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JWH-176 is an analgesic drug which acts as a
cannabinoid receptor agonist
Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...
. Its binding affinity
In biochemistry and pharmacology, a ligand is a substance that forms a complex with a biomolecule to serve a biological purpose. The etymology stems from ''ligare'', which means 'to bind'. In protein-ligand binding, the ligand is usually a m ...
at the CB1 receptor is 26.0 nM, making it more potent than THC
Tetrahydrocannabinol (THC) 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) describes multiple isomers, the term ''THC' ...
itself, however JWH-176 is particularly notable in that it is a hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
containing no heteroatom
In chemistry, a heteroatom () is, strictly, any atom that is not carbon or hydrogen.
Organic chemistry
In practice, the term is usually used more specifically to indicate that non-carbon atoms have replaced carbon in the backbone of the molecula ...
s. This demonstrates that reasonably high-affinity cannabinoid
Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...
binding and agonist effects can be produced by compounds with no hydrogen bonding
In chemistry, a hydrogen bond (or H-bond) is a primarily electrostatic force of attraction between a hydrogen (H) atom which is covalently bound to a more electronegative "donor" atom or group (Dn), and another electronegative atom bearing a l ...
capacity at all, relying merely on Van der Waals and possibly hydrophobic interactions to bind to the receptor. It was discovered by, and named after, John W. Huffman.
Stereochemistry
JWH-176 is the (''E'')-stereoisomer of 1-( -pentylinden-1-ylidineethyl)naphthalene, whereas JWH-171 is the mixture of the (''E'')- and (''Z'')-isomers. :
Legal status
In the United States, CB1 receptor agonists of the 1-(1-naphthylmethylene)indene class such as JWH-176 and JWH-171 areSchedule I Controlled Substance
This is the list of Schedule I drugs as defined by the United States Controlled Substances Act. 21 CFRbr>1308.11(CSA Sched I) with changes through (Oct 18, 2012). Retrieved September 6, 2013. The following findings are required for drugs to be pla ...
s.
As of 23 December 2009, any compound structurally derived from 1–(1–naphthylmethyl)indene by substitution at the 3–position of the indene ring by an alkyl group is a Class B drug in the United Kingdom.
See also
* JWH-175References