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11-Hydroxyhexahydrocannabinol (11-OH-9α-HHC and 11-OH-9β-HHC, or alternatively 7-OH-HHC under the benzopyran numbering system) is an active metabolite of tetrahydrocannabinol (THC) and the major metabolite of the trace cannabinoid hexahydrocannabinol (HHC).
In a pathway that parallels the metabolism of the THC family of cannabinoids, following ingestion HHC undergoes hepatic metabolism by 
Like other 11-OH cannabinoid metabolites, 11-OH-9β-HHC retains activity comparable to HHC itself while the 9α-isomer is significantly less active. However, upon formation it is rapidly metabolized further to the inactive 11-carboxylates, producing a shortened half-life within the body and lowering its bioavailability considerably through first-pass metabolism.
The 11-OH-9β-HHC isomer is the structurally related methylene homologue of 11-Nor-9β-hydroxyhexahydrocannabinol also known as 9-Nor-9β-hydroxyhexahydrocannabinol.
The synthetic dimethylheptyl analog of 11-OH-9β-HHC is known as HU-243. In HU-243, the ''n-''pentyl side chain of 11-OH-9β-HHC is replaced with a ''geminal-''dimethylheptyl group which significantly increases its binding affinity to the CB1 and CB2 receptors.
cytochrome p450
Cytochromes P450 (CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are ...
(predominantly the CYP3A4 isozyme, with some contribution from CYP2C9 and CYP2C19) to a multitude of oxygenated derivatives, including 8-OH-HHC and 11-OH-HHC. C11-oxidation is the major pathway of THC and HHC metabolism.
Like other 11-OH cannabinoid metabolites, 11-OH-9β-HHC retains activity comparable to HHC itself while the 9α-isomer is significantly less active. However, upon formation it is rapidly metabolized further to the inactive 11-carboxylates, producing a shortened half-life within the body and lowering its bioavailability considerably through first-pass metabolism.
The 11-OH-9β-HHC isomer is the structurally related methylene homologue of 11-Nor-9β-hydroxyhexahydrocannabinol also known as 9-Nor-9β-hydroxyhexahydrocannabinol.
The synthetic dimethylheptyl analog of 11-OH-9β-HHC is known as HU-243. In HU-243, the ''n-''pentyl side chain of 11-OH-9β-HHC is replaced with a ''geminal-''dimethylheptyl group which significantly increases its binding affinity to the CB1 and CB2 receptors.
See also
* 9-Hydroxyhexahydrocannabinol * 9-Nor-9β-hydroxyhexahydrocannabinol * 11-Hydroxycannabinol * HU-210 * 8-hydroxyhexahydrocannabinolReferences
Benzochromenes Cannabinoids {{cannabinoid-stub