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JWH-015
Systematic (IUPAC) name
(2-Methyl-1-propyl-1H-indol-3-yl)-1-naphthalenylmethanone
Identifiers
CAS number 155471-08-2
ATC code  ?
PubChem 4273754
Chemical data
Formula C23H21NO 
Mol. mass 327.43 g/mol
Therapeutic considerations
Pregnancy cat.  ?
Legal status Legal

JWH-015 is a chemical from the aminoalkylindole family, which 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]

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.

References

  1. ^ 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 Dependance 2000; 60:133-140.
  2. ^ Marriott KS, Huffman JW. Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor. Current Topics in Medicinal Chemistry. 2008;8(3):187-204. PMID 18289088
  3. ^ Ghosh S, Preet A, Groopman JE, Ganju RK. Cannabinoid receptor CB2 modulates the CXCL12/CXCR4-mediated chemotaxis of T lymphocytes. Molecular Immunology. 2006 Jul;43(14):2169-79. PMID 16503355
  4. ^ Montecucco F, Burger F, Mach F, Steffens S. CB2 cannabinoid receptor agonist JWH-015 modulates human monocyte migration through defined intracellular signaling pathways. American Journal of Physiology. Heart and Circulatory Physiology. 2008 Mar;294(3):H1145-55. PMID 18178718
  5. ^ Ehrhart J, Obregon D, Mori T, Hou H, Sun N, Bai Y, Klein T, Fernandez F, Tan J, Shytle RD. Stimulation of cannabinoid receptor 2 (CB2) suppresses microglial activation. Journal of Neuroinflammation. 2005 Dec 12;2:29. PMID 16343349
  6. ^ Romero-Sandoval A, Eisenach JC. Spinal cannabinoid receptor type 2 activation reduces hypersensitivity and spinal cord glial activation after paw incision. Anesthesiology. 2007 Apr;106(4):787-94. PMID 17413917
  7. ^ 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
  8. ^ Zhang Q, Ma P, Iszard M, Cole RB, Wang W, Wang G. 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. 2002 Oct;30(10):1077-86. PMID 12228183







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