11-Hydroxyhexahydrocannabinol

11-Hydroxyhexahydrocannabinol (11-OH-9β-HHC, alternatively numbered as 7-OH-HHC) is a minor active metabolite of tetrahydrocannabinol, and also a metabolite of the trace cannabinoid hexahydrocannabinol.[1]

11-Hydroxyhexahydrocannabinol
Identifiers
IUPAC name
  • (6aR,9R,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H32O3
Molar mass332.484 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCC1=CC(=C2[C@@H]3C[C@@H](CC[C@H]3C(OC2=C1)(C)C)CO)O
InChI
  • InChI=1S/C21H32O3/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/h11-12,15-17,22-23H,4-10,13H2,1-3H3/t15-,16-,17-/m1/s1
  • Key:LXSFNMQURHTPIT-BRWVUGGUSA-N

11-OH-9β-HHC is the structurally related methylene homologue of 11-Nor-9β-hydroxyhexahydrocannabinol also known as 9-Nor-9β-hydroxyhexahydrocannabinol.[2][3]

The structurally related synthetic dimethylheptyl analog of 11-OH-9β-HHC is known as HU-243. The only difference between HU-243 and 11-OH-9β-HHC is that HU-243 features a di (2) methyl groups on its tail chain that has been extended from pentyl (5 carbon atoms)) to heptyl (7 carbon atoms) which significantly increases its binding affinity to the CB1 and CB2 receptors.[4]

See also

References
  1. Järbe TU, Hiltunen AJ, Lander N, Mechoulam R (August 1986). "Cannabimimetic activity (delta 1-THC cue) of cannabidiol monomethyl ether and two stereoisomeric hexahydrocannabinols in rats and pigeons". Pharmacology, Biochemistry, and Behavior. 25 (2): 393–9. doi:10.1016/0091-3057(86)90015-8. PMID 3020594. S2CID 28373651.
  2. "9-Hydroxy-9-norhexahydrocannabinol".
  3. "7-Hydroxyhexahydrocannabinol".
  4. Devane WA, Breuer A, Sheskin T, Järbe TU, Eisen MS, Mechoulam R (May 1992). "A novel probe for the cannabinoid receptor". Journal of Medicinal Chemistry. 35 (11): 2065–9. doi:10.1021/jm00089a018. PMID 1317925.


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