X0306 4 2018-03-06 0 0001347858 22nd Century Group, Inc. XXII 0001508753 SICIGNANO HENRY III C/O 22ND CENTURY GROUP, INC. 8560 MAIN STREET WILLIAMSVILLE NY 14221 1 1 0 0 President and CEO Common Stock 2509422 D Common Stock 20000 I Custodian for Minor Child Common Stock 20000 I IRA Common Stock 2542347 I Manager Stock Option (Right to Buy) 2.76 2018-03-06 4 A 0 279553 2.76 A 2028-03-06 Common Stock 279553 279553 D Stock Option (Right to Buy) 0.69 2012-05-18 2022-05-18 Common Stock 100000 100000 D Stock Option (Right to Buy) 0.96 2016-02-16 2025-02-16 Common Stock 350000 350000 D Stock Option (Right to Buy) 0.95 2026-03-04 Common Stock 425532 425532 D Sock Option (Right to Buy) 1.39 2027-05-24 Common Stock 333000 333000 D Shares are owned by Henry Sicignano III Group, LLC. Stock option grant which vests one-third on March 6, 2019, March 6, 2020 and March 6, 2021. Stock option grant which vests one-third on each of April 1, 2018, April 1, 2019 and April 1, 2020. Stock option grant which vests one-third on each of March 4, 2017, March 4, 2018 and March 4, 2019. /s/ John J. Wolfel, Attorney-in-Fact for Henry Sicignano, III 2018-04-03