Company: XXII
Filing Date: 2025-11-04
Form Type: 424B5
Source: 0001493152-25-020754
Chunk: 13

Company: 22nd Century Group, Inc.
Filing Date: 2025-11-04
Form: 424B5
Chunk 13
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 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-10 |

<div align='center'>Plan of Distribution</div>

We have entered into the Sales Agreement with the Sales Agent relating to the sale of shares of our common stock offered by this prospectus supplement. Under this prospectus supplement, in accordance with the terms of the Sales Agreement, we may sell shares of our common stock for an aggregate offering price of up to $25,000,000 from time to time through or to the Sales Agent, acting as the sales agent, subject to certain limitations, including the number or dollar amount of shares registered under the registration statement to which the offering relates. The sales, if any, of shares made under the Sales Agreement may be made in negotiated transactions, including block trades or block sales, or by any method permitted by law that is deemed to be an “at the market offering” as defined in Rule 415 promulgated under the Securities Act, including without limitation sales made
through Nasdaq or an any other existing trading market for our common stock, or by any other method permitted by law. Sales pursuant
to the Sales Agreement may be made through an affiliate of the Sales Agent. We may instruct the Sales Agent not to sell common
stock if the sales cannot be effected at or above the price designated by us from time to time. We or the Sales Agent may
suspend the offering of common stock upon notice and subject to other conditions.

Pursuant to the terms
of the securities purchase agreement we entered into in connection with the issuance of the Series A Preferred Stock, we may only sell
shares in an at the market offering on a trading day between 9:30 a.m. and 4:00 p.m. (New York City time) (a) up to 5% of the daily volume
if the stock trades above 125% of the Conversion Price of the Series A Preferred Stock, and (b) up to 10% of the daily volume if stock
trades above 150% of the Conversion Price.

Each time we wish to issue
and sell common stock under the Sales Agreement, we will notify the Sales Agent of the number or dollar value of shares to be issued,
the dates on which such sales are anticipated to be made, any minimum price below which sales may not be made and other sales parameters