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11-Hydroxy-Δ-8-THC

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For the isomer of this chemical inherited from Δ9-tetrahydrocannabinol, see 11-Hydroxy-THC.
11-Hydroxy-Δ-8-THC
Identifiers
  • (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H30O3
Molar mass330.468 g·mol−1
3D model (JSmol)
  • CCCCCC1=CC(=C2[C@@H]3CC(=CC[C@H]3C(OC2=C1)(C)C)CO)O
  • InChI=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
  • Key:LOUSQMWLMDHRIK-IAGOWNOFSA-N

11-Hydroxy-Δ-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 hemp-derived Δ8-THC and natural Δ9-THC.[2][3][4][5][6]

See also

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References

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  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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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