JWH-203 (1-pentyl-3-(2-chlorophenylacetyl)indole) is an

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

chemical from the phenylacetylindole family that acts as a

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 ...

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ag ...

with approximately equal affinity at both the CB₁ and CB₂ receptors, having a K_i of 8.0 nM at CB₁ and 7.0 nM at CB₂. It was originally discovered by, and named after,

John W. Huffman John William Huffman (1932–2022) was a professor of organic chemistry at Clemson University who first synthesised novel cannabinoids. His research, funded by the National Institute on Drug Abuse, was focused on making a drug to target endocanna ...

, but has subsequently been sold without his permission as an ingredient of synthetic cannabis smoking blends. Similar to the related 2'-

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

compound JWH-250, the 2'- bromo compound JWH-249, and the 2'-

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in ...

compound JWH-251, JWH-203 has a

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...

acetyl In organic chemistry, acetyl is a functional group with the chemical formula and the structure . It is sometimes represented by the symbol Ac (not to be confused with the element actinium). In IUPAC nomenclature, acetyl is called ethanoyl, ...

group in place of the naphthoyl ring used in most

amino In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent ...

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloa ...

indole Indole is an aromatic heterocyclic organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other c ...

cannabinoid compounds, and has the strongest ''in vitro'' binding affinity for the cannabinoid receptors of any compound in the phenylacetyl group. Unexpectedly despite its weaker CB₁ K_i ''in vitro'', the 2-methylindole derivative JWH-204 is actually more potent than JWH-203 in animal tests for cannabinoid activity, though it is still weaker than JWH-249.

Legal status

In the United States, JWH-203 is a Schedule I Controlled Substance. As of October 2015, JWH-203 is a controlled substance in China.

References

{{Use dmy dates, date=August 2019 JWH cannabinoids Phenylacetylindoles Chloroarenes Designer drugs CB1 receptor agonists CB2 receptor agonists

Legal status

See also

References