11-Hydroxy-THC

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
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	36557-05-8
ATC code	?
PubChem	CID 37482
ChemSpider	34385 Y
Chemical data
Formula	C21H30O3
Mol. mass	330.461 g/mol
SMILES	eMolecules & PubChem
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 Y Key:YCBKSSAWEUDACY-UHFFFAOYSA-N Y
Y (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-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 (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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=302499.