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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 
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
tetrahydrocannabinol
Tetrahydrocannabinol (THC) is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term ''THC'' ...
(THC) and the major metabolite of the trace cannabinoid hexahydrocannabinol
Hexahydrocannabinol (HHC) is a hydrogenated derivative of tetrahydrocannabinol. It is a naturally occurring phytocannabinoid that has rarely been identified as a trace component in ''Cannabis sativa'', but can also be produced synthetically by hy ...
(HHC).
In a pathway that parallels the metabolism of the THC family of cannabinoids, following ingestion HHC undergoes hepatic metabolism by 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
9-Nor-9β-hydroxyhexahydrocannabinol (9-Nor-9beta-HHC, sometimes incorrectly confused with 11-nor-9β-hydroxyhexahydrocannabinol),is a cannabinoid first discovered from early modifications to the structure of THC, in a search for the simplest com ...
.
The synthetic dimethylheptyl analog of 11-OH-9β-HHC is known as HU-243
HU-243 (AM-4056) is a synthetic cannabinoid drug that is a single enantiomer of the hydrogenated derivative of the commonly used reference agonist HU-210. It is a methylene homologue of canbisol. It is a potent agonist at both the CB1 and ...
. 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-Hydroxyhexahydrocannabinol (9-OH-HHC) is a semi-synthetic derivative of tetrahydrocannabinol. It is formed as an impurity in the synthesis of Delta-8-THC, and retains activity in animal studies though with only around 1/10 the potency of Δ9-TH ...
* 9-Nor-9β-hydroxyhexahydrocannabinol
9-Nor-9β-hydroxyhexahydrocannabinol (9-Nor-9beta-HHC, sometimes incorrectly confused with 11-nor-9β-hydroxyhexahydrocannabinol),is a cannabinoid first discovered from early modifications to the structure of THC, in a search for the simplest com ...
* 11-Hydroxycannabinol
11-Hydroxycannabinol (11-OH-CBN) is the main active metabolite of cannabinol (CBN), one of the active components of cannabis, and has also been isolated from cannabis itself. It is more potent than CBN itself, acting as an agonist of CB1 with a ...
* HU-210
HU-210 is a synthetic cannabinoid that was first chemical synthesis, synthesized in 1988 from (1R,5S)-myrtenol by a group led by Raphael Mechoulam at the Hebrew University. HU-210 is 100 to 800 times more potent than natural Tetrahydrocannabinol, ...
* 8-hydroxyhexahydrocannabinol
References
Benzochromenes Cannabinoids {{cannabinoid-stub