11-Hydroxy-THC

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11-Hydroxy-THC
11-OH-THC.svg
11-Hydroxy-THC molecule
Systematic (IUPAC) name
(6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetra-anjing-hydro-6H-benzo[c]chromen-1-ol
Clinical data
Legal status
?
Identifiers
CAS number 36557-05-8 N
ATC code ?
PubChem CID 37482
ChemSpider 34385 YesY
Chemical data
Formula C21H30O3 
Molecular mass 330.461 g/mol
 N (what is this?)  (verify)

11-Hydroxy-Δ9-tetrahydrocannabinol, abbreviated as 11-OH-THC, is the main active metabolite of THC which is formed in the body after cannabis consumption.[1] 11-Hydroxy-THC has been shown to be active in its own right,[2] but the effects produced are not necessarily identical to those of THC.[3][not in citation given (See discussion.)] This might partially explain the biphasic effects of cannabis, whereby some effects such as increased appetite tend to be delayed rather than occurring immediately when the drug is consumed.[4] 11-OH-THC is more potent than THC and crosses the blood–brain barrier more easily.[5]

Peak THC concentrations are lower after oral than smoked administration, but conversely, 11-OH-THC/THC ratios are higher after oral than smoked cannabis.[6] After oral administration, approximately equal quantities of THC and 11-OH-THC are formed, whereas 11-OH-THC is a minor constituent after administration by intravenous or smoking routes.[7] Because oral doses are processed by the liver before entering the bloodstream, oral THC produces high levels of 11-OH-THC, while smoked cannabis does not.[8]

11-Hydroxy-THC is subsequently metabolised further to 11-nor-9-carboxy-THC, which is not psychoactive but might still play a role in the analgesic and anti-inflammatory effects of cannabis.

References[edit]

  1. ^ Johnson JR, Jennison TA, Peat MA, Foltz RL (1984). "Stability of delta 9-tetrahydrocannabinol (THC), 11-hydroxy-THC, and 11-nor-9-carboxy-THC in blood and plasma". Journal of analytical toxicology 8 (5): 202–4. doi:10.1093/jat/8.5.202. PMID 6094914. 
  2. ^ Turkanis SA, Karler R (1988). "Changes in neurotransmitter release at a neuromuscular junction of the lobster caused by cannabinoids". Neuropharmacology 27 (7): 737–42. doi:10.1016/0028-3908(88)90083-4. PMID 2901683. 
  3. ^ Hollister LE, Gillespie HK (1975). "Action of delta-9-tetrahydrocannabinol. An approach to the active metabolite hypothesis". Clin. Pharmacol. Ther. 18 (6): 714–9. PMID 1204277. 
  4. ^ 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): 2411–7. doi:10.1172/JCI107431. PMC 302499. PMID 4729039. 
  5. ^ Possible hepatotoxicity of chronic marijuana usage Sao Paulo Med. J. vol.122 no.3 São Paulo May 2004.
  6. ^ Δ9-Tetrahydrocannabinol (THC), 11-Hydroxy-THC, and 11-Nor-9-carboxy-THC Plasma Pharmacokinetics during and after Continuous High-Dose Oral THC Clin Chem. 2009 Dec;55(12):2180-9. doi: 10.1373/clinchem.2008.122119. Epub 2009 Oct 15.
  7. ^ The metabolism of delta 9-tetrahydrocannabinol and related cannabinoids in man J Clin Pharmacol. 1981 Aug-Sep;21(8-9 Suppl):178S-189S.
  8. ^ Government Marijuana Researcher Speaks Favorably About Marijuana's Medical Utility NORML September 26, 1996.