11-Hydroxyhexahydrocannabinol

11-Hydroxyhexahydrocannabinol is an active metabolite of tetrahydrocannabinol and a metabolite of the trace cannabinoid hexahydrocannabinol.
In a pathway that parallels the metabolism of the THC family of cannabinoids, following ingestion HHC undergoes hepatic metabolism by cytochrome p450 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.
HU-243 is a synthetic analog of 11-OH-9β-HHC in which the natural n-pentyl side chain is replaced with a geminal-dimethylheptyl substitution. This significantly increases HU-243s binding affinity for the CB1 and CB2 receptors.