11-Hydroxy-Δ-8-THC

11-Hydroxy-Δ-8-THC
Identifiers
	IUPAC name (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol;
CAS Number	28646-40-4 [EPA];
PubChem CID	185651;
ChemSpider	161395;
UNII	GM4TR07BPX;
CompTox Dashboard (EPA)	DTXSID101016542 ;
Chemical and physical data
Formula	C21H30O3
Molar mass	330.468 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC1=CC(=C2[C@@H]3CC(=CC[C@H]3C(OC2=C1)(C)C)CO)O;
	InChI 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]

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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[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.

[pmid1369683-4] 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.

[Chan-Hosokawa_2021-6] 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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Identifiers

IUPAC name (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number	28646-40-4^N[EPA]
PubChem CID	185651
ChemSpider	161395
UNII	GM4TR07BPX
CompTox Dashboard (EPA)	DTXSID101016542
Chemical and physical data
Formula	C₂₁H₃₀O₃
Molar mass	330.468 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCC1=CC(=C2[C@@H]3CC(=CC[C@H]3C(OC2=C1)(C)C)CO)O
InChI 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-THC

See also

References