KM-233 is a
synthetic cannabinoid
Synthetic cannabinoids, or neocannabinoids, are a class of designer drug molecules that Binding affinity, bind to the same receptors to which cannabinoids (Tetrahydrocannabinol, THC, Cannabidiol, CBD and many others) in cannabis plants attach. Th ...
drug which is a
structural analog
A structural analog, also known as a chemical analog or simply an analog, is a chemical compound, compound having a chemical structure, structure similar to that of another compound, but differing from it in respect to a certain component.
It can ...
of Δ8-
tetrahydrocannabinol
Tetrahydrocannabinol (THC) is a cannabinoid found in cannabis. It 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) de ...
(THC), the less active but more stable
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
of the active component of ''
Cannabis
''Cannabis'' () is a genus of flowering plants in the family Cannabaceae that is widely accepted as being indigenous to and originating from the continent of Asia. However, the number of species is disputed, with as many as three species be ...
''. KM-233 differs from Δ8-THC by the
pentyl side chain
In organic chemistry and biochemistry, a side chain is a substituent, chemical group that is attached to a core part of the molecule called the "main chain" or backbone chain, backbone. The side chain is a hydrocarbon branching element of a mo ...
being replaced by a 1,1-dimethylbenzyl group. It has high binding affinity ''in vitro'' for both the
CB1 and
CB2 receptors, with a CB
2 affinity of 0.91 nM and 13-fold selectivity over the CB
1 receptor. In animal studies, it has been found to be a potential treatment for
glioma
A glioma is a type of primary tumor that starts in the glial cells of the brain or spinal cord. They are malignant but some are extremely slow to develop. Gliomas comprise about 30% of all brain and central nervous system tumors and 80% of ...
, a form of brain tumor. Many related analogues are known where the 1,1-dimethylbenzyl group is substituted or replaced by other groups, with a fairly well established
structure-activity relationship.
See also
*
AM-411
*
AMG-36
References
Hydroxyarenes
Cannabinoids
Benzochromenes
{{cannabinoid-stub