8,11-Dihydroxytetrahydrocannabinol

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
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H30O4
Molar mass346.467 g·mol−1
3D model (JSmol)
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

8,11-Dihydroxytetrahydrocannabinol (8β,11-diOH-Δ9-THC) is an active metabolite of THC, 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]

See also

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
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