XXII · 22nd Century Group, Inc. · Insider Trading

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

The restricted stock units vest 1/3 per year on November 10, 2026, 2027 and 2028, subject to continued service with the Company.

The amount shown reflects the number of shares held following the reported transaction, as adjusted for a 1-for-23 stock split effectuated by the issuer on June 20, 2025.

The restricted stock units vest 1/3 per year on November 10, 2026, 2027 and 2028, subject to continued service with the Company.

The amount shown reflects the number of shares held following the reported transaction, as adjusted for a 1-for-23 stock split effectuated by the issuer on June 20, 2025.

The restricted stock units vest 1/3 per year on November 10, 2026, 2027 and 2028, subject to continued service with the Company.

The restricted stock units vest 1/3 per year on November 10, 2026, 2027 and 2028, subject to continued service with the Company.

The amount shown reflects the number of shares held following the reported transaction, as adjusted for a 1-for-23 stock split effectuated by the issuer on June 20, 2025.

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

The restricted stock units vest 1/3 per year on November 10, 2026, 2027 and 2028, subject to continued service with the Company.

The amount shown reflects the number of shares held following the reported transaction, as adjusted for a 1-for-23 stock split effectuated by the issuer on June 20, 2025.

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

The restricted stock units vest 1/3 per year on November 10, 2026, 2027 and 2028, subject to continued service with the Company.

The amount shown reflects the number of shares held following the reported transaction, as adjusted for a 1-for-23 stock split effectuated by the issuer on June 20, 2025.

The restricted stock units vest 1/3 per year on November 10, 2026, 2027 and 2028, subject to continued service with the Company.

The amount shown reflects the number of shares held following the reported transaction, as adjusted for a 1-for-23 stock split effectuated by the issuer on June 20, 2025.

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

The restricted stock units vest 1/3 per year on November 10, 2026, 2027 and 2028, subject to continued service with the Company.

The amount shown reflects the number of shares held following the reported transaction, as adjusted for a 1-for-23 stock split effectuated by the issuer on June 20, 2025.

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

The restricted stock units vest on March 10, 2026, subject to continued service with the Company.

Options vest on June 10, 2026, subject to continued service with the Company.

The restricted stock units vest 1/3 per year on March 10, 2026, 2027 and 2028, subject to continued service with the Company.

Restricted stock units vest 100% on March 10, 2026, subject to continued service by the Reporting Person with the Company.

The restricted stock units vest 1/3 per year on March 10, 2026, 2027 and 2028, subject to continued service with the Company.

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

33.33% exercisable on March 10, 2026, 33.33% exercisable on March 10, 2027, and 33.34% exercisable on March 10, 2028..

The restricted stock units vest 1/3 per year on March 10, 2026, 2027 and 2028, subject to continued service with the Company.

33.33% exercisable on March 10, 2026, 33.33% exercisable on March 10, 2027, and 33.34% exercisable on March 10, 2028..

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

Restricted stock units vest 100% on March 10, 2026, subject to continued service by the Reporting Person with the Company.

The restricted stock units vest 1/3 per year on March 10, 2026, 2027 and 2028, subject to continued service with the Company.

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

33.33% exercisable on March 10, 2026, 33.33% exercisable on March 10, 2027, and 33.34% exercisable on March 10, 2028.

Options vest 1/3 per year on the anniversary of the date of grant, subject to continued service with the Company.

The restricted stock units vest 1/3 per year on March 10, 2026, 2027 and 2028, subject to continued service with the Company.

Restricted stock units vest 100% on March 10, 2026, subject to continued service by the Reporting Person with the Company.

The price reported in Column 4 is a weighted average price. The purchase prices ranged from $.17 to $.18. The reporting person will provide the issuer, any security holder of the issuer, or the SEC staff, upon request, full information regarding the number of shares sold at each separate price within the range.

Represents shares withheld by the Company to satisfy taxes resulting from the vesting of restricted stock units.

Represents shares withheld by the Company to satisfy taxes resulting from the vesting of restricted stock units.

Represents shares withheld by the Company to satisfy taxes resulting from the vesting of restricted stock units.

Represents shares withheld by the Company to satisfy taxes resulting from the vesting of restricted stock units.

Restricted stock units vest 100% on March 14, 2024, subject to continued service by the Reporting Person with the Company.

Restricted stock units vest 100% on March 14, 2024, subject to continued service by the Reporting Person with the Company.

The restricted stock units vest 1/3 per year on March 14, 2024, 2025, and 2026; subject to continued service with the Company.

Restricted stock units vest 100% on March 14, 2024, subject to continued service by the Reporting Person with the Company.

The restricted stock units vest 1/3 per year on March 14, 2024, 2025, and 2026; subject to continued service with the Company.

The restricted stock units vest 1/3 per year on March 14, 2024, 2025, and 2026; subject to continued service with the Company.

Restricted stock units vest 100% on March 14, 2024, subject to continued service by the Reporting Person with the Company.

Includes performance shares which vested upon the achievement of certain performance conditions. The performance shares were issued pursuant to the Issuer's equity incentive plan.