JWH-203 (1-pentyl-3-(2-chlorophenylacetyl)indole) is an
analgesic chemical from the
phenylacetylindole family that acts as a
cannabinoidagonist with approximately equal affinity at both the
CB1 and
CB2 receptors, having a
Ki of 8.0 nM at CB1 and 7.0 nM at CB2. It was originally discovered by, and named after,
John W. Huffman, but has subsequently been sold without his permission as an ingredient of
synthetic cannabis smoking blends.[2] Similar to the related 2'-
methoxy compound
JWH-250, the 2'-
bromo compound
JWH-249, and the 2'-
methyl compound
JWH-251, JWH-203 has a
phenylacetyl group in place of the
naphthoyl ring used in most
aminoalkylindole cannabinoid compounds, and has the strongest in vitro binding affinity for the cannabinoid receptors of any compound in the phenylacetyl group.[3][4][5]
Unexpectedly despite its weaker CB1 Kiin 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.[6]
^Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, et al. (September 2005). "1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles". Bioorganic & Medicinal Chemistry Letters. 15 (18): 4110–3.
doi:
10.1016/j.bmcl.2005.06.008.
PMID16005223.
^Manera C, Tuccinardi T, Martinelli A (April 2008). "Indoles and related compounds as cannabinoid ligands". Mini Reviews in Medicinal Chemistry. 8 (4): 370–87.
doi:
10.2174/138955708783955935.
PMID18473928.
^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from
the original on 1 October 2015. Retrieved 1 October 2015.