Waiver and Amendment Agreement dated October 16, 2023

Exhibit 10.1

WAIVER AND AMENDMENT AGREEMENT

This Wavier and Amendment Agreement (the “Agreement”), dated as of October 16, 2023, is made by and between (i) 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 each a “Holder”), (ii) 22nd Century Group, Inc., a Nevada corporation (the “Company”), (iii) each of the subsidiaries of the Company executing this Agreement as guarantors (collectively, the “Subsidiary Guarantors”, and together with the Company, the “Company Parties”), and (iv) JGB Collateral, LLC, as collateral agent for the Holders (the “Agent”).

WHEREAS, the Holders and the Company are parties to that certain Securities Purchase Agreement, dated as of March 3, 2023 (as the same may be amended, amended and restated, supplemented or otherwise modified from time to time in accordance with its provisions, the “SPA”), whereby, among other things, (i) the Company has issued to the Holders, and the Holders have acquired from the Company, certain 7% Original Issue Discount Senior Secured Debentures due March 3, 2026, in the aggregate original principal amount of $21,052,632 (the “Debentures”) and certain Common Stock Purchase Warrants to purchase an aggregate of 496,960 shares of the Company’s common stock at an exercise price of $12.828 per share (the “Warrants”), (ii) each of the Subsidiary Guarantors have executed and delivered to the Agent that certain Subsidiary Guaranty (the “Guaranty”), dated March 3, 2022, pursuant to which each such Subsidiary Guarantor guaranteed, among other things, payment of the Obligations (as defined in such Guaranty), (iii) each Company Party executed and delivered to the Agent that certain Security Agreement (the “Security Agreement”), dated March 3, 2022, whereby each Company Party granted a first ranking lien and security interest in substantially all of its assets to the Agent as security for the Company Parties’ obligations under the Transaction Documents (as defined in the SPA), and (iv) the Company, the Agent and Truist Bank have entered into that certain Escrow Agreement, dated as of March 27, 2023, (the “Escrow Agreement”) pursuant to which Truist Bank maintains, in its capacity as escrow agent, possession of $7,500,000 of cash collateral for the for the Company Parties’ obligations under the Loan Documents (the “Escrow Funds”);

WHEREAS, the Company failed to achieve revenue (as determined in accordance with GAAP) of at least $18,500,000 for the quarter ended September 30, 2023 in accordance with pursuant to Section 7(d) of the Debentures resulting in the occurrence of an Event of Default, which is continuing, under the Debentures and the other Transaction Documents (the “Specified Default”); and

WHEREAS, the parties now desire to enter into this Agreement to, among other things, waive the Specified Default and to agree to such other matters set forth herein.

NOW, THEREFORE, in consideration of the premises set forth above and other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties agree as follows:

[SIGNATURE PAGE FOLLOWS]

IN WITNESS WHEREOF, the parties hereto have executed this Agreement as of the date first above written.

COMPANY:

22nd Century Group, Inc.

By: /s/ Peter Ferola
Name: Peter Ferola
Title: General Counsel & Corporate Secretary

HOLDERS AND AGENT:

JGB PARTNERS, LP

JGB CAPITAL LP

JGB CAPITAL OFFSHORE LTD.

JGB COLLATERAL LLC

By: /s/ Brett Cohen

Name: Brett Cohen

Title: President