11-Hydroxy-Δ8-THC

Metabolite of delta-8-THC {{DISPLAYTITLE:11-Hydroxy-Δ8-THC}} the isomer of this chemical inherited from Δ9-tetrahydrocannabinol 11-Hydroxy-THC January 2023 vanc 11-Hydroxy-Δ8-THC (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol 11-OH-D8-THC_structure.png skin-invert-image 220 28646-40-4 changed EPA None 185651 161395 7-OH-Δ6-THC GM4TR07BPX 21 30 3 CCCCCC1=CC(=C2[C@@H]3CC(=CC[C@H]3C(OC2=C1)(C)C)CO)O 1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h8,11-12,16-17,22-23H,4-7,9-10,13H2,1-3H3/t16-,17-/m1/s1 LOUSQMWLMDHRIK-IAGOWNOFSA-N Cannabinoid 11-Hydroxy-Δ8-tetrahydrocannabinol (11-hydroxy-Δ8-THC, alternatively numbered as 7-hydroxy-Δ6-THC) is an active metabolite of Δ8-THC, a psychoactive cannabinoid found in small amounts in Cannabis. It is an isomer of 11-OH-Δ9-THC, and is produced via the same metabolic pathway. It was the first cannabinoid metabolite discovered in 1970. Mechoulam R, Hanus L A historical overview of chemical research on cannabinoids Chemistry and Physics of Lipids 108 1–2 1–13 November 2000 11106779 10.1016/s0009-3084(00)00184-5 It retains psychoactive effects in animal studies with higher potency than Δ8-THC but lower potency than 11-OH-Δ9-THC. With widespread legal use of semi-synthetic Δ8-THC in certain jurisdictions where Δ9-THC remains illegal, 11-OH-Δ8-THC is now an important metabolite for distinguishing between use of hemp-derived Δ8-THC and natural Δ9-THC. Watanabe K, Yamamoto I, Oguri K, Yoshimura H Identification and determination of 11-oxo-delta8-tetrahydrocannabinol as an intermediate metabolite of delta8-tetrahydrocannabinol in the mouse brain and liver Journal of Pharmacobio-Dynamics 3 12 686–91 December 1980 6268770 10.1248/bpb1978.3.686 free Watanabe K, Yamamoto I, Oguri K, Yoshimura H Metabolic disposition of delta 8-tetrahydrocannabinol and its active metabolites, 11-hydroxy-delta 8-tetrahydrocannabinol and 11-oxo-delta 8-tetrahydrocannabinol, in mice Drug Metabolism and Disposition 1981 9 3 261–4 10.1016/S0090-9556(25)06140-9 6113937 Järbe TU, Mathis DA Discriminative stimulus functions of cannabinoids/cannabimimetics Drug Discrimination: Applications to Drug Abuse Research NIDA Research Monograph 116 75–99 1991 1369683 Yamamoto I, Kimura T, Kamei A, Yoshida H, Watanabe K, Ho IK, Yoshimura H Competitive inhibition of delta8-tetrahydrocannabinol and its active metabolites for cannabinoid receptor binding Biological & Pharmaceutical Bulletin 21 4 408–10 April 1998 9586583 10.1248/bpb.21.408 free Chan-Hosokawa A, Nguyen L, Lattanzio N, Adams WR Emergence of Delta-8 Tetrahydrocannabinol (THC) in DUID Investigation Casework: Method Development, Validation and Application Journal of Analytical Toxicology 46 1 March 2021 1–9 33754645 10.1093/jat/bkab029 free See also 11-Hydroxy-THC 11-Hydroxyhexahydrocannabinol 3'-Hydroxy-THC 7-Hydroxycannabidiol 8,11-Dihydroxytetrahydrocannabinol 9-OH-HHC 11-OH-HHC 11-OH-CBN 11-Nor-9-carboxy-THC Delta-6-Cannabidiol Delta-10-Tetrahydrocannabinol HU-210 Delta-11-Tetrahydrocannabinol References Category:Cannabinoids Category:Benzochromenes Category:Recreational drug metabolites Category:Hydroxyarenes Category:Primary alcohols