Structure via PubChem · Public domain (PubChem)
JWH-203
Sign in to saveJWH-203 (1-pentyl-3-(2-chlorophenylacetyl)indole) is an analgesic chemical from the phenylacetylindole family that acts as a cannabinoid agonist 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. 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 the Vinony graph
Within Vinony's link graph, JWH-203 is referenced by 453 other articles, and connects out to synthetic cannabinoid, JWH-210 and synhexyl.
It is catalogued under topics including 2-Chlorophenyl compounds, CB1 receptor agonists and CB2 receptor agonists.
Its subject is documented across 6 Wikipedia language editions.
Chemical data
- Formula
- C21H22ClNO
- Molecular weight
- 339.9 g/mol
- IUPAC name
- 2-(2-chlorophenyl)-1-(1-pentylindol-3-yl)ethanone
- SMILES
- CCCCCN1C=C(C2=CC=CC=C21)C(=O)CC3=CC=CC=C3Cl
- InChIKey
- YDINKDBAZJOSLV-UHFFFAOYSA-N
- XLogP
- 5.6
- Polar surface area
- 22 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 339.139
Show 2 more facts
- chemical formula
- C₂₁H₂₂ClNO
- canonical SMILES
- CCCCCN1C=C(C2=CC=CC=C21)C(=O)CC3=CC=CC=C3Cl
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Legal status
- See also
- References
JWH-203 (1-pentyl-3-(2-chlorophenylacetyl)indole) is an analgesic chemical from the phenylacetylindole family that acts as a cannabinoid agonist 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. 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.
Unexpectedly despite its weaker CB1 Ki 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.
Excerpted from Wikipedia’s “JWH-203” article, available under the CC BY-SA 4.0 licence.