Company: XXII
Filing Date: 2025-08-26
Form Type: 424B5
Source: 0001641172-25-025541
Chunk: 15

Company: 22nd Century Group, Inc.
Filing Date: 2025-08-26
Form: 424B5
Chunk 15
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 common stock at an exercise price of $18.15 (which were reduced to $1.97 per share   
 as a result of this offering).                                                                                                         |
| ● | 20,822                                                                                                                                 
 shares of our common stock issuable upon the exercise of fully vested and immediately exercisable stock options outstanding as of      
 June 30, 2025, at a weighted-average exercise price of  $46.23 per share;                                                              |
| ● | 6,946                                                                                                                                  
 shares of unvested restricted stock units; and                                                                                         |
| ● | 5,204,262                                                                                                                              
 shares of our common stock reserved for future award grants under the under the 22nd Century Group, Inc. 2021 Omnibus Incentive Plan.  |

To the extent outstanding options are exercised or outstanding restricted stock units vest, there will be further dilution to investors. In addition, to the extent that we issue additional equity securities in connection with future capital raising activities, our then-existing stockholders may experience dilution.

| S-8 |

<div align='center'>PLAN OF DISTRIBUTION</div>

Pursuant to an engagement agreement between us and Dawson James Securities, Inc. (“Dawson James” or the “placement agent”) we have engaged Dawson James as our exclusive placement agent to solicit offers to purchase the securities in this offering. The placement agent is not purchasing or selling any of the securities we are offering, and it is not required to arrange the purchase or sale of any specific number of securities or dollar amount, but it has agreed to use commercially reasonable efforts to arrange for the sale of the shares. The placement agent may retain sub-agents and selected dealers in connection with this offering.

The placement agent proposes to arrange for the sale of the securities we are offering pursuant to this prospectus supplement and the accompanying prospectus to one or more investors through securities purchase agreements directly between the purchasers and us. All of the securities will be sold at the same price and, we expect, at a single closing. We established the price following negotiations with prospective investors and with reference to the prevailing market price of our common stock, recent trends in such price and other factors. It is possible that not all of the securities we are offering pursuant to this prospectus supplement and the accompanying prospectus will be sold at the closing, in which case our net proceeds would be reduced. We anticipate that the sale of the securities will be completed on the date indicated on the cover page of this prospectus supplement, subject to customary