22nd Century Group, Inc. (XXII) - Dilution Analysis

Visualizing historical and potential share dilution over time

Dilution Analysis

High Risk
Significant dilution risk
Last updated: May 07, 2026

Risk Assessment Details

Potential Dilution: 0.0% of current shares
Recent Dilution: 5186.88% (2 years)
Historical Dilution Factor: significant recent dilution
Outstanding Shares
4.5M
Potential Supply
0
Additional shares possible
Splits
3 Splits 3 Reverse
Past 2 years

Summary

XXII currently has 4.46M outstanding shares. with minimal authorized share overhang for future dilution. The company has significantly diluted shareholders by 5186.88% over the past 2 years, indicating aggressive capital raising. Recent corporate actions include 3 stock splits (positive for accessibility) and 3 reverse splits (concerning signal).

Share Structure Timeline

Outstanding Shares
Total Supply

Historical Data Points

Date Event Outstanding Supply
May 07, 2026

10-Q filing | 4.5M shares outstanding

4.5M 0
Mar 26, 2026

10-K filing | 0.7M shares outstanding

660K 0
Mar 20, 2026

8-K filing: 22nd Century Group, Inc. entered into a securities purchase agreement for the offer and sale of up to $20 million of Series B Convertible Preferred Stock and warrants to purchase common stock via a registered direct offering, with an initial closing of $16 million and a potential second closing of $4 million. ($16.0M proceeds)

510K 98K
Jan 26, 2026
Stock Split

8-K filing: Stock split 1-for-15 | Outstanding: 6,987,290 → 510,177

510K 98K
Nov 04, 2025

10-Q filing | 7.0M shares outstanding

7M 2.1M
Aug 14, 2025

10-Q filing | 3.7M shares outstanding

3.7M 5.4M
Jun 20, 2025

S-3 filing: This prospectus relates to the resale from time to time by the selling stockholders named in this prospectus of up to 8,588,811 shares of our common stock issuable upon the exercise of outstanding warrants.

12M 0
Jun 20, 2025
Stock Split

8-K filing: Stock split 1-for-23 | Outstanding: 11,507,622 → 500,331

500K 8.6M
May 13, 2025

10-Q filing | 11.5M shares outstanding

12M 640K
May 08, 2025

S-3 filing: This S-3 filing registers the resale of up to 11,272,093 shares of common stock by selling stockholders, including shares of common stock and shares issuable upon the exercise of outstanding warrants.

2.4M 9.8M
Mar 20, 2025

10-K filing | 2.4M shares outstanding

2.4M 0
Feb 05, 2025

S-3/A filing: This S-3/A filing, dated February 5, 2025, relates to the resale of up to 104,124 shares of common stock by selling stockholders.

550K 330K
Jan 31, 2025

S-3 filing: This S-3 filing pertains to the resale of up to 104,124 shares of common stock by selling stockholders, with the company not receiving any proceeds from the sale.

550K 330K
Dec 17, 2024
Stock Split

8-K filing: Stock split 1-for-135 | Outstanding: 2,720,437 → 553,516

550K 220K
Nov 12, 2024

10-Q filing | 2.7M shares outstanding

2.7M 100M
Nov 01, 2024

S-3 filing: This S-3 filing registers up to 93,619,716 shares of common stock for resale by selling stockholders, issuable upon the exercise of outstanding warrants from various private placements.

46M 59M
Oct 24, 2024

8-K filing: 22nd Century Group, Inc. entered into a securities purchase agreement with certain investors for the issuance and sale of prefunded warrants to purchase common stock and warrants to purchase common stock, with the offering expected to close on October 24, 2024. ($6.0M proceeds)

46M 0
Oct 15, 2024

8-K filing: 22nd Century Group, Inc. entered into a securities purchase agreement on October 11, 2024, for the issuance and sale of common stock and warrants, with investors purchasing approximately $2.1 million of shares and warrants, consisting of 14,266,666 shares of Common Stock and warrants to purchase 28,533,333 shares of common stock at $0.15 per share and accompanying warrant, with the offering expected to close on October 14, 2024. ($2.1M proceeds)

46M 0
Sep 30, 2024

8-K filing: 22nd Century Group, Inc. reports several actions to increase stockholders' equity, including the issuance of common stock in connection with debt extinguishment, sales, and conversions, to meet Nasdaq's minimum equity requirement. ($11.6M proceeds)

2.7M 8.6M
Sep 30, 2024

8-K filing: 22nd Century Group, Inc. entered into a securities purchase agreement on September 27, 2024, for the issuance and sale of shares of common stock and warrants, and commenced a warrant inducement offering on September 29, 2024, with the holders of outstanding warrants. ($1.2M proceeds)

2.7M 8.6M
Sep 16, 2024

S-3 filing: This is an S-3 filing for the resale of up to 1,399,776 shares of common stock by selling stockholders.

2.7M 8.6M
Sep 13, 2024

8-K filing: 22nd Century Group, Inc. entered into subscription agreements to issue and sell 6,100,000 shares of Common Stock at $0.57 per share for gross proceeds of $3.48 million and also entered into a warrant purchase agreement for the private placement of 12,200,000 warrants at $0.00001 per warrant with an exercise price of $1.00 per share. ($3.48M proceeds)

2.7M 7.2M
Aug 28, 2024

8-K filing: 22nd Century Group, Inc. entered into a subscription agreement to issue and sell 2,950,000 shares of common stock at $0.57 per share for gross proceeds of $1.68 million and also agreed to a private placement of 2,596,000 warrants at a price of $0.00001 per warrant, with an exercise price of $1.00 per share. ($0.0M proceeds)

2.7M 7.2M
Aug 16, 2024

8-K filing: 22nd Century Group, Inc. entered into a subscription agreement to issue and sell 460,000 shares of Common Stock at $0.57 per share for gross proceeds of $262,200. ($0.26M proceeds)

2.7M 7.2M
Aug 13, 2024

10-Q filing | 2.7M shares outstanding

2.7M 7.2M
May 15, 2024

10-Q filing | 2.7M shares outstanding

2.7M 7.2M
May 10, 2024

8-K filing: The Company exchanged $2,327,632 in principal, fees and expenses owed under the Debentures for 395,000 shares of common stock and 895,000 immediately exerciseable pre-funded warrants at an effective per share price of $1.69. ($2.18M proceeds)

3.5M 6.4M
May 01, 2024

S-3 filing: This S-3 filing relates to the resale of up to 9,140,970 shares of common stock by selling stockholders, including shares issuable upon exercise of warrants.

3.5M 6.4M
Apr 30, 2024

8-K filing: 22nd Century Group, Inc. settled debt with Omnia Capital LP for cash, shares of common stock, and warrants; settled indebtedness under commercial agreements for shares of common stock.

3.5M 0
Apr 09, 2024

8-K filing: The company closed a registered direct offering and private placement on April 9, 2024, selling shares of common stock and warrants for approximately $4.2 million in gross proceeds. ($8.4M proceeds)

3.5M 0
Apr 08, 2024

8-K filing: The company entered into a securities purchase agreement for a $4.2 million offering of shares and warrants, and also modified terms with JGB Partners to allow for debt conversion to common stock at $2.14 per share. ($4.2M proceeds)

3.5M 0
Apr 02, 2024
Stock Split

8-K filing: Stock split 1-for-16 | Outstanding: 43,525,862 → 3,482,653

3.5M 0
Mar 28, 2024

10-K filing | 43.5M shares outstanding

44M 0
Nov 29, 2023

8-K filing: 22nd Century Group, Inc. commenced a warrant inducement offering with holders of outstanding warrants, offering new warrants to purchase shares of common stock at a reduced exercise price, and entered into warrant inducement agreements with certain holders to purchase 13,032,182 shares of common stock at $0.215, resulting in gross proceeds of approximately $2.8 million for the company. ($2.8M proceeds)

14M 0
Nov 06, 2023

10-Q filing | 14.3M shares outstanding

14M 0
Oct 18, 2023

8-K filing: 22nd Century Group, Inc. entered into a securities purchase agreement to sell 7,600,000 shares of common stock, warrants to purchase 20,000,000 shares of common stock, and pre-funded warrants to purchase 2,400,000 shares of common stock in a registered public offering, expected to close on or about October 19, 2023. ($5.25M proceeds)

15M 0
Oct 16, 2023

8-K filing: 22nd Century Group amended its agreement with JGB Partners, LP, JGB Capital, LP and JGB Capital Offshore Ltd., waiving a revenue target default, reducing a future revenue target, releasing $7.5 million in escrow funds to reduce the debenture principal, assigning the Pledged Indebtedness for consideration to reduce the Put Price and debenture principal and approving an amendment to the Company's Articles of Incorporation to increase the number of authorized shares of common stock from 33,333,334 to 66,666,667. ($2.5M proceeds)

15M 0
Aug 14, 2023

10-Q filing | 14.9M shares outstanding

15M 0
Jul 24, 2023

8-K filing: 22nd Century Group, Inc. completed a registered direct offering, selling 4,373,219 shares of common stock and 8,746,438 warrants at $2.67 per unit, resulting in gross proceeds of approximately $11.7 million and net proceeds of $10.6 million after deducting fees. ($11.7M proceeds)

16M 0
Jul 07, 2023

8-K filing: 22nd Century Group, Inc. entered into a securities purchase agreement with investors for a registered direct offering, selling 778,634 shares of common stock and 1,557,268 warrants at $3.80 per unit, resulting in gross proceeds of approximately $3.0 million and net proceeds of approximately $2.6 million after deducting fees and expenses. ($5.92M proceeds)

16M 0
Jul 05, 2023
Stock Split

8-K filing: Stock split 1-for-15 | Outstanding: 215,784,000 → 15,860,668

16M 0
Jun 21, 2023

8-K filing: 22nd Century Group, Inc. entered into a securities purchase agreement for a registered direct offering, issuing 11,219,516 shares of common stock and warrants to purchase an equal number of shares at $0.47 per unit, resulting in gross proceeds of approximately $5.3 million before fees. Additionally, the company increased its authorized shares of common stock from 300,000,000 to 500,000,000. ($5.3M proceeds)

220M 0
May 09, 2023

10-Q filing | 215.8M shares outstanding

220M 0
Apr 24, 2023

S-3/A filing: This prospectus relates to the resale of up to 5,675,000 shares of common stock issuable upon exercise of warrants.

220M 0
Apr 11, 2023

S-3 filing: This prospectus relates to the resale of up to 5,675,000 shares of common stock issuable upon exercise of warrants by selling stockholders.

220M 0
Apr 05, 2023

8-K filing: 22nd Century Group, Inc. issued five million shares of unregistered common stock to Cookies Creative Consulting & Promotions, Inc. as part of a License and Distribution Agreement.

220M 0
Mar 10, 2023

S-3 filing: 22nd Century Group, Inc. is filing an S-3 to offer and sell up to $250 million of debt securities, common stock, preferred stock, warrants, subscription rights, securities purchase contracts, and units from time to time, in one or more offerings.

220M 0
Mar 09, 2023

10-K filing | 215.2M shares outstanding

220M 0
Mar 03, 2023

8-K filing: The Company entered into a Securities Purchase Agreement to sell debentures and warrants, and issued warrants to Omnia Ventures in connection with a subordinated promissory note.

160M 13M
Nov 08, 2022

10-Q filing | 162.9M shares outstanding

160M 13M
Sep 02, 2022

S-3 filing: This S-3 filing relates to the offer and sale of up to 26,032,708 shares of common stock by selling stockholders, including shares issuable upon the exercise of outstanding warrants.

160M 13M
Aug 09, 2022

10-Q filing | 162.9M shares outstanding

160M 0
Jul 25, 2022

8-K filing: 22nd Century Group, Inc. closed a registered direct offering on July 25, 2022, selling 17,073,175 shares of common stock at $2.05 per share, and issued warrants to purchase up to 17,073,175 shares of common stock at an exercise price of $2.05 per share in a concurrent private placement. ($35.0M proceeds)

160M 0
May 05, 2022

10-Q filing | 163.2M shares outstanding

160M 0
Mar 01, 2022

10-K filing | 156.2M shares outstanding

160M 0
Nov 04, 2021

10-Q filing | 139.1M shares outstanding

140M 11M
Aug 05, 2021

10-Q filing | 139.1M shares outstanding

140M 11M
Jul 02, 2021

8-K filing: 22nd Century Group, Inc. entered into a Promissory Note Exchange Agreement with Panacea Life Sciences, Inc. and a Securities Exchange Agreement with PLS, Exactus, Inc., converting Series B Preferred Stock in PLS into 91,016,026 shares of restricted common stock in Exactus and restructuring existing debt in PLS.

140M 11M
Jun 07, 2021

8-K filing: 22nd Century Group, Inc. entered into a placement agent agreement with Cowen and Company, LLC and a securities purchase agreement with an investor for a registered direct offering of 10,000,000 shares of common stock at $4.00 per share, resulting in gross proceeds of $40 million. ($40.0M proceeds)

140M 11M
May 06, 2021

10-Q filing | 139.1M shares outstanding

140M 11M
Mar 11, 2021

10-K filing | 139.1M shares outstanding

140M 11M
Nov 05, 2020

10-Q filing | 138.4M shares outstanding

140M 12M
Aug 06, 2020

10-Q filing | 138.4M shares outstanding

140M 12M
Jul 21, 2020

S-3 filing: This is an S-3 filing for a shelf offering of debt securities, common stock, preferred stock, warrants, subscription rights, securities purchase contracts and units.

140M 11M
May 07, 2020

10-Q filing | 138.9M shares outstanding

140M 0
Mar 11, 2020

10-K filing | 138.9M shares outstanding

140M 0
Weekly Research

Get Weekly Super Stonk Alerts

Never miss a squeeze opportunity. Get our weekly analysis of high short interest stocks, AI-discovered gems, and dilution warnings delivered to your inbox.

No spam Unsubscribe anytime