Company: XXII
Filing Date: 2025-08-26
Form Type: 424B5
Source: 0001641172-25-025541
Chunk: 0

Company: 22nd Century Group, Inc.
Filing Date: 2025-08-26
Form: 424B5
Chunk 0
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| Prospectus                       
 Supplement                       
 (To                              
 Prospectus dated March 31, 2023) |     | Filed                      
 Pursuant to Rule 424(b)(5) 
 Registration               
 No. 333-270473             |

<div align='center'>10,650 Shares of Series A Convertible Preferred Stock

Common Warrants to Purchase up to 9,460,661 Shares of Common Stock

Placement Agent Warrants to Purchase up to 567,641 Shares of Common Stock

Up to 14,891,315 Shares of Common Stock Underlying Such Series A Convertible Preferred Stock, Common Warrants and Placement Agent Warrants</div>

Pursuant to this prospectus supplement and the accompanying prospectus, we are offering 10,650 shares (the “Shares”) of newly-established shares of Series A Convertible Preferred Stock, stated value of $1,000 per share (“Series A Preferred Stock”), and warrants (the “Warrants”) to purchase 9,460,661 shares of the Company’s common stock, par value $0.00001 per share (“Common Stock”) for a combined purchase price of $10.65 million. The Warrants are immediately exercisable at an exercise price of $1.97 per share of Common Stock and expire on the date that is five (5) years after issuance. We are also registering pursuant to this prospectus supplement and the accompanying prospectus up to 4,863,013 shares of Common Stock issuable upon conversion of the Series A Preferred Stock using the initial conversion price of $2.19 per share and up to 9,460,661 shares of Common Stock issuable up exercise of the Warrants.

The Series A Preferred Stock is convertible into Common Stock at any time at an initial conversion price of $2.19 and, upon the receipt of stockholder approval, subject to adjustment for certain anti-dilution provisions set forth in the Series A Certificate of Designation, subject to a floor price of $0.394. The Company agreed to hold a meeting of stockholders within 90 days of closing to approve the issuance of the shares of Common Stock upon such anti-dilution adjustment and to call a meeting every 120 days thereafter if stockholder approval is not obtained at the initial meeting of stockholders (the “Stockholder Approval”). If Stockholder Approval is not obtained within 180 days, the holders may require the Company to redeem the Series A Preferred Stock at the stated value per share of each share of Series A Preferred Stock being redeemed