~NRS 78.2055,~~the Corporation shall be managed by or under the direction of the board of directors, which shall consist of ~~22nd Century Group, Inc. (the “Corporation”) proposed and recommended to~~at least one director. Provided that the ~~stockholders a recommendation to decrease, on a 1-for-[ ] basis,~~Corporation has at least one director, the number of ~~issued and outstanding shares of Common Stock, $0.00001 par value per share, of the Corporation, without~~directors may at any ~~adjustment to the par value per share and without any reduction~~time or times be increased or decreased as provided in the authorized number of shares of Common Stock, and the proposal was approved by the stockholders holding shares in the Corporation entitling them to exercise at least a majority of the voting power, or such greater proportion of the voting power as may be required in the case of a vote by classes or series, or as is otherwise required by the provisions of the Articles of Incorporation.

~~ARTICLE IV~~
~~CAPITAL STOCK~~

~~The Restated Articles of Incorporation are hereby amended by adding the following as a new paragraph to the end of section 4.1:~~

“Upon the effectiveness of the filing (the “Effective Time”) of the Amendment of Restated Articles of Incorporation pursuant to the Chapter 78 of the NRS, each [ ] shares of the Corporation’s Common Stock issued and outstanding immediately prior to the Effective Time shall be reclassified and combined into one (1) validly issued, fully paid and non-assessable share of the Corporation’s Common Stock automatically and without any further action by the Corporation or the holder thereof, subject to the treatment of fractional share interests as described below (the “Reverse Stock Split”). The Corporation shall not issue to any holder a fractional share of Common Stock on account of the Reverse Stock Split. [Rather, any fractional share of Common Stock resulting from such change shall be rounded upward to the nearest whole share of Common Stock. Share interests issued due to rounding are given solely to save the expense and inconvenience of issuing fractional shares of Common Stock and do not represent separately bargained for consideration.][The Corporation shall, in lieu of such fractional share, pay to the holder a sum in cash equal to such fraction multiplied by the closing sales price of the Common Stock as reported on the Nasdaq Capital Market on the last trading day before the Effective Time (as adjusted to give effect to the Reverse Stock Split).] Until surrendered, each certificatebylaws; provided, however that ~~immediately prior to the Effective Time represented shares of Common Stock (“Old Certificates”) shall only represent~~ the number of ~~whole shares~~directors shall not exceed ten. Directors shall be elected at every annual meeting of ~~Common Stock into which the shares of Common Stock formerly represented by such Old Certificate were combined into as a result of the Reverse Stock Split.”~~stockholders to one-year terms.

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~~APPENDIX~~Appendix B

~~CERTIFICATE OF AMENDMENT~~22nd CENTURY GROUP, INC.
~~(Increase~~2021 OMNIBUS INCENTIVE PLAN
As Amended and Restated

Purpose, Effective Date, Amendment and Restatement, Effect on Prior Plan and Definitions.

(a) Purpose. This 22nd Century Group, Inc. 2021 Omnibus Incentive Plan, as amended and restated, has two complementary purposes: (i) to attract, retain, focus and motivate executives and other selected employees, directors, consultants and advisors and (ii) to increase stockholder value. The Plan will accomplish these objectives by offering participants the opportunity to acquire shares of the Company’s common stock, receive monetary payments based on the value of such common stock or receive other incentive compensation on the terms that this Plan provides.

(b) Effective Date; Amendment and Restatement. This Plan became effective as of May 20, 2021, the date on which the Plan was approved by the Company’s stockholders (the “Effective Date”). The Board amended and restated this Plan on March 7, 2023, and the stockholders voted to approve the plan as amended on June 16, 2023. The Board further amended and restated this Plan on April 19, 2024, contingent on subsequent stockholder approval of this Plan as amended and restated.

(c) Effect on Prior Plan. Upon the Effective Date, the 22nd Century Group, Inc. 2014 Omnibus Incentive, as amended and restated (the “Prior Plan”) terminated, and no new awards could be granted thereunder after the Effective Date, although awards previously granted under the Prior Plan and still outstanding, continue to be subject to all terms and conditions of the Prior Plan.

(d) Definitions. Capitalized terms used and not otherwise defined in ~~Authorized Shares)~~various sections of the Plan have the meanings given in Section 18.

~~(attached)~~2. Administration.

(a) Administration. In addition to the authority specifically granted to the Administrator in this Plan, the Administrator has full discretionary authority to administer this Plan and all Awards, including but not limited to the authority to: (i) interpret the provisions of this Plan and any Award Agreement; (ii) prescribe, amend and rescind rules and regulations relating to this Plan; (iii) correct any defect, supply any omission, or reconcile any inconsistency in the Plan, any Award or any agreement covering an Award in the manner and to the extent it deems desirable to carry this Plan or such Award into effect; and (iv) make all other determinations necessary or advisable for the administration of this Plan. All Administrator determinations shall be made in the sole discretion of the Administrator and are final and binding on all interested parties.

Notwithstanding any provision of the Plan to the contrary, the Administrator shall have the discretion to grant an Award with any vesting condition, any vesting period or any performance period if the Award is granted to a newly hired or promoted Participant, or accelerate or shorten the vesting or performance period of an Award, in connection with a Participant’s death, Disability, retirement or termination by the Company or an Affiliate without Cause or a Change of Control.

(b) Delegation to Other Committees or Officers. To the extent applicable law permits, the Board may delegate to another committee of the Board or to one or more officers of the Company, or the Committee may delegate to one or more officers of the Company, any or all of their respective authority and responsibility as an Administrator of the Plan; provided that no such delegation is permitted with respect to Stock-based Awards made to Section 16 Participants at the time any such delegated authority or responsibility is exercised unless the delegation is to another committee of the Board consisting entirely of Non-Employee Directors. If the Board or the Committee has made such a delegation, then all references to the Administrator in this Plan include such other committee or one or more officers to the extent of such delegation.

(c) No Liability; Indemnification. No member of the Board or the Committee, and no officer or member of any other committee to whom a delegation under Section 2(b) has been made, will be liable

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for any act done, or determination made, by the individual in good faith with respect to the Plan or any Award. The Company will indemnify and hold harmless each such individual as to any acts or omissions, or determinations made, with respect to this Plan or any Award to the maximum extent that the law and the Company’s by-laws permit.

3. Eligibility. The Administrator may designate any of the following as a Participant from time to time, to the extent of the Administrator’s authority: any officer or other employee of the Company or its Affiliates; any individual that the Company or an Affiliate has engaged to become an officer or employee; any consultant or advisor who provides services to the Company or its Affiliates; or any Director, including a Non-Employee Director. The Administrator’s granting of an Award to a Participant will not require the Administrator to grant an Award to such individual at any future time. The Administrator’s granting of a particular type of Award to a Participant will not require the Administrator to grant any other type of Award to such individual.

4. Types of Awards. Subject to the terms of this Plan, the Administrator may grant any type of Award to any Participant it selects, but only employees of the Company or a Subsidiary (that qualifies under Code Section 422) may receive grants of incentive stock options within the meaning of Code Section 422. Awards may be granted alone or in addition to, in tandem with, or (subject to the prohibition on repricing set forth in Section 14(e)) in substitution for any other Award (or any other award granted under another plan of the Company or any Affiliate, including the plan of an acquired entity).

5. Shares Reserved under this Plan.

(a) Plan Reserve. Subject to adjustment as provided in Section 16, an aggregate of 5,566,667 Shares, plus the number of Shares available for issuance under the Prior Plan that had not been made subject to outstanding awards as of the Effective Date, plus the number of Shares described in Section 5(c), are reserved for issuance under this Plan. The Shares reserved for issuance may be either authorized and unissued Shares or Shares reacquired at any time and now or hereafter held as treasury stock. The aggregate number of Shares reserved under this Section 5(a) shall be depleted by the maximum number of Shares, if any, that may be issuable under an Award as determined at the time of grant. Notwithstanding the foregoing, no more than 5,566,667 Shares may be issued upon the exercise of incentive stock options. For purposes of determining the aggregate number of Shares reserved for issuance under this Plan, any fractional Share shall be rounded to the next highest full Share.

(b) Replenishment of Shares Under this Plan. If (i) an Award lapses, expires, terminates or is cancelled without the issuance of Shares under the Award (whether due currently or on a deferred basis) or is settled in cash, (ii) it is determined during or at the conclusion of the term of an Award that all or some portion of the Shares with respect to which the Award was granted will not be issuable on the basis that the conditions for such issuance will not be satisfied, (iii) Shares are forfeited under an Award or (iv) Shares are issued under any Award and the Company subsequently reacquires them pursuant to rights reserved upon the issuance of the Shares, then such Shares shall be recredited to the Plan’s reserve and may again be used for new Awards under this Plan, but Shares recredited to the Plan’s reserve pursuant to clause (iv) may not be issued pursuant to incentive stock options. Notwithstanding the foregoing, in no event shall the following Shares be recredited to this Plan’s reserve: Shares tendered in payment of or withheld to satisfy the exercise price of an Option or as a result of the net settlement of an outstanding Stock Appreciation Right (subject to compliance with applicable law); Shares withheld to satisfy federal, state or local tax withholding obligations (including in connection with the exercise or net settlement of an outstanding Stock Appreciation Right); and Shares purchased by the Company (subject to compliance with applicable law) using proceeds from Option exercises.

(c) Addition of Shares from Prior Plan. After the Effective Date, if any Shares subject to awards granted under the Prior Plan would become available to be re-credited to the Prior Plan’s reserve if such plan was still in effect (but applying the provisions of subsection (b) above and the Prior Plan’s limits on re-crediting), then those Shares will be available for the purpose of granting Awards under this Plan, thereby increasing the reserve.

(d) Award Limit. Subject to adjustment as provided in Section 16, the maximum number of Shares that may be subject to Awards granted during any fiscal year to any individual Non-Employee Director shall not exceed that number of Shares that equates to a grant date fair value of, when added to any cash

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compensation received by such Non-Employee Director, $600,000 (the “Director Limit”); provided that the Board may make exceptions to the Director Limit in extraordinary circumstances as the Board may determine in its discretion; provided further that the Non-Employee Director receiving such additional compensation may not participate in the decision to award such compensation.

6. Options. Subject to the terms of this Plan, the Administrator will determine all terms and conditions of each Option, including but not limited to: (a) whether the Option is an “incentive stock option” which meets the requirements of Code Section 422, or a “nonqualified stock option” which does not meet the requirements of Code Section 422; (b) the grant date, which may not be any day prior to the date that the Administrator approves the grant; (c) the number of Shares subject to the Option; (d) the exercise price, which may not be less than the Fair Market Value of the Shares subject to the Option as determined on the date of grant (other than in the case of an Option that is not an incentive stock option and that complies with Code Section 409A); (e) the terms and conditions of vesting and exercise; and (f) the term, except that an Option must terminate no later than ten (10) years after the date of grant. In all other respects, the terms of any incentive stock option should comply with the provisions of Code Section 422 except to the extent the Administrator determines otherwise. Except to the extent the Administrator determines otherwise, a Participant may exercise an Option in whole or part after the right to exercise the Option has accrued, provided that any partial exercise must be for one hundred (100) Shares or multiples thereof. If an Option that is intended to be an incentive stock option fails to meet the requirements thereof, the Option shall automatically be treated as a nonqualified stock option to the extent of such failure. Unless restricted by the Administrator, and subject to such procedures as the Administrator may specify, the payment of the exercise price of Options made be made by (w) delivery of cash or other Shares or other securities of the Company (including by attestation) having a then Fair Market Value equal to the purchase price of such Shares, (x) by delivery (including by fax) to the Company or its designated agent of an executed irrevocable option exercise form together with irrevocable instructions to a broker-dealer to sell or margin a sufficient portion of the Shares and deliver the sale or margin loan proceeds directly to the Company to pay for the exercise price, (y) by surrendering the right to receive Shares otherwise deliverable to the Participant upon exercise of the Award having a Fair Market Value at the time of exercise equal to the total exercise price, or (z) by any combination of (w), (x) and/or (y). Except to the extent otherwise set forth in an Award agreement, a Participant shall have no rights as a holder of Stock as a result of the grant of an Option until the Option is exercised, the exercise price and applicable withholding taxes are paid and the Shares subject to the Option are issued thereunder.

7. Stock Appreciation Rights. Subject to the terms of this Plan, the Administrator will determine all terms and conditions of each SAR, including but not limited to: (a) whether the SAR is granted independently of an Option or relates to an Option; (b) the grant date, which may not be any day prior to the date that the Administrator approves the grant; (c) the number of Shares to which the SAR relates; (d) the grant price, provided that the grant price shall not be less than the Fair Market Value of the Shares subject to the SAR as determined on the date of grant (unless such SAR complies with Code Section 409A); (e) the terms and conditions of exercise or maturity, including vesting; (f) the term, provided that an SAR must terminate no later than ten (10) years after the date of grant; and (g) whether the SAR will be settled in cash, Shares or a combination thereof. If an SAR is granted in relation to an Option, then unless otherwise determined by the Administrator, the SAR shall be exercisable or shall mature at the same time or times, on the same conditions and to the extent and in the proportion, that the related Option is exercisable and may be exercised or mature for all or part of the Shares subject to the related Option. Upon exercise of any number of SARs, the number of Shares subject to the related Option shall be reduced accordingly and such Option may not be exercised with respect to that number of Shares. The exercise of any number of Options that relate to an SAR shall likewise result in an equivalent reduction in the number of Shares covered by the related SAR.

8. Performance and Stock Awards. Subject to the terms of this Plan, the Administrator will determine all terms and conditions of each award of Shares, Restricted Stock, Restricted Stock Units, Performance Shares or Performance Units, including but not limited to: (a) the number of Shares and/or units to which such Award relates; (b) whether, as a condition for the Participant to realize all or a portion of the benefit provided under the Award, one or more Performance Goals must be achieved during such period as the Administrator specifies; (c) whether the restrictions imposed on Restricted Stock or Restricted Stock Units shall lapse, and all or a portion of the Performance Goals subject to an Award shall be deemed achieved, upon a Participant’s death, Disability or retirement; (d) the length of the vesting and/or performance period and, if different, the date on which payment of the benefit provided under the Award will be made; (e) with respect to Performance

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Units, whether to measure the value of each unit in relation to a designated dollar value or the Fair Market Value of one or more Shares; and (f) with respect to Restricted Stock Units and Performance Units, whether to settle such Awards in cash, in Shares (including Restricted Stock), or a combination thereof.

BROADRIDGE CORPORATE ISSUER SOLUTIONS C/O 22ND CENTURY GROUP, INC. P.O.BOX 1342 BRENTWOOD, NY 11717 Investor Address Line 1 Investor Address Line 2 Investor Address Line 3 Investor Address Line 4 Investor Address Line 5 John Sample 1234 ANYWHERE STREET ANY CITY, ON A1A 1A1 234567 SCAN TO VIEW MATERIALS & VOTE VOTE BY INTERNET - www.proxyvote.com9. Annual Incentive Awards. Subject to the terms of this Plan, the Administrator will determine all terms and conditions of an Annual Incentive Award, including but not limited to the Performance Goals, performance period, the potential amount payable, and the timing of payment; provided that the Administrator must require that payment of all or ~~scan~~any portion of the ~~QR Barcode above Use~~amount subject to the ~~Internet~~Annual Incentive Award is contingent on the achievement of one or more Performance Goals during the period the Administrator specifies, although the Administrator may specify that all or a portion of the Performance Goals subject to ~~transmit your voting instructions~~an Award are deemed achieved upon a Participant’s death, Disability or retirement, or such other circumstances as the Administrator may specify.

10. Long-Term Incentive Awards. Subject to the terms of this Plan, the Administrator will determine all terms and conditions of a Long-Term Incentive Award, including but not limited to the Performance Goals, performance period (which must be more than one year), the potential amount payable, and the timing of payment; provided that the Administrator must require that payment of all or any portion of the amount subject to the Long-Term Incentive Award is contingent on the achievement of one or more Performance Goals during the period the Administrator specifies, although the Administrator may specify that all or a portion of the Performance Goals subject to an Award are deemed achieved upon a Participant’s death, Disability or retirement, or such other circumstances as the Administrator may specify.

11. Dividend Equivalent Units; Dividends.

(a) Prohibitions. In no event may dividends or Dividend Equivalent Units be awarded with respect to Options, Stock Appreciation Rights or any other stock-based award that is not a grant of Performance Shares, Performance Units, Restricted Stock, Restricted Stock Units or Shares. Notwithstanding anything to the contrary in this Plan, and for ~~electronic delivery~~the avoidance of ~~information. Vote by 11:59 P.M. ET~~doubt, this Plan expressly prohibits the payment of dividends or Dividend Equivalent Units on ~~01/24/2024. Have your proxy card~~unvested Awards for all equity Award types.

(b) Dividends. If cash dividends are paid while shares of Restricted Stock are unvested, then such dividends will either, at the discretion of the Administrator, be (i) automatically reinvested as additional shares of Restricted Stock that are subject to the same terms and conditions, including the risk of forfeiture, as the original grant of Restricted Stock, or (ii) paid in ~~hand when you access~~cash at the ~~web site~~same time and ~~follow~~ the ~~instructions~~same extent that the Restricted Stock vests. For clarity, in no event will dividends be distributed to ~~obtain your records~~a Participant unless, until and to ~~create~~the same extent as the underlying shares of Restricted Stock vest.

(c) Dividend Equivalent Units. The Administrator may grant Dividend Equivalent Units only in tandem with Restricted Stock Units, Performance Shares or Performance Units. Dividend Equivalent Units will either, at the discretion of the Administrator, be (i) accumulated and paid, in cash or Shares in the Administrator’s discretion, at the same time and to the same extent that the tandem Award vests or is earned or (ii) reinvested in additional units that are subject to the same terms and conditions (including vesting and forfeiture) as the tandem Award. The Administrator will determine all other terms and conditions of each award of Dividend Equivalent Units. For clarity, in no event will a Participant receive payment with respect to a Dividend Equivalent Unit unless, until and to the same extent as the tandem Award vests and is paid.

12. Other Stock-Based Awards. Subject to the terms of this Plan, the Administrator may grant to Participants other types of Awards, which may be denominated or payable in, valued in whole or in part by reference to, or otherwise based on, Shares, either alone or in addition to or in conjunction with other Awards, and payable in Stock or cash. Without limitation except as provided herein (and subject to the limitations of Section 14(e)), such Award may include the issuance of shares of unrestricted Stock, which may be awarded in payment of director fees, in lieu of cash compensation, in exchange for cancellation of a compensation right, as a bonus, or upon the attainment of Performance Goals or otherwise, or rights to acquire Stock from the Company. The Administrator shall determine all terms and conditions of the Award, including but not limited to, the time or times at which such Awards shall be made, and the number of Shares to be granted pursuant to such Awards or to which such Award shall relate; provided that any Award that provides for purchase rights shall be priced at 100% of Fair Market Value on the date of the Award.

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13. Minimum Vesting Period; Discretion to Acceleration Vesting; Restrictions on Transfer, Encumbrance and Disposition.

(a) Minimum Vesting Period. All Awards granted under the Plan that may be settled in Shares must have a minimum vesting period of one (1) year from the date of grant, provided that such minimum vesting period will not apply to Awards with respect to up to five percent (5%) of the total number of Shares reserved pursuant to Section 5. For purposes of Awards granted to Non-Employee Directors, “one year” may mean the period of time from one annual stockholders meeting to the next annual stockholders meeting, provided that such period of time is not less than fifty (50) weeks.

(b) Discretion to Accelerate. Notwithstanding Section 13(a), the Administrator may accelerate the vesting of an ~~electronic voting instruction form. ELECTRONIC DELIVERY~~Award or deem an Award to be earned, in whole or in part, in the event of (i) a Participant’s death, disability, retirement, or termination without Cause, (ii) as provided in Section 16(c) or (iii) upon any other event as determined by the Administrator in its sole and absolute discretion.

(c) Restrictions on Transfer, Encumbrance and Disposition. No Award granted under this Plan may be sold, assigned, mortgaged, pledged, exchanged, hypothecated or otherwise transferred, or encumbered or disposed of, by a Participant other than by will or the laws of descent and distribution, and during the lifetime of the Participant such Awards may be exercised only by the Participant or the Participant’s legal representative or by the permitted transferee of such Participant as hereinafter provided (or by the legal representative of such permitted transferee). Notwithstanding the foregoing, a Participant may transfer an Award if permitted by the Administrator. Subsequent transfers of transferred Awards are prohibited except transfers otherwise made in accordance with this Section 13(c). Any attempted transfer not permitted by this Section 13(c) shall be null and void and have no legal effect. The restrictions set forth in this Section 13(c), and any risk of forfeiture applicable to an Award, shall be enforceable against any transferee of an Award.

14. Termination and Amendment of Plan; Amendment, Modification or Cancellation of Awards.

(a) Term of Plan. Unless the Board earlier terminates this Plan pursuant to Section 14(b), this Plan will terminate on the tenth (10th) anniversary of the most recent shareholder approval. For the avoidance of doubt, shareholder approval for the purposes of this section includes shareholder approval to amend and restate the Plan.

(b) Termination and Amendment. The Board or the Administrator may amend, alter, suspend, discontinue or terminate this Plan at any time, subject to the following limitations:

(i) the Board must approve any amendment of this Plan to the extent the Company determines such approval is required by: (A) prior action of the Board, (B) applicable corporate law, or (C) any other applicable law;

(ii) stockholders must approve any amendment of this Plan to the extent the Company determines such approval is required by: (A) Section 16 of the Exchange Act, (B) the Code, (C) the listing requirements of any principal securities exchange or market on which the Shares are then traded, or (D) any other applicable law; and

(iii) stockholders must approve any of the following Plan amendments: (A) an amendment to materially increase any number of Shares specified in Section 5(except as permitted by Section 16), (B) an amendment that would materially expand the group of individuals that may become Participants, or (C) an amendment that would diminish the protections afforded by Section 14(e).

If the Administrator takes any action under this Plan that is not, at the time of such action, authorized by this Plan, but that could be authorized by this Plan as amended by the Administrator, the Administrator action will be deemed to constitute an amendment to this Plan to authorize such action to the extent permissible under applicable law and the requirements of any principal securities exchange or market on which the Shares are then traded

(i) Except as provided in Section 14(e) and subject to the requirements of this Plan, the Administrator may modify, amend or cancel any Award, or waive any restrictions or conditions

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applicable to any Award or the exercise of the Award; provided that, except as otherwise provided in the Plan or the Award agreement, any modification or amendment that materially diminishes the rights of the Participant, or the cancellation of the Award, shall be effective only if agreed to by the Participant or any other person(s) as may then have an interest in the Award, but the Administrator need not obtain Participant (or other interested party) consent for the modification, amendment or cancellation of an Award pursuant to the provisions of subsection (ii) or Section 16 or as follows: (A) to the extent the Administrator deems such action necessary to comply with any applicable law or the listing requirements of any principal securities exchange or market on which the Shares are then traded; (B) to the extent the Administrator deems necessary to preserve favorable accounting or tax treatment of any Award for the Company; or (C) to the extent the Administrator determines that such action does not materially and adversely affect the value of an Award or that such action is in the best interest of the affected Participant (or any other person(s) as may then have an interest in the Award). Notwithstanding the foregoing, unless determined otherwise by the Administrator, any such amendment shall be made in a manner that will enable an Award intended to be exempt from Code Section 409A to continue to be so exempt, or to enable an Award intended to comply with Code Section 409A to continue to so comply.

(ii) Notwithstanding anything to the contrary in an Award agreement, the Administrator shall have full power and authority to terminate or cause the Participant to forfeit the Award, and require the Participant to disgorge to the Company any gains attributable to the Award, if the Participant engages in any action constituting, as determined by the Administrator in its discretion, Cause for termination, or a breach of any Award agreement or any other agreement between the Participant and the Company or an Affiliate concerning noncompetition, nonsolicitation, confidentiality, trade secrets, intellectual property, nondisparagement or similar obligations.

(iii) Any Awards granted pursuant to this Plan, and any Stock issued, or cash paid pursuant to an Award, shall be subject to any recoupment or clawback policy that is adopted by, or any recoupment or similar requirement otherwise made applicable by law, regulation or listing standards to, the Company from time to time.

(d) Survival of Authority and Awards. Notwithstanding the foregoing, the authority of the Board and the Administrator under this Section 14 and to otherwise administer the Plan with respect to then-outstanding Awards will extend beyond the date of this Plan’s termination. In addition, termination of this Plan will not affect the rights of Participants with respect to Awards previously granted to them, and all unexpired Awards will continue in force and effect after termination of this Plan except as they may lapse or be terminated by their own terms and conditions.

(e) Repricing and Backdating Prohibited. Notwithstanding anything in this Plan to the contrary, and except for the adjustments provided for in Section 16, neither the Administrator nor any other person may (i) amend the terms of outstanding Options or SARs to reduce the ~~costs incurred~~exercise or grant price of such outstanding Options or SARs; (ii) cancel outstanding Options or SARs in exchange for Options or SARs with an exercise or grant price that is less than the exercise or grant price of the original Options or SARs; or (iii) cancel outstanding Options or SARs with an exercise or grant price above the current Fair Market Value of a Share in exchange for cash or other securities. In addition, the Administrator may not make a grant of an Option or SAR with a grant date that is effective prior to the date the Administrator takes action to approve such Award.

(f) Foreign Participation. To assure the viability of Awards granted to Participants employed or residing in foreign countries, the Administrator may provide for such special terms as it may consider necessary or appropriate to accommodate differences in local law, tax policy, accounting or custom. Moreover, the Administrator may approve such supplements to, or amendments, restatements or alternative versions of, this Plan as it determines is necessary or appropriate for such purposes. Any such amendment, restatement or alternative versions that the Administrator approves for purposes of using this Plan in a foreign country will not affect the terms of this Plan for any other country. In addition, all such supplements, amendments, restatements or alternative versions must comply with the provisions of Section 14(b)(ii).

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(g) Code Section 409A. The provisions of Code Section 409A are incorporated herein by ~~our company~~reference to the extent necessary for any Award that is subject to Code Section 409A to comply therewith.

15. Taxes.

(a) Withholding. In the event the Company or one of its Affiliates is required to withhold any Federal, state or local taxes or other amounts in ~~mailing proxy materials, you can~~respect of any income recognized by a Participant as a result of the grant, vesting, payment, settlement of, or other event with respect to, an Award or disposition of any Shares acquired under an Award, the Company or its Affiliate may deduct (or require an Affiliate to deduct) from any cash payments of any kind otherwise due the Participant, or with the consent of the Administrator, Shares otherwise deliverable or vesting under an Award, to ~~receiving~~satisfy such tax or other obligations. Alternatively, the Company or its Affiliate may require such Participant to pay to the Company or its Affiliate, in cash, promptly on demand, or make other arrangements satisfactory to the Company or its Affiliate regarding the payment to the Company or its Affiliate of the aggregate amount of any such taxes and other amounts. If Shares are deliverable upon exercise or payment of an Award, then, unless restricted by the Administrator and subject to such procedures as the Administrator may specify, a Participant may satisfy all ~~future proxy statements, proxy cards~~or a portion of the Federal, state and ~~special reports electronically via e-mail~~local withholding tax obligations arising in connection with such Award by electing to (i) have the Company or its Affiliate withhold Shares otherwise issuable under the Award, (ii) tender back Shares received in connection with such Award or (iii) deliver other previously owned Shares; provided that the amount to be withheld in Shares may not exceed the total maximum statutory tax rates associated with the transaction to the extent needed for the Company and its Affiliates to avoid an accounting charge. If an election is provided, the election must be made on or before the date as of which the amount of tax to be withheld is determined and otherwise as the Administrator requires. In any case, the Company and its Affiliates may defer making payment or delivery under any Award if any such tax may be pending unless and until indemnified to its satisfaction.

(b) No Guarantee of Tax Treatment. Notwithstanding any provisions of the Plan, the Company does not guarantee to any Participant or any other Person with an interest in an Award that (i) any Award intended to be exempt from Code Section 409A shall be so exempt, (ii) any Award intended to comply with Code Section 409A or Code Section 422 shall so comply, or (iii) any Award shall otherwise receive a specific tax treatment under any other applicable tax law, nor in any such case will the Company or any Affiliate be required to indemnify, defend or hold harmless any individual with respect to the tax consequences of any Award.

(c) Participant Responsibilities. If a Participant shall dispose of Shares acquired through exercise of an incentive stock option within either (i) two (2) years after the date the Option is granted or (ii) one (1) year after the date the Option is exercised (i.e., in a disqualifying disposition), such Participant shall notify the Company within seven (7) days of the date of such disqualifying disposition. In addition, if a Participant elects, under Code Section 83, to be taxed at the time an Award of Restricted Stock (or other property subject to such Code section) is made, rather than at the time the Award vests, such Participant shall notify the Company within seven (7) days of the date the Participant makes such an election.

16. Adjustment Provisions; Change of Control.

(a) Adjustment of Shares. If: (i) the Company shall at any time be involved in a merger or other transaction in which the Shares are changed or exchanged; (ii) the Company shall subdivide or combine the Shares or the ~~Internet.~~Company shall declare a dividend payable in Shares, other securities (other than stock purchase rights issued pursuant to a stockholder rights agreement) or other property; (iii) the Company shall effect a cash dividend the amount of which, on a per Share basis, exceeds ten percent (10%) of the Fair Market Value of a Share at the time the dividend is declared, or the Company shall effect any other dividend or other distribution on the Shares in the form of cash, or a repurchase of Shares, that the Board determines by resolution is special or extraordinary in nature or that is in connection with a transaction that the Company characterizes publicly as a recapitalization or reorganization involving the Shares; or (iv) any other event shall occur, which, in the case of this clause (iv), in the judgment of the Administrator necessitates an adjustment to prevent dilution or enlargement of the benefits or potential benefits intended to be made available under this Plan, then the Administrator shall, in such manner as it may deem equitable to prevent dilution or enlargement of the benefits or potential benefits intended to

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be made available under this Plan, adjust as applicable: (A) the number and type of Shares subject to this Plan (including the number and type of Shares described in Section 5) and which may after the event be made the subject of Awards; (B) the number and type of Shares subject to outstanding Awards; (C) the grant, purchase, or exercise price with respect to any Award; and (D) the Performance Goals of an Award. However, in each case, with respect to Awards of incentive stock options, no such adjustment may be authorized to the extent that such authority would cause this Plan to violate Code Section 422(b). Further, the number of Shares subject to any Award payable or denominated in Shares must always be a whole number. In any event, previously granted Options or SARs are subject to only such adjustments as are necessary to maintain the relative proportionate interest the Options and SARs represented immediately prior to any such event and to preserve, without exceeding, the value of such Options or SARs.

Without limitation, in the event of any reorganization, merger, consolidation, combination or other similar corporate transaction or event, whether or not constituting a Change of Control (other than any such transaction in which the Company is the continuing corporation and in which the outstanding Stock is not being converted into or exchanged for different securities, cash or other property, or any combination thereof), the Administrator may substitute, on an equitable basis as the Administrator determines, for each Share then subject to an Award and the Shares subject to this Plan (if the Plan will continue in effect), the number and kind of shares of stock, other securities, cash or other property to which holders of Stock are or will be entitled in respect of each Share pursuant to the transaction.

Notwithstanding the foregoing, in the case of a stock dividend (other than a stock dividend declared in lieu of an ordinary cash dividend) or subdivision or combination of the Shares (including a reverse stock split), if no action is taken by the Administrator, adjustments contemplated by this subsection that are proportionate shall nevertheless automatically be made as of the date of such stock dividend or subdivision or combination of the Shares.

For the avoidance of doubt, the grant of an Award shall not affect in any way the right or power of the Company or any of its Affiliates to make or authorize any or all adjustments, recapitalizations, reorganizations or other changes in the Company’s or such Affiliate’s capital structure or business, or any merger, consolidation or business combination of the Company or such Affiliate, or any issuance or modification of any term, condition, or covenant of any bond, debenture, debt, preferred stock or other instrument ahead of or affecting the Stock or the rights of the holders of Stock, or the dissolution or liquidation of the Company or any Affiliate, or any sale or transfer of all or any part of its assets or business or any other Company or Affiliate action or proceeding, whether of a similar character or otherwise.

(b) Issuance or Assumption. Notwithstanding any other provision of this Plan, and without affecting the number of Shares otherwise reserved or available under this Plan, in connection with any merger, consolidation, acquisition of property or stock, or reorganization, the Administrator may authorize the issuance or assumption of awards under this Plan upon such terms and conditions as it may deem appropriate.

(c) Change of Control. To ~~sign up~~the extent a Participant has in effect an employment, retention, change of control, severance or similar agreement with the Company or any Affiliate that discusses the effect of a Change of Control on the Participant’s Awards, such agreement shall control. In all other cases, unless provided otherwise in an Award agreement or by the Administrator prior to the date of the Change of Control, in the event of a Change of Control:

(i) If the purchaser, successor or surviving entity (or parent thereof) so agrees, some or all outstanding Awards shall be assumed, or replaced with the same type of award with similar terms and conditions, by the purchaser, successor or surviving entity (or parent thereof) in the Change of Control transaction that is consummated. If applicable, each Award which is assumed by the purchaser, successor or surviving entity (or parent thereof) shall be appropriately adjusted, immediately after such Change of Control, to apply to the number and class of securities which would have been issuable to the Participant upon the consummation of such Change of Control had the Award been exercised, vested or earned immediately prior to such Change of Control, and other appropriate adjustments in the terms and conditions of the Award shall be made. Upon the Participant’s termination of employment by the successor or surviving entity without Cause, or by

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the Participant for ~~electronic~~Good Reason, in either case within twenty-four (24) months following the Change of Control, all of the Participant’s Awards that are in effect as of the date of such termination shall be vested in full or deemed earned in full (assuming the maximum performance goals provided under such Award were met, if applicable) effective on the date of such termination.

(ii) To the extent the purchaser, successor or surviving entity (or parent thereof) in the Change of Control transaction that is consummated does not assume the Awards or issue replacement awards as provided in clause (i), then immediately prior to the date of the Change of Control:

(A) Each Option or SAR that is then held by a Participant who is employed by or in the service of the Company or an Affiliate shall become immediately and fully vested, and, unless otherwise determined by the Board or Committee, all Options and SARs shall be cancelled on the date of the Change of Control in exchange for a cash payment equal to the excess of the Change of Control price of the Shares covered by the Option or SAR that is so cancelled over the purchase or grant price of such Shares under the Award (for no payment, if there is no such excess);

(B) Restricted Stock, Restricted Stock Units and Shares that are not then vested shall vest;

(C) all Performance Shares and/or Performance Units that are earned but not yet paid shall be paid in cash in an amount equal to the value of the Performance Share and/or Performance Unit, and all Performance Shares and Performance Units for which the performance period has not expired shall be cancelled in exchange for a cash payment equal to the product of: (1) the value of the Performance Shares and/or Performance Units that would have been earned if the Performance Goals (as measured at the time of the Change of Control) were to continue to be achieved at the same rate through the end of the performance period, or if higher, assuming the target Performance Goals had been met at the time of such Change of Control; and (2) a fraction, the numerator of which is the number of whole months that have elapsed from the beginning of the performance period to which the Award is subject to the date of the Change of Control and the denominator of which is the number of whole months in the performance period;

(D) all Annual and Long-Term Incentive Awards that are earned but not yet paid shall be paid, and all Annual and Long-Term Incentive Awards that are not yet earned shall be cancelled in exchange for a cash payment in an amount determined by taking the product of: (1) the amount that would have been due under such Award(s) if the Performance Goals (as measured at the time of the Change of Control) were to continue to be achieved at the same rate through the end of the performance period, or if higher, assuming the target Performance Goals had been met at the time of such Change of Control; and (2) a fraction, the numerator of which is the number of whole months that have elapsed from the beginning of the performance period to which the Award is subject to the date of the Change of Control and the denominator of which is the number of whole months in the performance period; and

(E) all Dividend Equivalent Units that are not vested shall vest and be paid in cash, and all other Awards that are not vested shall vest and if an amount is payable under such vested Award, such amount shall be paid in cash based on the value of the Award.

If the value of an Award is based on the Fair Market Value of a Share, Fair Market Value shall be deemed to mean the per share Change of Control Price. The Administrator shall determine the per share Change of Control Price paid or deemed paid in the Change of Control transaction. Notwithstanding anything to the contrary in this Section 16(c), the terms of any Awards that are subject to Code Section 409A shall govern the treatment of such Awards upon a Change of Control, and the terms of this Section 16(c) shall not apply, to the extent required for such Awards to remain compliant with Code Section 409A, as applicable.

(d) Application of Limits on Payments.

(i) Determination of Cap or Payment. Except to the extent the Participant has in effect an employment or similar agreement with the Company or any Affiliate or is subject to a policy that

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provides for a more favorable result to the Participant upon a Change of Control, if any payments or benefits paid by the Company pursuant to this Plan, including any accelerated vesting or similar provisions (“Plan Payments”), would cause some or all of the Plan Payments in conjunction with any other payments made to or benefits received by a Participant in connection with a Change of Control (such payments or benefits, together with the Plan Payments, the “Total Payments”) to be subject to the tax (“Excise Tax”) imposed by Code Section 4999 but for this Section 16(d), then, notwithstanding any other provision of this Plan to the contrary, the Total Payments shall be delivered either (A) in full or (B) in an amount such that the value of the aggregate Total Payments that the Participant is entitled to receive shall be One Dollar ($1.00) less than the maximum amount that the Participant may receive without being subject to the Excise Tax, whichever of (A) or (B) results in the receipt by the Participant of the greatest benefit on an after-tax basis (taking into account applicable federal, state and local income taxes and the Excise Tax).

(ii) Procedures.

(A) If a Participant or the Company believes that a payment or benefit due the Participant will result in some or all of the Total Payments being subject to the Excise Tax, then the Company, at its expense, shall obtain the opinion (which need not be unqualified) of nationally recognized tax counsel (“National Tax Counsel”) selected by the Company (which may be regular outside counsel to the Company), which opinion sets forth (1) the amount of the Base Period Income (as defined below), (2) the amount and present value of the Total Payments, (3) the amount and present value of any excess parachute payments determined without regard to any reduction of Total Payments pursuant to Section 6(a)(ii), and (4) the net after-tax proceeds to the Participant, taking into account applicable federal, state and local income taxes and the Excise Tax if (x) the Total Payments were delivered in accordance with Section 16(d)(i)(A) or (y) the Total Payments were delivered in accordance with Section 16(d)(i)(B). The opinion of National Tax Counsel shall be addressed to the Company and the Participant and shall be binding upon the Company and the Participant. If such National Tax Counsel opinion determines that Section 16(d)(i)(B) applies, then the Plan Payments or any other payment or benefit determined by such counsel to be includable in the Total Payments shall be reduced or eliminated so that under the bases of calculations set forth in such opinion there will be no excess parachute payment. In such event, payments or benefits included in the Total Payments shall be reduced or eliminated by applying the following principles, in order: (1) the payment or benefit with the higher ratio of the parachute payment value to present economic value (determined using reasonable actuarial assumptions) shall be reduced or eliminated before a payment or benefit with a lower ratio; (2) the payment or benefit with the later possible payment date shall be reduced or eliminated before a payment or benefit with an earlier payment date; and (3) cash payments shall be reduced prior to non-cash benefits; provided that if the foregoing order of reduction or elimination would violate Code Section 409A, then the reduction shall be made pro rata among the payments or benefits included in the Total Payments (on the basis of the relative present value of the parachute payments).

(B) For purposes of this Section 16: (1) the terms “excess parachute payment” and “parachute payments” shall have the meanings given in Code Section 280G and such “parachute payments” shall be valued as provided therein; (2) present value shall be calculated in accordance with Code Section 280G(d)(4); (3) the term “Base Period Income” means an amount equal to the Participant’s “annualized includible compensation for the base period” as defined in Code Section 280G(d)(1); (4) for purposes of the opinion of National Tax Counsel, the value of any noncash benefits or any deferred payment or benefit shall be determined by the Company’s independent auditors in accordance with the principles of Code Sections 280G(d)(3) and (4); and (5) the Participant shall be deemed to pay federal income tax and employment taxes at the highest marginal rate of federal income and employment taxation, and state and local income taxes at the highest marginal rate of taxation in the state or locality of the Participant’s domicile, net of the maximum reduction in federal income taxes that may be obtained from the deduction of such state and local taxes.

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(C) If National Tax Counsel so requests in connection with the opinion required by this Section 16(d)(ii), the Company shall obtain, at the Company’s expense, and the National Tax Counsel may rely on, the advice of a firm of recognized executive compensation consultants as to the reasonableness of any item of compensation to be received by the Participant solely with respect to its status under Code Section 280G.

(D) The Company agrees to bear all costs associated with, and to indemnify and hold harmless the National Tax Counsel from, any and all claims, damages and expenses resulting from or relating to its determinations pursuant to this Section 16, except for claims, damages or expenses resulting from the gross negligence or willful misconduct of such firm.

(E) This Section 16 shall be amended to comply with any amendment or successor provision to Code Section 280G or Code Section 4999. If such provisions are repealed without successor, then this Section 16 shall be cancelled without further effect.

17. Miscellaneous.

(a) Other Terms and Conditions. The Administrator may provide in any Award agreement such other provisions (whether or not applicable to the Award granted to any other Participant) as the Administrator determines appropriate to the extent not otherwise prohibited by the terms of the Plan.

(b) Employment and Service. The issuance of an Award shall not confer upon a Participant any right with respect to continued employment or service with the Company or any Affiliate, or the right to continue as a Director. Unless determined otherwise by the Administrator, for purposes of the Plan and all Awards, the following rules shall apply:

(i) a Participant who transfers employment between the Company and its Affiliates, or between Affiliates, will not be considered to have terminated employment;

(ii) a Participant who ceases to be a Non-Employee Director because he or she becomes an employee of the Company or an Affiliate shall not be considered to have ceased service as a Director with respect to any Award until such Participant’s termination of employment with the Company and its Affiliates;

(iii) a Participant who ceases to be employed by the Company or an Affiliate and immediately thereafter becomes a Non-Employee Director, a non-employee director of an Affiliate, or a consultant to the Company or any Affiliate shall not be considered to have terminated employment until such Participant’s service as a director of, or consultant to, the Company and its Affiliates has ceased; and

(iv) a Participant employed by an Affiliate will be considered to have terminated employment when such entity ceases to be an Affiliate.

Notwithstanding the foregoing, for purposes of an Award that is subject to Code Section 409A, if a Participant’s termination of employment or service triggers the payment of compensation under such Award, then the Participant will be deemed to have terminated employment or service upon his or her “separation from service” within the meaning of Code Section 409A. Notwithstanding any other provision in this Plan or an Award to the contrary, if any Participant is a “specified employee” within the meaning of Code Section 409A as of the date of his or her “separation from service” within the meaning of Code Section 409A, then, to the extent required by Code Section 409A, any payment made to the Participant on account of such separation from service shall not be made before a date that is six months after the date of the separation from service.

(c) No Fractional Shares. No fractional Shares or other securities may be issued or delivered pursuant to this Plan, and the Administrator may determine whether cash, other securities or other property will be paid or transferred in lieu of any fractional Shares or other securities, or whether such fractional Shares or other securities or any rights to fractional Shares or other securities will be canceled, terminated or otherwise eliminated.

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(d) Unfunded Plan; Awards Not Includable for Benefits Purposes. This Plan is unfunded and does not create, and should not be construed to create, a trust or separate fund with respect to this Plan’s benefits. This Plan does not establish any fiduciary relationship between the Company and any Participant or other person. To the extent any person holds any rights by virtue of an Award granted under this Plan, such rights are no greater than the rights of the Company’s general unsecured creditors. Income recognized by a Participant pursuant to an Award shall not be included in the determination of benefits under any employee pension benefit plan (as such term is defined in Section 3(2) of the Employee Retirement Income Security Act of 1974, as amended) or group insurance or other benefit plans applicable to the Participant which are maintained by the Company or any Affiliate, except as may be provided under the terms of such plans or determined by resolution of the Board.

(e) Requirements of Law and Securities Exchange. The granting of Awards and the issuance of Shares in connection with an Award are subject to all applicable laws, rules and regulations and to such approvals by any governmental agencies or national securities exchanges as may be required. Notwithstanding any other provision of this Plan or any award agreement, the Company has no liability to deliver any Shares under this Plan or make any payment unless such delivery ~~please follow~~or payment would comply with all applicable laws and the ~~instructions above~~applicable requirements of any securities exchange or similar entity, and unless and until the Participant has taken all actions required by the Company in connection therewith. The Company may impose such restrictions on any Shares issued under the Plan as the Company determines necessary or desirable to ~~vote using~~comply with all applicable laws, rules and regulations or the ~~Internet~~requirements of any national securities exchanges.

(f) Governing Law; Venue. This Plan, and ~~when prompted, indicate that you~~all agreements under this Plan, will be construed in accordance with and governed by the laws of the State of New York, without reference to any conflict of law principles. Any legal action or proceeding with respect to this Plan, any Award or any award agreement, or for recognition and enforcement of any judgment in respect of this Plan, any Award or any award agreement, may only be brought and determined in (i) a court sitting in the State of New York, and (ii) a “bench” trial, and any party to such action or proceeding shall agree to ~~receive~~waive its right to a jury trial.

(g) Limitations on Actions. Any legal action or ~~access proxy materials electronically in future years. VOTE BY PHONE - 1-800-690-6903 Use~~proceeding with respect to this Plan, any ~~touch-tone telephone~~Award or any award agreement, must be brought within one year (365 days) after the day the complaining party first knew or should have known of the events giving rise to ~~transmit your voting instructions. Vote by 11:59 P.M. ET on 01/24/2024. Have your proxy card in hand when you call and then follow~~ the ~~instructions. VOTE BY MAIL Mark, sign and date your proxy card and return it~~complaint.

(h) Construction. Whenever any words are used herein in the ~~postage-paid envelope we~~masculine, they shall be construed as though they were used in the feminine in all cases where they would so apply; and wherever any words are used in the singular or plural, they shall be construed as though they were used in the plural or singular, as the case may be, in all cases where they would so apply. Titles of sections are for general information only, and this Plan is not to be construed with reference to such titles.

(i) Severability. If any provision of this Plan or any award agreement or any Award (a) is or becomes or is deemed to be invalid, illegal or unenforceable in any jurisdiction, or as to any person or Award, or (b) would disqualify this Plan, any award agreement or any Award under any law the Administrator deems applicable, then such provision should be construed or deemed amended to conform to applicable laws, or if it cannot be so construed or deemed amended without, in the determination of the Administrator, materially altering the intent of this Plan, Award agreement or Award, then such provision should be stricken as to such jurisdiction, person or Award, and the remainder of this Plan, such Award agreement and such Award will remain in full force and effect.

18. Definitions. Capitalized terms used in this Plan or any Award agreement have the following meanings, unless the Award agreement otherwise provides:

(a) “Administrator” means the Committee; provided that, to the extent the Board has retained authority and responsibility as an Administrator of the Plan, the term “Administrator” shall also mean the Board or, to the extent the Committee has delegated authority and responsibility as an Administrator of the Plan to one or more officers of the Company as permitted by Section 2(b), the term “Administrator” shall also mean such officer or officers.

(b) “Affiliate” shall have the meaning given in Rule 12b-2 under the Exchange Act. Notwithstanding the foregoing, for purposes of determining those individuals to whom an Option or Stock Appreciation

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Right may be granted, the term “Affiliate” means any entity that, directly or through one or more intermediaries, is controlled by, controls, or is under common control with, the Company within the meaning of Code Sections 414(b) or (c); provided that, in applying such provisions, the phrase “at least 20 percent” shall be used in place of “at least 80 percent” each place it appears therein.

(c) “Award” means a grant of Options, Stock Appreciation Rights, Performance Shares, Performance Units, Restricted Stock, Restricted Stock Units, Shares, an Annual Incentive Award, a Long-Term Incentive Award, Dividend Equivalent Units or any other type of award permitted under the Plan.

(d) “Board” means the Board of Directors of the Company.

(e) “Cause” means any of the following as determined by the Company: (i) with respect to Participants other than Non-Employee Directors, the definition set forth in any employment or similar agreement between the Company or its Affiliates and the Participant or, if no such definition exists, (A) the failure of the Participant to perform or observe any of the material terms or provisions of any written agreement between the Participant and the Company or its Affiliates or, if no written agreement exists, the gross dereliction of the Participant’s duties (for reasons other than the Participant’s Disability) with respect to the Company or its Affiliates; (B) the failure of the Participant to comply fully with the lawful directives of the Board or the board of directors of an Affiliate of the Company, as applicable, or the officers or supervisory employees to whom the Participant reports; (C) the Participant’s dishonesty, misconduct, misappropriation of funds, or disloyalty or disparagement of the Company, any of its Affiliates or its management or employees; or (D) other proper cause determined in good faith by the Administrator; or (ii) with respect to Non-Employee Directors, (A) fraud or intentional misrepresentation; (B) embezzlement, misappropriation or conversion of assets or opportunities of the Company or any of its Affiliates; or (C) any other gross or willful misconduct as determined by the Committee, in its sole and conclusive discretion.

(f) “Change of Control” means the first to occur of the following with respect to the Company or any upstream holding company (which, for purposes of this definition, shall be included in references to “the Company”):

(i) Any “Person,” as that term is defined in Sections 13(d) and 14(d) of the Exchange Act, but excluding the Company, any trustee or other fiduciary holding securities under an employee benefit plan of the Company, or any corporation owned, directly or indirectly, by the stockholders of the Company in substantially the same proportions as their ownership of stock of the Company, is or becomes the “Beneficial Owner” (as that term is defined in Rule 13d-3 under the Exchange Act), directly or indirectly, of securities of the Company representing thirty-five percent (35%) or more of the combined voting power of the Company’s then outstanding securities; or

(ii) The consummation of a transaction in which the Company is merged or consolidated with any other corporation or other entity, other than: (A) a merger or consolidation which would result in the voting securities of the Company outstanding immediately prior thereto continuing to represent (either by remaining outstanding or by being converted into voting securities of the surviving entity) more than sixty-five percent (65%) of the combined voting power of the voting securities of the Company or such surviving entity outstanding immediately after such merger or consolidation; or (B) the Company engages in a merger or consolidation effected to implement a recapitalization of the Company (or similar transaction) in which no “Person” (as defined above) acquires thirty-five percent (35%) or more of the combined voting power of the Company’s then outstanding securities. Notwithstanding the foregoing, a merger or consolidation involving the Company shall not be considered a “Change of Control” if the Company is the surviving corporation and shares of the Stock are not converted into or exchanged for stock or securities of any other corporation, cash or any other thing of value, unless persons who beneficially owned shares of the Stock outstanding immediately prior to such transaction own beneficially less than a majority of the outstanding voting securities of the Company immediately following the merger or consolidation;

(iii) The consummation of a transaction in which the Company or any Affiliate sells, assigns or otherwise transfers assets in a transaction or series of related transactions, if the aggregate market value of the assets so sold, assigned or otherwise transferred exceeds thirty-five percent (35%) of the

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Company’s consolidated book value, determined by the Company in accordance with generally accepted accounting principles, measured at the time at which such transaction occurs or the first of such series of related transactions occurs; provided that such a transfer effected pursuant to a spin-off or split-up where stockholders of the Company retain ownership of the transferred assets proportionate to their pro rata ownership interest in the Company shall not be deemed a “Change of Control”;

(iv) The Company dissolves and liquidates substantially all of its assets; or

(v) At any time after the Effective Date when the “Continuing Directors” cease to constitute a majority of the Board. For this purpose, a “Continuing Director” shall mean: (A) the individuals who, at the Effective Date, constitute the Board; and (B) any new Directors (other than Directors designated by a person who has entered into an agreement with the Company to effect a transaction described in clause (i), (ii), or (iii) of this definition) whose appointment to the Board or nomination for election by Company stockholders was approved by a vote of at least two-thirds of the then-serving Continuing Directors.

If an Award is considered deferred compensation subject to the provisions of Code Section 409A, then the Administrator may include an amended definition of “Change of Control” in the Award agreement issued with respect to such Award as necessary to comply with, or as necessary to permit a deferral under, Code Section 409A.

(g) “Change of Control Price” means the highest of the following: (i) the Fair Market Value of the Shares, as determined on the date of the Change of Control; (ii) the highest price per Share paid in the Change of Control transaction; or (iii) the Fair Market Value of the Shares, calculated on the date of surrender of the relevant Award in accordance with Section 16(c), but this clause (iii) shall not apply if in the Change of Control transaction, or pursuant to an agreement to which the Company is a party governing the Change of Control transaction, all of the Shares are purchased for and/or converted into the right to receive a current payment of cash and no other securities or other property.

(h) “Code” means the Internal Revenue Code of 1986, as amended. Any reference to a specific provision of the Code includes any successor provision and the regulations promulgated under such provision.

(i) “Committee” means the Compensation Committee of the Board, or such other committee of the Board that is designated by the Board with the same or similar authority. The Committee shall consist only of Non-Employee Directors (not fewer than two (2)) within the meaning of Rule 16b-3 promulgated under the Exchange Act.

(j) “Company” means 22nd Century Group, Inc., a Nevada corporation, or any successor thereto.

(k) “Director” means a member of the Board; and “Non-Employee Director” means a Director who is not also an employee of the Company or its Subsidiaries.

(l) “Disability” means disability as defined in the Company’s long-term disability plan covering exempt salaried employees, except as otherwise determined by the Administrator and set forth in an Award agreement. The Administrator shall make the determination of Disability and may request such evidence of disability as it reasonably determines.

(m) “Dividend Equivalent Unit” means the right to receive a payment, in cash or Shares, equal to the cash dividends or other distributions paid with respect to a Share as described in Section 11.

(n) “Exchange Act” means the Securities Exchange Act of 1934, as amended. Any reference to a specific provision of the Exchange Act includes any successor provision and the regulations and rules promulgated under such provision.

(o) “Fair Market Value” means, per Share on a particular date, the last sales price on such date on the national securities exchange on which the Stock is then traded, as reported in The Wall Street Journal, or if no sales of Stock occur on the date in question, on the last preceding date on which there was a sale on such exchange. If the Shares are not listed on a national securities exchange, but are traded in an over-the-counter market, the last sales price (or, if there is no last sales price reported, the average of the

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closing bid and asked prices) for the Shares on the particular date, or on the last preceding date on which there was a sale of Shares on that market, will be used. If the Shares are neither listed on a national securities exchange nor traded in an over-the-counter market, the price determined by the Administrator, in its discretion, will be used. If an actual sale of a Share occurs on the market, then the Company may consider the sale price to be the Fair Market Value of such Share.

(p) “Good Reason” means, except as otherwise determined by the Administrator and set forth in an Award agreement:

(i) any breach by the Company of any employment or similar agreement between the Company (including, for purposes of this definition of Good Reason, any successor to the Company in a Change of Control) and the Participant, other than an isolated, insubstantial and inadvertent failure not occurring in bad faith that the Company remedies promptly after receipt of notice thereof given by the Participant;

(ii) any reduction in the Participant’s base salary, percentage of base salary available as incentive compensation or bonus opportunity or benefits, in each case relative to those most favorable to the Participant in effect at any time during the 180-day period prior to the Change of Control or, to the extent more favorable to the Participant, those in effect at any time after the Change of Control;

(iii) the removal of the Participant from, or any failure to reelect or reappoint the Participant to, any of the positions held with the Company on the date of the Change of Control or any other positions with the Company to which the Participant shall thereafter be elected, appointed or assigned, except in the event that such removal or failure to reelect or reappoint relates to the termination by the Company of the Participant’s employment for Cause or by reason of Disability;

(iv) a good faith determination by the Participant that there has been a material adverse change, without the Participant’s written consent, in the Participant’s working conditions or status with the Company relative to the most favorable working conditions or status in effect during the 180-day period prior to the Change of Control or, to the extent more favorable to the Participant, those in effect at any time after the Change of Control, including but not limited to (A) a significant change in the nature or scope of the Participant’s authority, powers, functions, duties or responsibilities, or (B) a significant reduction in the level of support services, staff, secretarial and other assistance, office space and accoutrements, but in each case excluding for this purpose an isolated, insubstantial and inadvertent event not occurring in bad faith that the Company remedies within ten (10) days after receipt of notice thereof given by the Participant;

(v) the relocation of the Participant’s principal place of employment to a location more than 50 miles from the Participant’s principal place of employment on the date 180 days prior to the Change of Control;

(vi) the Company requires the Participant to travel on Company business 20% in excess of the average number of days per month the Participant was required to travel during the 180-day period prior to the Change of Control; or

(vii) failure by the Company to obtain an agreement from any purchaser, assignee or transferee of substantially all of the Company’s business and assets, or the survivor in a merger, consolidation or combination with the Company, to expressly assume and agree to perform from and after the date of such assignment all of the terms, conditions and provisions imposed by an employment or similar agreement between the Participant and the Company.

A Participant’s termination shall not be considered to have occurred for “Good Reason” unless (A) within ninety (90) days following the occurrence of one of the events listed above the Participant provides written notice to the Company setting forth the specific event constituting Good Reason, (B) the Company fails to remedy the event constituting Good Reason within thirty (30) days following its receipt of the Participant’s notice, and (C) the Participant actually terminates his or her employment with the Company and its Affiliates within thirty (30) days following the end of the Company’s remedy period.

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(q) “Incentive Award” means the right to receive a cash payment to the extent Performance Goals are achieved (or other requirements are met), and shall include “Annual Incentive Awards” as described in Section 9 and “Long-Term Incentive Awards” as described in Section 10.

(r) “Option” means the right to purchase Shares at a stated price for a specified period of time.

(s) “Participant” means an individual selected by the Administrator to receive an Award.

(t) “Performance Goals” means any objective or subjective goals the Administrator establishes with respect to an Award. Performance Goals may include, but are not limited to, goals that relate to one or more of the following with respect to the Company or any one or more of its Subsidiaries, Affiliates or other business units: net sales; earnings before interest and taxes; earnings before interest, taxes, depreciation and amortization; Fair Market Value of Shares; basic earnings per share; diluted earnings per share; return on stockholder equity; return on average equity; return on average total capital employed; return on net assets employed before interest and taxes; economic value added; return on year-end equity; capital; cost of capital; cost of equity; cost of debt; taxes; market share; operating ratios; productivity measurements; revenue to budget compliance; net income to budget compliance; return on total awards reinvestment; net free cash flow; new sales; divisional profitability; customer satisfaction measurements; production quotas; project criteria or a combination of the foregoing. As to each Performance Goal, the relevant measurement of performance shall, unless otherwise determined by the Administrator at any time, be computed in accordance with generally accepted accounting principles, if applicable; provided that, the Administrator may, at the time of establishing the Performance Goal(s), exclude the effects of (i) extraordinary, unusual and/or non-recurring items of gain or loss, (ii) gains or losses on the disposition of a business, (iii) changes in tax or accounting regulations or laws, or (iv) the effect of a merger or acquisition. In addition, the Administrator may appropriately adjust any evaluation of performance under a Performance Goal to exclude any of the following events that occurs during a performance period: (i) litigation, claims, judgments or settlements; (ii) the effects of changes in other laws or regulations affecting reported results; and (iii) accruals of any amounts for payment under this Plan or any other compensation arrangements maintained by the Company. Where applicable, the Performance Goals may be expressed, without limitation, in terms of attaining a specified level of the particular criterion or the attainment of an increase or decrease (expressed as absolute numbers, averages and/or percentages) in the particular criterion or achievement in relation to a peer group or other index. The Performance Goals may include a threshold level of performance below which no payment will be made (or no vesting will occur), levels of performance at which specified payments will be paid (or specified vesting will occur), and a maximum level of performance above which no additional payment will be made (or at which full vesting will occur). In addition, the Administrator may establish other Performance Goals and provide for other exclusions or adjustments not listed in this Plan.

(u) “Performance Shares” means the right to receive Shares to the extent Performance Goals are achieved (or other requirements are met) as described in Section 8.

(v) “Performance Unit” means the right to receive a cash payment and/or Shares valued in relation to a unit that has a designated dollar value or the value of which is equal to the Fair Market Value of one or more Shares, to the extent Performance Goals are achieved (or other requirements are met) as described in Section 8.

(w) “Person” has the meaning given in Section 3(a)(9) of the Exchange Act, as modified and used in Sections 13(d) and 14(d) thereof, or any group of Persons acting in concert that would be considered “persons acting as a group” within the meaning of Treas. Reg. § 1.409A-3(i)(5).

(x) “Plan” means this 22nd Century Group, Inc. 2021 Omnibus Incentive Plan, as amended and restated and as it may be further amended from time to Vote Processing, c/o Broadridge, 51 Mercedes Way, Edgewood, NY 11717. NAME THE COMPANY NAME INC. - COMMON THE COMPANY NAME INC. - CLASS A THE COMPANY NAME INC. - CLASS B THE COMPANY NAME INC. - CLASS C THE COMPANY NAME INC. - CLASS D THE COMPANY NAME INC. - CLASS E THE COMPANY NAME INC. - CLASS F THE COMPANY NAME INC. - 401 K TOtime.

(y) “Restricted Stock” means a Share that is subject to a risk of forfeiture or restrictions on transfer, or both a risk of forfeiture and restrictions on transfer, as described in Section 8.

(z) “Restricted Stock Unit” means the right to receive a cash payment and/or Shares equal to the Fair Market Value of one Share that is subject to a risk of forfeiture or restrictions on transfer, or both a risk of forfeiture and restrictions on transfer, as described in Section 8.

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(aa) “Section 16 Participants” means Participants who are subject to the provisions of Section 16 of the Exchange Act.

(bb) “Share” means a share of Stock.

(cc) “Stock” means the common stock, par value $0.00001 per share, of the Company.

(dd) “Stock Appreciation Right” or “SAR” means the right to receive cash, and/or Shares with a Fair Market Value, equal to the appreciation of the Fair Market Value of a Share during a specified period of time.

(ee) “Subsidiary” means any corporation, limited liability company or other limited liability entity in an unbroken chain of entities beginning with the Company if each of the entities (other than the last entities in the chain) owns the stock or equity interest possessing more than fifty percent (50%) of the total combined voting power of all classes of stock or other equity interests in one of the other entities in the chain.

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Signature [PLEASE SIGN WITHIN BOX] Date Signature (Joint Owners) DateTO VOTE, MARK BLOCKS BELOW IN BLUE OR BLACK INK AS FOLLOWS: x CONTROL # → SHARES 123,456,789,012.12345 123,456,789,012.12345 123,456,789,012.12345 123,456,789,012.12345 123,456,789,012.12345 123,456,789,012.12345 123,456,789,012.12345 123,456,789,012.12345 PAGE 1 OF 2 KEEP THIS PORTION FOR YOUR ~~RECORDS THIS~~RECORDSTHIS PROXY CARD IS VALID ONLY WHEN SIGNED AND DATED. DETACH AND RETURN THIS PORTION ~~ONLY The Board of Directors recommends you vote FOR the following proposals: For Against Abstain 1.~~ONLYV51242-P137131. To approve an amendment to ~~our~~the Company’s Amendedand Restated Articles of Incorporation ~~as amended,~~ to ~~effect a reverse stock split~~declassify theBoard of ~~our outstanding common stock at a ratio between 1-for-2 and 1-for-16,~~Directors (the “Charter Amendment”).2. If the Charter Amendment is approved, to ~~be determined at the discretion of our board of directors (the “Reverse Split”), for the purpose of complying with the Nasdaq Listing Rules, subject~~elect fourdirectors to the ~~Board’s discretion to abandon such amendment (Proposal 1). 2.~~Board of Directors.5. To approve anthe amendment ~~to our Articles~~and restatement of ~~Incorporation, as amended, to~~the22nd Century Group, Inc. 2021 Omnibus Incentive Planwhich shall increase the number of shares authorized ~~shares~~forissuance by five million (5,000,000).2c. Anthony Johnson2a. Lawrence FirestoneNominees:2b. Andrew Arno4. To approve, by non-binding vote, 2023 executivecompensation.2d. Lucille Salhany3. If the Charter Amendment is not approved, to electAndrew Arno as a Class I director.8. Ratification of ~~common stock from sixty-six million, six hundred sixty-six thousand sixty hundred sixty-seven (66,666,667) shares to [two hundred fifty million] ([250,000,000]) (Proposal 2). 3.~~the appointment of Freed Maxick CPAs,P.C. as our independent registered public accountants forfiscal year 2024.6. To approve the ~~issuance of shares of common stock~~Warrants dated April 9, 2024 and theshares issuable upon exercise of the warrants ~~to purchase common stock (the “Inducement Warrants”) issued to accredited investors~~pursuantto Rule 5635(d) of the Nasdaq Stock Market.7. To approve the Voluntary Conversion Option inthe Debentures dated March 3, 2023, as amendedDecember 22, 2023, pursuant to ~~warrant inducement agreements in accordance with the terms~~Rules 5635(b) and5635(d) of the ~~Inducement Warrants, as required by and in accordance with~~ Nasdaq ~~Listing Rules (Proposal 3) (Proposal 3). 4.~~Stock Market.9. To approve the adjournment of the meeting, if necessary ~~or advisable,~~oradvisable, to solicit additional proxies in favor of ~~Proposals 1, 2 and/~~the CharterAmendment (Proposal 1), the amendment and restatementof our 2021 Omnibus Incentive Plan (Proposal 5), theapproval of the Warrants (Proposal 6) or 3the approval ofthe Voluntary Conversion Option (Proposal ~~4). NOTE: Such other business as may properly come before the meeting or any adjournment thereof. Investor Address Line 1 Investor Address Line 2 Investor Address Line 3 Investor Address Line 4 Please~~7).For Against Abstain! ! !! ! !! ! !! ! !! ! !! ! !! ! !! ! !! ! !! ! !Please sign exactly as your name(s) appear(s) hereon. When signing as attorney, executor,administrator, or other fiduciary, please give full title as such. Joint owners should each ~~sign personally.~~signpersonally. All

holders must sign. If a corporation or partnership, please sign in full ~~corporate or~~corporateor partnership name by authorized ~~officer. Investor Address Line John Sample 1234 ANYWHERE STREET ANY CITY, ON A1A 1A1~~officer.22ND CENTURY GROUP, INC.THE BOARD OF DIRECTORS RECOMMENDS A VOTE FORPROPOSALS 1, 4, 5, ~~Signature [PLEASE SIGN WITHIN BOX] Date JOB # Signature (Joint Owners) Date SHARES CUSIP # SEQUENCE #~~6, 7, 8 AND 9, AND "FOR" ALL OF THENOMINEES FOR DIRECTORS LISTED IN PROPOSALS 2 AND 3.BROADRIDGE CORPORATE ISSUER SOLUTIONSC/O 22ND CENTURY GROUP, INC.P.O. BOX 1342BRENTWOOD, NY 11717For Against Abstain! ! !! ! !VOTE BY INTERNET - www.proxyvote.com or scan the QR Barcode aboveUse the Internet to transmit your voting instructions and for electronic deliveryof information. Vote by 11:59 p.m. Eastern Time on June 27, 2024. Have yourproxy card in hand when you access the web site and follow the instructions toobtain your records and to create an electronic voting instruction form.ELECTRONIC DELIVERY OF FUTURE PROXY MATERIALSIf you would like to reduce the costs incurred by our company in mailing proxymaterials, you can consent to receiving all future proxy statements, proxy cardsand special reports electronically via e-mail or the Internet. To sign up for electronicdelivery, please follow the instructions above to vote using the Internet and,when prompted, indicate that you agree to receive or access proxy materialselectronically in future years.VOTE BY PHONE - 1-800-690-6903Use any touch-tone telephone to transmit your voting instructions. Vote by11:59 p.m. Eastern Time on June 27, 2024. Have your proxy card in hand whenyou call and then follow the instructions.VOTE BY MAILMark, sign and date your proxy card and return it in the postage-paidenvelope we have provided or return it to Vote Processing, c/o Broadridge,51 Mercedes Way, Edgewood, NY 11717.SCAN TOVIEW MATERIALS & VOTE

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Important Notice Regarding the Availability of Proxy Materials for the Annual Meeting:The Annual Report and Notice and Proxy Statement are available at www.proxyvote.com.V51243-P1371322ND CENTURY GROUP, INC.THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF DIRECTORSANNUAL MEETING OF STOCKHOLDERSJUNE 28, 2024The stockholder(s) hereby appoint(s) Lawrence D. Firestone and Jonathan Staffeldt or any of them, as proxies, each with the power to appoint his substitute, and hereby authorize(s) them to represent and to vote, as designated on the reverse side of this ballot, all of the shares of common stock of 22ND CENTURY GROUP, INC. that the stockholder(s) is/are entitled to vote at theAnnual Meeting of Stockholders to be held at 11:00 a.m., Eastern Time on Friday, June 28, 2024, to be held at11988 El Camino Real, Suite 400, San Diego, CA 92130, and any adjournment or postponement thereof.THIS PROXY, WHEN PROPERLY EXECUTED, WILL BE VOTED AS DIRECTED BY THE STOCKHOLDER(S). IF NO SUCH DIRECTIONS ARE MADE, THIS PROXY WILL BE VOTED FOR THE ELECTION OF THE NOMINEES LISTED ON THE REVERSE SIDE FOR THE BOARD OF DIRECTORS AND FOR PROPOSALS 1, 4, 5, 6, 7, 8 AND 9.Continued and to be signed on reverse side

Proposed Ratio	Number of Shares of Common Stock Authorized		Approximate Number of Shares of Common Stock Outstanding		Approximate Number of Unreserved Shares of Common Stock Available for Future Issuance
1-for-2(1)		66,666,667		21,889,528		20,470,730
1-for-16(1)		66,666,667		2,736,191		60,892,174