8,11-Dihydroxytetrahydrocannabinol

8,11-Dihydroxytetrahydrocannabinol (8β,11-diOH-Δ⁹-THC) is an active metaboliteofTHC, the main active component of cannabis. The 8β enantiomer retains psychoactive effects in animal studies with only slightly lower potency than THC, while the 8α enantiomer is much weaker. Both enantiomers have a shorter half-life in the body than 11-hydroxy-THC, making 8,11-dihydroxy-THC potentially useful for drug testing to distinguish between recent cannabis use and use longer in the past.^[1]^[2]^[3]

8,11-Dihydroxytetrahydrocannabinol
Identifiers

IUPAC name (6aR,8R,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-1,8-diol
CAS Number	36913-21-0^N[EPA]
PubChem CID	101993955
ChemSpider	130500
CompTox Dashboard (EPA)	DTXSID80190397
Chemical and physical data
Formula	C₂₁H₃₀O₄
Molar mass	346.467 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCc1cc2OC(C)(C)[C@@H]3C[C@@H](O)C(=C[C@H]3c2c(O)c1)CO
InChI InChI=1S/C21H30O4/c1-4-5-6-7-13-8-18(24)20-15-10-14(12-22)17(23)11-16(15)21(2,3)25-19(20)9-13/h8-10,15-17,22-24H,4-7,11-12H2,1-3H3/t15-,16-,17-/m1/s1 Key:XTDYIISRNODHHT-BRWVUGGUSA-N

References

^ Pitt CG, Fowler MS, Sathe S, Srivastava SC, Williams DL (June 1975). "Synthesis of metabolites of delta-9-tetrahydrocannabinol". Journal of the American Chemical Society. 97 (13): 3798–3802. doi:10.1021/ja00846a040. PMID 1141589.

^ 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.

^ Gasse A, Pfeiffer H, Köhler H, Schürenkamp J (January 2018). "8β-OH-THC and 8β,11-diOH-THC-minor metabolites with major informative value?". International Journal of Legal Medicine. 132 (1): 157–164. doi:10.1007/s00414-017-1692-5. PMID 28983686. S2CID 19208736.

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8,11-Dihydroxytetrahydrocannabinol

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