Tetrahydrocannabinols
Title: Tetrahydrocannabinols
Literature References: Psychoactive constituents of cannabis, q.v. (Cannabis sativa L. Cannabinaceae). The (-)-trans-D9 isomer (D9-THC) is the principal active constituent; the (-)-trans-D8 isomer (D8-THC), although physiologically active, is present to a lesser extent. D9 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 D9-THC: Y. Gaoni, R. Mechoulam, ibid. 86, 1646 (1964). Isoln of D8-THC: R. L. Hively et al., ibid. 88, 1832 (1966). Abs config of (-)-trans-D9 isomer: R. Mechoulam, Y. Gaoni, Tetrahedron Lett. 1967, 1109. Stereospecific synthesis of D8- and D9-THC: R. Mechoulam et al., J. Am. Chem. Soc. 89, 4552 (1967); of D9-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 D9-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).
 
Derivative Type: (-)-trans-D9-Form
CAS Registry Number: 1972-08-3
Additional Names: (6aR,10aR)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol; (-)-D1-3,4-trans-tetrahydrocannabinol; D9-THC; D1-THC; dronabinol
Manufacturers' Codes: QCD-84924
Trademarks: Marinol (Unimed)
Molecular Formula: C21H30O2
Molecular Weight: 314.46
Percent Composition: C 80.21%, H 9.62%, O 10.18%
Properties: Light yellow resinous oil; hardens upon refrigeration. bp0.02 200°. [a]D20 -150.5° (c = 0.53 in CHCl3). pKa 10.6. uv max (ethanol): 283, 276 nm (log e 3.21, 3.20). Essentially insol in water. LD50 (sesame oil emulsion) in male rats (mg/kg): 800 orally; 35.5. i.v.; 672 i.p. (Rosenkranz).
Boiling point: bp0.02 200°
Optical Rotation: [a]D20 -150.5° (c = 0.53 in CHCl3)
Absorption maximum: pKa 10.6. uv max (ethanol): 283, 276 nm (log e 3.21, 3.20)
Toxicity data: LD50 (sesame oil emulsion) in male rats (mg/kg): 800 orally; 35.5. i.v.; 672 i.p. (Rosenkranz)
 
Derivative Type: (-)-trans-D8-Form
CAS Registry Number: 5957-75-5
Additional Names: (-)-D6-3,4-trans-tetrahydrocannabinol; D8-THC; D6-THC
Properties: bp0.001 200°. [a]D18 -264° (c = 0.11 in ethanol). uv max (ethanol): 282, 275 nm (log e 3.22, 3.22); shoulder at 230 nm (log e 4.07). LD50 i.v. in mice: 27.5 mg/kg (Yoshimura).
Boiling point: bp0.001 200°
Optical Rotation: [a]D18 -264° (c = 0.11 in ethanol)
Absorption maximum: uv max (ethanol): 282, 275 nm (log e 3.22, 3.22); shoulder at 230 nm (log e 4.07)
Toxicity data: LD50 i.v. in mice: 27.5 mg/kg (Yoshimura)
 
NOTE: This is a controlled substance (hallucinogen): 21 CFR, 1308.11.
Therap-Cat: Antiemetic; appetite stimulant.
Keywords: Antiemetic.

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