Planta Med 2008; 74 - P-20
DOI: 10.1055/s-2008-1075216

X-ray Crystal Structure of Δ9-THC-tosylate

W Gul 1, 2, P Carvalho 3, D Slade 2, M Avery 3, JR Duchek 5, DW Bab 5, DJ Kimmich 5, MA ElSohly 1, 2, 4
  • 1ElSohly Laboratories, Inc., 5 Industrial Park Drive, Oxford, MS 38655, USA.
  • 2National Center for Natural Products Research,
  • 3Department of Medicinal Chemistry,
  • 4Department of Pharmaceutics, School of Pharmacy,The University of Mississippi, University, MS 38677, USA
  • 5Covidien, 3600 N, 2nd Street, St. Louis, MO, 63147, USA

Cannabis has had a long history of use (over 5,000 years) starting in Central and Northeast Asia, with current use spreading worldwide as a recreational drug or as a medicine, albeit unauthorized. Cannabis is very complex in its chemistry due to the vast number of its constituents and their possible interaction with one another. These compounds represent at least 18 different chemical classes, e.g. cannabinoids, non-cannabinoid phenols, mono- and sesquiterpenes, sugars, hydrocarbons, steroids, flavonoids, nitrogenous compounds and amino acids. The best-known and the most specific class of cannabis constituents is the C21 terpenophenolic cannabinoids, with tetrahydrocannabinol (Δ9-THC, 1) being the most psychologically active constituent [1]. Δ9-THC (1) is susceptible to air oxidation and rearrangement, making storage, either neat or in solution, problematic. Crystalline Δ9-THC-tosylate (2) [2], however, is stable and can be stored at room temperature without any degradation. The x-ray crystal structure of 2 is presented in this poster. References: [1] Mechoulam R, Gaoni Y (1967) Fortschritte der Chemie Organischer Naturstoffe 25: 175–213. [2] Duchek JR US Publication # 2006-0094774.