9-nor-9β-Hydroxyhexahydrocannabinol

9-nor-9β-Hydroxyhexahydrocannabinol

Systematic (IUPAC) name
6,6-Dimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromene-1,9-diol
Identifiers
CAS Number	52171-85-4
PubChem	CID: 6452587
Chemical data
Formula	C20H30O3
Molecular mass	318.449 g/mol
SMILES OC3CCC1C(C3)c2c(O)cc(CCCCC)cc2OC1(C)C

9-nor-9β-Hydroxyhexahydrocannabinol (HHC), is a synthetic cannabinoid derivative which resulted from early modifications to the structure of THC, in a search for the simplest compound that could still fulfil the binding requirements to produce cannabis-like activity. HHC is active in its own right with similar potency to THC, but further simplification and variation of this parent structure lead to more potent, yet structurally simpler derivatives such as CP 47,497 and CP 55,940, which after several steps of modification have become quite structurally distinct from THC, while HHC on the other hand is still substantially similar in structure to THC.

The discovery of this simplified class of cannabinoid derivatives was highly significant in terms of the widespread use of CP 55,940 for early scientific research into the cannabinoid receptors, as well as later work using more complex compounds such as CP 55,244 to map the CB₁ binding site in more detail, but aside from these specific applications, these compounds attracted little attention and no compounds from this series were developed for medical use despite favourable safety profiles in animal studies. Unexpectedly, some 25 years later, these compounds came back into prominence when an obscure derivative (C8)-CP 47,497 was found to have been sold as the active ingredient in the "herbal" cannabis substitute product Spice, which ironically has led to a resurgence of interest into laboratory-conducted scientific research of this family of drugs.

See also

• AM-2389
• HU-243