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11-Hydroxy-THC: Wikis

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11-Hydroxy-THC
Systematic (IUPAC) name
(6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-pentyl- 6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
Identifiers
CAS number 36557-05-8
ATC code  ?
PubChem 37482
ChemSpider 34385
Chemical data
Formula C 21H30O3  
Mol. mass 330.461 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

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] 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-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

  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. 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 (06): 714–9. PMID 1204277.  
  4. ^ Lemberger L, Martz R, Rodda B, Forney R, Rowe H. Comparative pharmacology of Delta9-tetrahydrocannabinol and its metabolite, 11-OH-Delta9-tetrahydrocannabinol. Journal of Clinical Investigation. 1973 Oct;52(10):2411-7. PMID 4729039
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