JWH-015

Quality 0.50 · 1 view · Updated 2 months ago

Chemical compound

title: "JWH-015" 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-015" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 444488130 | IUPAC_name = (2-Methyl-1-propyl-1H-indol-3-yl)-1-naphthalenylmethanone | image = JWH-015.svg | image_class = skin-invert-image

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = Schedule II | legal_UK = Class B | legal_US = Schedule I | legal_DE = Anlage II | routes_of_administration =

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

| IUPHAR_ligand = 5558 | CAS_number_Ref = | CAS_number = 155471-08-2 | UNII_Ref = | UNII = W4FL204T10 | ATC_prefix = | ATC_suffix = | PubChem = 4273754 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 3480676

| C=23 | H=21 | N=1 | O=1 | smiles = CCCN1C(=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43)C | StdInChI_Ref = | StdInChI = 1S/C23H21NO/c1-3-15-24-16(2)22(20-12-6-7-14-21(20)24)23(25)19-13-8-10-17-9-4-5-11-18(17)19/h4-14H,3,15H2,1-2H3 | StdInChIKey_Ref = | StdInChIKey = LJSBBBWQTLXQEN-UHFFFAOYSA-N

JWH-015 is a chemical from the naphthoylindole family that acts as a subtype-selective cannabinoid agonist. Its affinity for CB2 receptors is 13.8 nM, while its affinity for CB1 is 383 nM, meaning that it binds almost 28 times more strongly to CB2 than to CB1. However, it still displays some CB1 activity, and in some model systems can be very potent and efficacious at activating CB1 receptors, and therefore it is not as selective as newer drugs such as JWH-133. It has been shown to possess immunomodulatory effects, and CB2 agonists may be useful in the treatment of pain and inflammation. It was discovered and named after John W. Huffman.

Metabolism

JWH-015 has been shown in vitro to be metabolized primarily by hydroxylation and N-dealkylation, and also by epoxidation of the naphthalene ring, similar to the metabolic pathways seen for other aminoalkylindole cannabinoids such as WIN 55,212-2. Epoxidation of polycyclic aromatic hydrocarbons (see for example benzo(a)pyrene toxicity) can produce carcinogenic metabolites, although there is no evidence to show that JWH-015 or other aminoalkylindole cannabinoids are actually carcinogenic in vivo. JWH-015 may signal certain cancers to shrink through a process called apoptosis.

Legal status

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-015 are Schedule I Controlled Substances.

As of October 2015 JWH-015 is a controlled substance in China.

JWH-015 has been classified under the German BtMG as Anlage II.

References

References

  1. (August 2000). "Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2)receptor binding". Drug and Alcohol Dependence.
  2. (November 2012). "The CB2-preferring agonist JWH015 also potently and efficaciously activates CB1 in autaptic hippocampal neurons". Pharmacological Research.
  3. (2008). "Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor". Current Topics in Medicinal Chemistry.
  4. (July 2006). "Cannabinoid receptor CB2 modulates the CXCL12/CXCR4-mediated chemotaxis of T lymphocytes". Molecular Immunology.
  5. (March 2008). "CB2 cannabinoid receptor agonist JWH-015 modulates human monocyte migration through defined intracellular signaling pathways". American Journal of Physiology. Heart and Circulatory Physiology.
  6. (1992). "Prescribing and use of benzodiazepines: an epidemiologic perspective". Journal of Psychoactive Drugs.
  7. (April 2007). "Spinal cannabinoid receptor type 2 activation reduces hypersensitivity and spinal cord glial activation after paw incision". Anesthesiology.
  8. (November 2006). "Identification of in vitro metabolites of JWH-015, an aminoalkylindole agonist for the peripheral cannabinoid receptor (CB2) by HPLC-MS/MS". Analytical and Bioanalytical Chemistry.
  9. (October 2002). "In vitro metabolism of R(+)-[2,3-dihydro-5-methyl-3-[(morpholinyl)methyl]pyrrolo [1,2,3-de]1,4-benzoxazinyl]-(1-naphthalenyl) methanone mesylate, a cannabinoid receptor agonist". Drug Metabolism and Disposition.
  10. (September 2009). "Inhibition of human tumour prostate PC-3 cell growth by cannabinoids R(+)-Methanandamide and JWH-015: involvement of CB2". British Journal of Cancer.
  11. {{UnitedStatesCode2. 21. 812. Schedules of controlled substances
  12. (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.
  13. "Stoffe gem. Anlagen zum BtMG".

::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. ::

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