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Chemical compound
9-Nor-9β-hydroxyhexahydrocannabinol
6,6-Dimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c ]chromene-1,9-diol
CAS Number
PubChem
CID
ChemSpider
UNII
CompTox Dashboard (
EPA )
Formula C 20 H 30 O 3
Molar mass 318.457 g·mol−1 3D model (
JSmol )
CCCCCc1cc(c2c(c1)OC([C@H]3[C@H]2C[C@@H](CC3)O)(C)C)O
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]
See also
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 .
Phytocannabinoids (
comparison )
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