Description and references

Psychoactive constituents of cannabis, q.v. (Cannabis sativa L. Cannabinaceae). The (-)-trans-Δ⁹ isomer (Δ⁹-THC) is the principal active constituent; the (-)-trans-Δ⁸ isomer (Δ⁸-THC), although physiologically active, is present to a lesser extent. Δ⁹ analogs with shorter alkyl side chains have also been identified. Isoln from cannabis resin: H. J. Wollner et al., J. Am. Chem. Soc. 64, 26 (1942). Isoln and structure of Δ⁹-THC: Y. Gaoni, R. Mechoulam, ibid. 86, 1646 (1964). Isoln of Δ⁸-THC: R. L. Hively et al., ibid. 88, 1832 (1966). Abs config of (-)-trans-Δ⁹ isomer: R. Mechoulam, Y. Gaoni, Tetrahedron Lett. 1967, 1109. Stereospecific synthesis of Δ⁸- and Δ⁹-THC: R. Mechoulam et al., J. Am. Chem. Soc. 89, 4552 (1967); of Δ⁹-THC: R. K. Razden et al., ibid. 96, 5860 (1974); eidem, Experientia 31, 16 (1975). IR, NMR, MS data: T. Petrzilka, C. Sikemeier, Helv. Chim. Acta 50, 1416, 2111 (1967). Toxicity studies: H. Rosenkranz et al., Toxicol. Appl. Pharmacol. 28, 18 (1974); H. Yoshimura et al., J. Med. Chem. 21, 1079 (1978). Clinical experience with Δ⁹-THC in chemotherapy induced nausea and vomiting: D. S. Poster et al., J. Am. Med. Assoc. 245, 2047 (1981); as appetite stimulant in AIDS-associated anorexia: J. E. Beal et al., J. Pain Symptom Manage. 14, 7 (1997). Chromatographic determn in cannabis products: L. Vollner et al., Regul. Toxicol. Pharmacol. 6, 348-358 (1986). GC/MS determn in hair: M. J. Baptista et al., Forensic Sci. Int. 128, 66 (2002). Review of pharmacology: W. L. Dewey, Pharmacol. Rev. 38, 151-178 (1986); of pharmacokinetics and metabolism: F. Grotenhermen, Clin. Pharmacokinet. 42, 327-360 (2003).

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