11-Hydroxy-THC

11-Hydroxy-THC
11-Hydroxy-THC molecule
Identifiers
IUPAC name
  • (6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.164.583
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Chemical and physical data
FormulaC21H30O3
Molar mass330.468 g·mol−1
3D model (JSmol)
SMILES
  • Oc2cc(cc1OC(C3CC/C(=C\C3c12)CO)(C)C)CCCCC
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/h10-12,16-17,22-23H,4-9,13H2,1-3H3 checkY
  • Key:YCBKSSAWEUDACY-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

11-Hydroxy-Δ9-tetrahydrocannabinol (11-OH-Δ9-THC, alternatively numbered as 7-OH-Δ1-THC), usually referred to as 11-hydroxy-THC, is the main active metabolite of tetrahydrocannabinol (THC), which is formed in the body after decarboxylated cannabis is consumed.[1][2]

Fresh cannabis contains tetrahydrocannabinolic acid (THCA), which is converted into THC after heating and then metabolized by the body into 11-hydroxy-THC and then into 11-nor-9-carboxy-THC;[2] both compounds can be glucuronidated and mainly excreted into urine. Both compounds, along with THC, are assayed in blood tests.[1]

11-hydroxy-THC has a comparable psychoactive effect to THC, but with a faster onset of effect.[3]

See also

References

  1. 1 2 Kraemer T, Paul LD (August 2007). "Bioanalytical procedures for determination of drugs of abuse in blood". Analytical and Bioanalytical Chemistry. 388 (7): 1415–35. doi:10.1007/s00216-007-1271-6. PMID 17468860. S2CID 32917584.
  2. 1 2 Huestis MA (2005). "Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol". Handbook of Experimental Pharmacology. 168 (168): 657–90. doi:10.1007/3-540-26573-2_23. ISBN 3-540-22565-X. PMID 16596792.
  3. ↑ Lemberger, L.; Martz, R.; Rodda, B.; Forney, R.; Rowe, H. (1973). "Comparative Pharmacology of Δ9-Tetrahydrocannabinol and its Metabolite, 11-OH-Δ9-Tetrahydrocannabinol". The Journal of Clinical Investigation. 52 (10): 2411–2417. doi:10.1172/JCI107431. PMC 302499. PMID 4729039.
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