JWH-015
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| Systematic (IUPAC) name | |
| (2-Methyl-1-propyl-1H-indol-3-yl)-1-naphthalenylmethanone | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Legal |
| Identifiers | |
| CAS number | 155471-08-2  |
| ATC code | ? |
| PubChem | CID 4273754 |
| Chemical data | |
| Formula | C23H21NO |
| Mol. mass | 327.43 g/mol |
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JWH-015 is a chemical from the naphthoylindole family that acts as a subtype-selective cannabinoid agonist. Its affinity for CB2 receptors is 13.8nM, while its affinity for CB1 is 383nM, meaning that it binds almost 28x more strongly to CB2 than CB1.[1] However it still displays some weak CB1 activity, and is not as selective as newer drugs such as JWH-133.[2] It has been shown to possess immunomodulatory effects,[3][4] and CB2 agonists may be useful in the treatment of pain and inflammation.[5][6] It was discovered and named after Dr. John W. Huffman.
[edit] Metabolism
JWH-015 has been shown in vitro to be metabolised primarily by hydroxylation and N-dealkylation, and also by epoxidation of the naphthalene ring,[7] similar to the metabolic pathways seen for other aminoalkylindole cannabinoids such as WIN 55,212-2.[8] Epoxidation of polycyclic aromatic hydrocarbons can produce carcinogenic metabolites, although there is no evidence to show that JWH-015 or other aminoalkylindole cannabinoids are actually carcinogenic in vivo.
[edit] References
- ^ Aung MM, Griffin G, Huffman JW, Wu MJ, Keel C, Yang B, Showalter VM, Abood ME, Martin BR. Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence 2000; 60:133-140.
- ^ Marriott KS, Huffman JW (2008). "Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor". Current Topics in Medicinal Chemistry 8 (3): 187–204. doi:10.2174/156802608783498014. PMID 18289088.
- ^ Ghosh S, Preet A, Groopman JE, Ganju RK (2006). "Cannabinoid receptor CB2 modulates the CXCL12/CXCR4-mediated chemotaxis of T lymphocytes". Molecular immunology 43 (14): 2169–79. doi:10.1016/j.molimm.2006.01.005. PMID 16503355.
- ^ Montecucco F, Burger F, Mach F, Steffens S (2008). "CB2 cannabinoid receptor agonist JWH-015 modulates human monocyte migration through defined intracellular signaling pathways". American journal of physiology. Heart and circulatory physiology 294 (3): H1145–55. doi:10.1152/ajpheart.01328.2007. PMID 18178718.
- ^ Ehrhart J, Obregon D, Mori T, Hou H, Sun N, Bai Y, Klein T, Fernandez F et al. (2005). "Stimulation of cannabinoid receptor 2 (CB2) suppresses microglial activation". Journal of neuroinflammation 2: 29. doi:10.1186/1742-2094-2-29. PMC 1352348. PMID 16343349. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1352348.
- ^ Romero-Sandoval A, Eisenach JC (2007). "Spinal cannabinoid receptor type 2 activation reduces hypersensitivity and spinal cord glial activation after paw incision". Anesthesiology 106 (4): 787–94. doi:10.1097/01.anes.0000264765.33673.6c. PMID 17413917.
- ^ Zhang Q, Ma P, Cole RB, Wang G. 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. 2006 Nov;386(5):1345-55. PMID 16955257
- ^ Zhang Q, Ma P, Iszard M, Cole RB, Wang W, Wang G (2002). "In vitro metabolism of R(+)-2,3-dihydro-5-methyl-3-(morpholinyl)methylpyrrolo 1,2,3-de1,4-benzoxazinyl-(1-naphthalenyl) methanone mesylate, a cannabinoid receptor agonist". Drug metabolism and disposition: the biological fate of chemicals 30 (10): 1077–86. doi:10.1124/dmd.30.10.1077. PMID 12228183.
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