JWH-015

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Chemical compound


JWH-015
INN
Drug class
Routes of administration
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status
CAS Number 155471-08-2
PubChem 4273754
DrugBank
ChemSpider 3480676
KEGG


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.[1] However, it still displays some CB1 activity, and in some model systems can be very potent and efficacious at activating CB1 receptors,[2] and therefore it is not as selective as newer drugs such as JWH-133.[3] It has been shown to possess immunomodulatory effects,[4][5] and CB2 agonists may be useful in the treatment of pain and inflammation.[6][7] It was discovered and named after John W. Huffman.

Metabolism[edit | edit source]

JWH-015 has been shown in vitro to be metabolized primarily by hydroxylation and N-dealkylation, and also by epoxidation of the naphthalene ring,[8] similar to the metabolic pathways seen for other aminoalkylindole cannabinoids such as WIN 55,212-2.[9] 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.[10]

Legal status[edit | edit source]

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-015 are Schedule I Controlled Substances.[11]

As of October 2015 JWH-015 is a controlled substance in China.[12]

JWH-015 has been classified under the German BtMG as Anlage II.[13]

References[edit | edit source]

  1. ↑ , Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2)receptor binding, Drug and Alcohol Dependence, Vol. 60(Issue: 2), pp. 133–140, DOI: 10.1016/S0376-8716(99)00152-0, PMID: 10940540,
  2. ↑ , The CB2-preferring agonist JWH015 also potently and efficaciously activates CB1 in autaptic hippocampal neurons, Pharmacological Research, Vol. 66(Issue: 5), pp. 437–442, DOI: 10.1016/j.phrs.2012.08.002, PMID: 22921769, PMC: 3601544,
  3. ↑ , Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor, Current Topics in Medicinal Chemistry, 2008, Vol. 8(Issue: 3), pp. 187–204, DOI: 10.2174/156802608783498014, PMID: 18289088,
  4. ↑ , Cannabinoid receptor CB2 modulates the CXCL12/CXCR4-mediated chemotaxis of T lymphocytes, Molecular Immunology, Vol. 43(Issue: 14), pp. 2169–2179, DOI: 10.1016/j.molimm.2006.01.005, PMID: 16503355,
  5. ↑ , CB2 cannabinoid receptor agonist JWH-015 modulates human monocyte migration through defined intracellular signaling pathways, American Journal of Physiology. Heart and Circulatory Physiology, Vol. 294(Issue: 3), pp. H1145–H1155, DOI: 10.1152/ajpheart.01328.2007, PMID: 18178718,
  6. ↑ , Prescribing and use of benzodiazepines: an epidemiologic perspective, Journal of Psychoactive Drugs, 1992, Vol. 24(Issue: 1), pp. 63–64, DOI: 10.1080/02791072.1992.10471620, PMID: 1352348,
  7. ↑ , Spinal cannabinoid receptor type 2 activation reduces hypersensitivity and spinal cord glial activation after paw incision, Anesthesiology, Vol. 106(Issue: 4), pp. 787–794, DOI: 10.1097/01.anes.0000264765.33673.6c, PMID: 17413917,
  8. ↑ , 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, Vol. 386(Issue: 5), pp. 1345–1355, DOI: 10.1007/s00216-006-0717-6, PMID: 16955257,
  9. ↑ , 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, Vol. 30(Issue: 10), pp. 1077–1086, DOI: 10.1124/dmd.30.10.1077, PMID: 12228183,
  10. ↑ , Inhibition of human tumour prostate PC-3 cell growth by cannabinoids R(+)-Methanandamide and JWH-015: involvement of CB2, British Journal of Cancer, Vol. 101(Issue: 6), pp. 940–950, DOI: 10.1038/sj.bjc.6605248, PMID: 19690545, PMC: 2743360,
  11. ↑ Template:UnitedStatesCode2
  12. ↑ 关于印发《非药用类麻醉药品和精神药品列管办法》的通知 Full text, , China Food and Drug Administration, 27 September 2015, Accessed on: 1 October 2015.
  13. ↑ Stoffe gem. Anlagen zum BtMG Full text, , Accessed on: 2024-11-23.


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Contributors: Prab R. Tumpati, MD