Exhibit 3.1

CERTIFICATE OF AMENDMENT OF

CERTIFICATE OF DESIGNATIONS OF

SERIES A CONVERTIBLE PREFERRED STOCK OF

22ND CENTURY GROUP, INC.

This Certificate of Amendment to the Certificate of Designations of Series A Convertible Preferred Stock (the “Amendment”) is dated as of [   ], 2025.

WHEREAS, the board of directors (the “Board”) of 22nd Century Group, Inc., a Nevada corporation (the “Company”), pursuant to the authority granted to it by the Company’s Certificate of Incorporation (as amended, the “Certificate of Incorporation”) has previously fixed the rights, preferences, restrictions and other matters relating to a series of the Company’s preferred stock, consisting of 10,650 authorized shares of preferred stock, classified as Series A Convertible Preferred Stock (the “Preferred Stock”), and the Certificate of Designations of the Preferred Stock (the “Certificate of Designations”) was initially filed with the Secretary of State of the State of Nevada on [   ], 2025, evidencing such terms;

WHEREAS, pursuant to Section 8(l) of the Certificate of Designations, the Certificate of Designations or any provision thereof may be amended by obtaining the written consent of the holders owning a majority of the shares of Preferred Stock issued and outstanding on such date (the “Required Holders”);

WHEREAS, the Required Holders pursuant to the Certificate of Designations have consented on [   ], 2025, to this Amendment on the terms set forth herein; and

WHEREAS, the Board has duly adopted resolutions proposing to adopt this Amendment and declaring this Amendment to be advisable and in the best interest of the Company and its stockholders.

NOW, THEREFORE, this Amendment has been duly adopted and has been executed by a duly authorized officer of the Company as of the date first set forth above to amend the terms of the Certificate of Designations as follows:

(g) Right of Alternate Conversion.

(i) General. Subject to Section 6(d), at any time after the Stockholder Approval Date, the Holder may, at the Holder’s option, convert (each, an “Alternate Conversion”, and the date of such Alternate Conversion, each, an “Alternate Conversion Date”) all, or any part of, the Conversion Amount (such portion of the Conversion Amount subject to such Alternate Conversion, each, an “Alternate Conversion Amount”) into shares of Common Stock at a conversion price equal to the higher of (i) 85% of the lowest daily VWAP in the twenty (20) Trading Days prior to the applicable Alternate Conversion Date, and (ii) the Floor Price (the “Alternate Conversion Price”).

(ii) Mechanics of Alternate Conversion. On any Alternate Conversion Date, the Holder may voluntarily convert any Alternate Conversion Amount pursuant to Section 6(g)(i) (with “Alternate Conversion Price” replacing “Conversion Price” for all purposes hereunder with respect to such Alternate Conversion) by designating in the Conversion Notice delivered pursuant to this Section 6(g)(ii) that the Holder is electing to use the Alternate Conversion Price for such conversion.

(h) Voluntary Adjustment by Company. Subject to the rules and regulations of the principal Market, the Company may at any time any shares of Preferred Stock remain outstanding, with the prior written consent of the Holders owning a majority of the shares of Preferred Stock issued and outstanding on such date, reduce the then current Conversion Price to any amount and for any period of time deemed appropriate by the Board of Directors, subject to the Floor Price.

[Signature Page Follows]

IN WITNESS WHEREOF, the Company has caused this Amendment to be signed by its duly authorized officer this [   ] day of December, 2025.

Exhibit 10.1

OMNIBUS AMENDMENT and waiver

This Omnibus Amendment and Waiver (this “Agreement”), dated as of [ ], 2025, is by and among 22nd Century Group, Inc., a Nevada corporation (the “Company”), and the signatories listed on the signature pages attached hereto (the “Investors”).

WITNESSETH

Whereas, the Company and certain investors, including certain of the Investors, are party to (i) that certain Securities Purchase Agreement, dated as of August 22, 2025 (the “Purchase Agreement”), pursuant to which the Company issued in a registered direct offering (the “Offering”) shares of the Company’s Series A Convertible Preferred Stock, par value $0.00001 per share (the “Preferred Stock”), the terms of which are set forth in the Certificate of Designations for the Series A Convertible Preferred Stock (the “Certificate of Designations”), and warrants (the “Investor Warrants” and, together with the Purchase Agreement and Certificate of Designations, the “Transaction Documents”) to purchase shares of the Company’s common stock, par value $0.00001 per share (the “Common Stock”), and (ii) that certain engagement letter, dated as of August 21, 2025, pursuant to which, in connection with the Offering, the Company issued placement agent warrants to purchase shares of Common Stock (the “Placement Agent Warrants” and, collectively with the Investor Warrants, the “Warrants”);

WHEREAS, pursuant to the Purchase Agreement, the Company is required to obtain Stockholder Approval on or prior to the date that is ninety (90) days following the Closing Date (the “Initial Stockholder Approval Deadline”);

WHEREAS, the Company has not obtained Stockholder Approval by the Initial Stockholder Approval Deadline;

WHEREAS, pursuant to (i) Section 8(l) of the Certificate of Designations, the Certificate of Designations or any provision thereof may be amended by the holders of a majority of the shares of Preferred Stock issued and outstanding, (ii) Section 5.5 of the Purchase Agreement, the Purchase Agreement may only be waived or amended by the Company and the purchasers of at least a majority in interest of the Preferred Shares based on the initial Subscription Amounts thereunder, and (iii) Section 5(l) of the Warrants, each Warrant may be amended with the written consent of the Company and the holder of each such Warrant;

WHEREAS, the Investors collectively hold at least a majority of the outstanding shares of Preferred Stock as of the date hereof and based on the initial Subscription Amount; and

WHEREAS, the Company and the Investors desire to waive and amend certain provisions of the Transaction Documents.

Now, therefore, in consideration of the premises and mutual covenants and obligations hereinafter set forth, the parties hereto, intending legally to be bound, hereby agree as follows:

“Stockholder Approval” means (i) such 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 the transactions contemplated by the Transaction Documents, including with respect to the issuance of the shares underlying the Preferred Shares and Warrants, including but not limited to with respect to a Dilutive Issuance (as each defined in the Certificate of Designations and Warrants), (ii) approval from the Company’s stockholders of an amendment to the Company’s Amended and Restated Certificate of Incorporation, as amended, to effect a reverse stock split of all of the outstanding shares of the Company’s Common Stock, for the purpose of complying with the Nasdaq Listing Rules, and (iii) approval from the Company’s stockholders of an offering of the Company’s securities, including preferred stock and warrants on substantially the same terms as the Securities under this Agreement, to be completed within three (3) months from the date of the stockholder meeting at which stockholder approval is obtained, in an aggregate amount not to exceed $20 million, with the initial conversion price of such preferred stock to equal to the Nasdaq Minimum Price (as defined in Nasdaq Listing Rule 5635(d)) and the initial exercise price of such warrants to equal the Nasdaq Minimum Price, in each case, as of the date the related binding agreement is executed.

Stockholder Approval. The Company shall hold an annual or special meeting of stockholders on or prior to February 23, 2026 (the “Stockholder Approval Deadline”), for the purpose of obtaining Stockholder Approval, with the recommendation of the Company’s Board of Directors that such proposals are approved, and the Company shall solicit proxies from its stockholders in connection therewith in the same manner as all other management proposals in such proxy statement and all management-appointed proxyholders shall vote their proxies in favor of such proposals. If the Company does not obtain Stockholder Approval at the first meeting, the Company shall call a meeting every one-hundred twenty (120) days thereafter to seek Stockholder Approval until the earlier of the Stockholder Approval Date or the Warrants are no longer outstanding. If the Stockholder Approval is not obtained by February 23, 2026, each Purchaser may require the Company to redeem all or any of the shares of Preferred Stock by delivering written notice thereof (the “Redemption Notice”) to the Company, which Redemption Notice shall indicate the number of shares of Preferred Stock the Purchaser is electing to redeem. Each share of Preferred Stock subject to redemption by the Company pursuant to the procedures specified in Section 6(f) of the Certificate of Designations and shall be redeemed in cash by the Company at a price equal to 100% of the Stated Value of each share of Preferred Stock being redeemed.

[Signature pages follow immediately.]

In witness whereof, the undersigned has executed and delivered this Agreement as of the date first above written.

In witness whereof, the undersigned has executed and delivered this Agreement as of the date first above written.

[Investor Signature Page to Omnibus Amendment]