9-Nor-9β-hydroxyhexahydrocannabinol

9-Nor-9β-hydroxyhexahydrocannabinol
Identifiers
	IUPAC name 6,6-Dimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromene-1,9-diol;
CAS Number	52171-85-4 ;
PubChem CID	6452587;
ChemSpider	23232433;
UNII	NA3QQQ5D4S;
CompTox Dashboard (EPA)	DTXSID30966529 ;
Chemical and physical data
Formula	C20H30O3
Molar mass	318.457 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCc1cc(c2c(c1)OC([C@H]3[C@H]2C[C@@H](CC3)O)(C)C)O;
	InChI InChI=1S/C20H30O3/c1-4-5-6-7-13-10-17(22)19-15-12-14(21)8-9-16(15)20(2,3)23-18(19)11-13/h10-11,14-16,21-22H,4-9,12H2,1-3H3/t14-,15-,16-/m1/s1; Key:AAIHVZNCFQTVCA-BZUAXINKSA-N;

9-Nor-9β-hydroxyhexahydrocannabinol (9-nor-9beta-HHC; sometimes incorrectly confused with 11-nor-9β-hydroxyhexahydrocannabinol^[1]) is a cannabinoid first discovered from early modifications to the structure of THC, in a search for the simplest compound that could still fulfill the binding requirements to produce cannabis-like activity.^[2]^[3]

11-Hydroxyhexahydrocannabinol is the structurally related methylene homologue of 11-nor-9β-hydroxyhexahydrocannabinol that has been found as a minor active metabolite of tetrahydrocannabinol, and also a metabolite of the trace cannabinoid hexahydrocannabinol.^[4]

References

^ "9-Hydroxy-9-norhexahydrocannabinol".
^ Johnson MR, Althuis TH, Bindra JS, Harbert CA, Melvin LS, Milne GM (1980). Potent Analgetics Derived From 9-Nor-9β-Hydroxyhexahydrocannabinol. NIDA Research Monograph. Vol. 34. pp. 68−74.
^ Melvin LS, Johnson MR (1987). "Relationships of Tricyclic and Nonclassical Bicyclic Cannabinoids". In Rapaka RS, Makriyannis A (eds.). Structure-activity Relationships of the Cannabinoids. NIDA Research Monograph. Vol. 79. pp. 31–47.
^ 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.

[1] "9-Hydroxy-9-norhexahydrocannabinol".

[2] Johnson MR, Althuis TH, Bindra JS, Harbert CA, Melvin LS, Milne GM (1980). Potent Analgetics Derived From 9-Nor-9β-Hydroxyhexahydrocannabinol. NIDA Research Monograph. Vol. 34. pp. 68−74.

[3] Melvin LS, Johnson MR (1987). "Relationships of Tricyclic and Nonclassical Bicyclic Cannabinoids". In Rapaka RS, Makriyannis A (eds.). Structure-activity Relationships of the Cannabinoids. NIDA Research Monograph. Vol. 79. pp. 31–47.

[4] 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.

[1]

[2]

[3]

[4]

See also

References