11-Hydroxyhexahydrocannabinol

11-Hydroxyhexahydrocannabinol, an active metabolite of THC and HHC, undergoes hepatic metabolism to produce oxygenated derivatives, with C11-oxidation being a major pathway. This compound retains activity comparable to HHC but is rapidly metabolized into inactive 11-carboxylates. Structurally, it is the methylene homologue of 9-Nor-9β-hydroxyhexahydrocannabinol, and HU-243, a synthetic analog, has increased binding affinity for cannabinoid receptors.

Metabolism:

• 11-OH-9β-HHC is an active metabolite of THC and HHC.
• HHC undergoes hepatic metabolism by cytochrome p450 to oxygenated derivatives.
• C11-oxidation is a major pathway of THC and HHC metabolism.
• 11-OH-9β-HHC retains activity comparable to HHC.
• 11-OH-9β-HHC is rapidly metabolized to inactive 11-carboxylates.

Structural Related Compounds:

• 11-OH-9β-HHC is the methylene homologue of 9-Nor-9β-hydroxyhexahydrocannabinol.
• HU-243 is a synthetic analog of 11-OH-9β-HHC.
• HU-243 has a geminal-dimethylheptyl substitution.
• HU-243 has increased binding affinity for CB1 and CB2 receptors.
• 11-Nor-9β-hydroxyhexahydrocannabinol is also known as 9-Nor-9β-hydroxyhexahydrocannabinol.

Related Compounds:

• 9-Hydroxyhexahydrocannabinol.
• 9-Nor-9β-hydroxyhexahydrocannabinol.
• 11-Hydroxycannabinol.
• HU-210.
• 8-hydroxyhexahydrocannabinol.

References:

• Cannabimimetic activity of cannabidiol monomethyl ether and hexahydrocannabinols.
• Comparative in vivo metabolism of THC, CBD, and CBN.
• Evidence of 11-Hydroxy-hexahydrocannabinol as a novel human metabolite of THC.
• Metabolomics implications of Δ9-tetrahydrocannabinol.
• Human cannabinoid pharmacokinetics.

Additional Information:

• PubChem data on 9-Hydroxy-9-norhexahydrocannabinol.
• PubChem data on 7-Hydroxyhexahydrocannabinol.
• Novel probe for the cannabinoid receptor.
• Rapid elimination of Carboxy-THC in chronic cannabis users.

11-Hydroxyhexahydrocannabinol Data Sources