11-Hydroxy-Delta-8-THC
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Formula | C21H30O3 |
Molar mass | 330.468 g·mol−1 |
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11-Hydroxy-Delta-8-tetrahydrocannabinol (11-OH-Δ8-THC, alternatively numbered as 7-OH-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.[1]
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 legal Δ8-THC and illegal Δ9-THC.[2][3][4][5][6]
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
- ^ Mechoulam R, Hanus L (November 2000). "A historical overview of chemical research on cannabinoids". Chemistry and Physics of Lipids. 108 (1–2): 1–13. doi:10.1016/s0009-3084(00)00184-5. PMID 11106779.
- ^ Watanabe K, Yamamoto I, Oguri K, Yoshimura H (December 1980). "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. doi:10.1248/bpb1978.3.686. PMID 6268770.
- ^ Watanabe K, Yamamoto I, Oguri K, Yoshimura H (1981). "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. 9 (3): 261–4. PMID 6113937.
- ^ Järbe TU, Mathis DA (1991). "Discriminative stimulus functions of cannabinoids/cannabimimetics". Drug Discrimination: Applications to Drug Abuse Research. NIDA Research Monograph. pp. 75–99. PMID 1369683.
- ^ Yamamoto I, Kimura T, Kamei A, Yoshida H, Watanabe K, Ho IK, Yoshimura H (April 1998). "Competitive inhibition of delta8-tetrahydrocannabinol and its active metabolites for cannabinoid receptor binding". Biological & Pharmaceutical Bulletin. 21 (4): 408–10. doi:10.1248/bpb.21.408. PMID 9586583.
- ^ Chan-Hosokawa A, Nguyen L, Lattanzio N, Adams WR (March 2021). "Emergence of Delta-8 Tetrahydrocannabinol (THC) in DUID Investigation Casework: Method Development, Validation and Application". Journal of Analytical Toxicology. 46 (1): 1–9. doi:10.1093/jat/bkab029. PMID 33754645.
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(comparison)
Cannabibutols |
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Cannabicyclols |
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Cannabidiols | |
Cannabielsoins |
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Cannabigerols | |
Cannabiphorols |
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Cannabinols | |
Cannabitriols |
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Cannabivarins |
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Delta-8-tetrahydrocannabinols |
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Delta-9-tetrahydrocannabinols | |
Delta-10-Tetrahydrocannabinols | |
Miscellaneous cannabinoids |
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Active metabolites |
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- O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
cannabinoid
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enhancers
(inactivation inhibitors)
- 4-Nonylphenylboronic acid
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- Arvanil
- BIA 10-2474
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- SR-144,528
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- TM-38837
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- See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
- List of: AM cannabinoids
- JWH cannabinoids
- Designer drugs § Synthetic cannabimimetics
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