11-Hydroxyhexahydrocannabinol

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	64663-39-4;
PubChem CID	127684;
ChemSpider	113271;
CompTox Dashboard (EPA)	DTXSID00983283 ;
Chemical and physical data
Formula	C21H32O3
Molar mass	332.484 g·mol−1
3D model (JSmol)	Interactive image;
	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-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-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]

References[]

^ 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.
^ "9-Hydroxy-9-norhexahydrocannabinol".
^ "7-Hydroxyhexahydrocannabinol".
^ 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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[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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[2]

[3]

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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	64663-39-4
PubChem CID	127684
ChemSpider	113271
CompTox Dashboard (EPA)	DTXSID00983283
Chemical and physical data
Formula	C₂₁H₃₂O₃
Molar mass	332.484 g·mol⁻¹
3D model (JSmol)	Interactive image
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-Hydroxyhexahydrocannabinol

See also[]

References[]