JWH-019

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Chemical compound

title: "JWH-019" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["naphthoylindoles", "jwh-cannabinoids", "designer-drugs", "cb1-receptor-agonists", "cb2-receptor-agonists"] description: "Chemical compound" topic_path: "general/naphthoylindoles" source: "https://en.wikipedia.org/wiki/JWH-019" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| verifiedrevid = 451563324 | IUPAC_name = 1-Hexyl-3-(naphthalen-1-oyl)indole | image = JWH019.svg | image_class = skin-invert-image

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = Schedule II | legal_US = Schedule I | legal_DE = Anlage II | legal_UK = Class B | legal_status = Illegal in Sweden, I-N (Poland) | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 209414-08-4 | UNII_Ref = | UNII = 0Z73828O4J | ATC_prefix = | ATC_suffix = | PubChem = | DrugBank_Ref = | DrugBank = | ChemSpiderID = 24598813

| C=25 | H=25 | N=1 | O=1 | smiles = c3cccc2c3cccc2C(=O)c1cn(CCCCCC)c4c1cccc4 | StdInChI = 1S/C25H25NO/c1-2-3-4-9-17-26-18-23(21-14-7-8-16-24(21)26)25(27)22-15-10-12-19-11-5-6-13-20(19)22/h5-8,10-16,18H,2-4,9,17H2,1H3 | StdInChIKey = PALJPGHWDUHUPO-UHFFFAOYSA-N

JWH-019 is an analgesic chemical from the naphthoylindole family that acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is the N-hexyl homolog of the more common synthetic cannabinoid compound JWH-018. Unlike the butyl homolog JWH-073, which is several times weaker than JWH-018, the hexyl homolog is only slightly less potent, although extending the chain one carbon longer to the heptyl homolog JWH-020 results in dramatic loss of activity. These results show that the optimum side chain length for CB1 binding in the naphthoylindole series is the five-carbon pentyl chain, shorter than in the classical cannabinoids where a seven-carbon heptyl chain produces the most potent compounds. This difference is thought to reflect a slightly different binding conformation adopted by the naphthoylindole compounds as compared to the classical cannabinoids, and may be useful in characterizing the active site of the CB1 and CB2 receptors.

Legal status

China

As of October 2015 JWH-019 is a controlled substance in China.

Poland

In Poland, JWH-019 is I-N (Poland).

Sweden

JWH-019 is illegal in Sweden.

United Kingdom

JWH-019 is Class B in the United Kingdom.

United States

JWH-019 is a Schedule I controlled substance, controlled federally in the United States.

Germany

JWH-019 has been classified under the BtMG as Anlage II.

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. (August 2000). "Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding". Drug and Alcohol Dependence.
  3. (January 2008). "Targeting the cannabinoid CB2 receptor: modelling and structural determinants of CB2 selective ligands". British Journal of Pharmacology.
  4. (2008). "Cannabinoid CB1 and CB2 receptor ligand specificity and the development of CB2-selective agonists". Current Medicinal Chemistry.
  5. (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.
  6. [https://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf Controlled Substances listed by the DEA]
  7. "Stoffe gem. Anlagen zum BtMG".

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naphthoylindolesjwh-cannabinoidsdesigner-drugscb1-receptor-agonistscb2-receptor-agonists