9-nor-9β-Hydroxyhexahydrocannabinol
Encyclopedia
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 receptor
s, 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.
Tetrahydrocannabinol
Tetrahydrocannabinol , also known as delta-9-tetrahydrocannabinol , Δ1-THC , or dronabinol, is the main chemical psychoactive substance found in the cannabis plant. It was first isolated in 1964. In pure form, it is a glassy solid when cold, and becomes viscous and sticky if warmed...
, 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
CP 47,497
CP 47,497 is a cannabinoid receptor agonist drug, developed by Pfizer in the 1980s. It has analgesic effects and is used in scientific research...
and CP 55,940
CP 55,940
CP 55,940 is a cannabinoid which mimics the effects of naturally occurring THC . CP 55,940 was created by Pfizer in 1974 but was never marketed. It is currently used to study the endocannabinoid system...
, 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 receptor
Cannabinoid receptor
The cannabinoid receptors are a class of cell membrane receptors under the G protein-coupled receptor superfamily. As is typical of G protein-coupled receptors, the cannabinoid receptors contain seven transmembrane spanning domains...
s, as well as later work using more complex compounds such as CP 55,244
CP 55,244
CP 55,244 is a compound which is a cannabinoid receptor agonist. It has analgesic effects and is used in scientific research. It is an extremely potent CB1 full agonist with a Ki of 0.21nM, making it more potent than the commonly used full agonist HU-210....
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
Spice (drug)
Synthetic cannabis is a psychoactive herbal and chemical product which, when consumed, mimics the effects of cannabis. It is best known by the brand names K2 and Spice, both of which have largely become genericized trademarks used to refer to any synthetic cannabis product...
, which ironically has led to a resurgence of interest into laboratory-conducted scientific research of this family of drugs.