JWH-203

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Chemical compound

title: "JWH-203" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["jwh-cannabinoids", "phenylacetylindoles", "2-chlorophenyl-compounds", "designer-drugs", "cb1-receptor-agonists", "cb2-receptor-agonists"] description: "Chemical compound" topic_path: "general/jwh-cannabinoids" source: "https://en.wikipedia.org/wiki/JWH-203" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| verifiedrevid = 451554581 | IUPAC_name = 2-(2-Chlorophenyl)-1-(1-pentylindol-3-yl)ethanone | image = JWH-203.svg | image_class = skin-invert-image | width = 150

| tradename = | pregnancy_AU = | pregnancy_US = | legal_AU = | legal_CA = Schedule II | legal_UK = Class B | legal_US = Schedule I | legal_DE = Anlage II | legal_status = I-N (Poland)

| CAS_number_Ref = | CAS_number = 864445-54-5 | CAS_supplemental = (JWH-203)864445-55-6 (JWH-204) | UNII_Ref = | UNII = 52CP80V8FY | PubChem = 44397500 | ChemSpiderID = 23256082

| C=21 | H=22 | Cl=1 | N=1 | O=1 | smiles = Clc2ccccc2CC(=O)c1cn(CCCCC)c3ccccc13 | StdInChI = 1S/C21H22ClNO/c1-2-3-8-13-23-15-18(17-10-5-7-12-20(17)23)21(24)14-16-9-4-6-11-19(16)22/h4-7,9-12,15H,2-3,8,13-14H2,1H3 | StdInChIKey = YDINKDBAZJOSLV-UHFFFAOYSA-N

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.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/4/4b/JWH-204.svg" caption="JWH-204]]{{clear left}}"] ::

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

References

  1. "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych.
  2. (July 2011). "Analytical data for identification of the Cannabimimetic Phenylacetylindole JWH-203". Journal of Analytical Toxicology.
  3. (September 2005). "1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles". Bioorganic & Medicinal Chemistry Letters.
  4. (April 2008). "Indoles and related compounds as cannabinoid ligands". Mini Reviews in Medicinal Chemistry.
  5. (July 2011). "Analytical data for identification of the Cannabimimetic Phenylacetylindole JWH-203". Journal of Analytical Toxicology.
  6. (June 2012). "1-Pentyl-3-phenylacetylindoles and JWH-018 share in vivo cannabinoid profiles in mice". Drug and Alcohol Dependence.
  7. "Controlled Substances". [[Drug Enforcement Administration]].
  8. (27 September 2015). "关于印发《非药用类麻醉药品和精神药品列管办法》的通知". China Food and Drug Administration.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

jwh-cannabinoidsphenylacetylindoles2-chlorophenyl-compoundsdesigner-drugscb1-receptor-agonistscb2-receptor-agonists