JWH-015

JWH-015
Legal status
Legal status
Identifiers
  • (2-Methyl-1-propyl-1H-indol-3-yl)-1-naphthalenylmethanone
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.161.912 Edit this at Wikidata
Chemical and physical data
FormulaC23H21NO
Molar mass327.427 g·mol−1
3D model (JSmol)
  • CCCN1C(=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43)C
  • InChI=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 ☒N
  • Key:LJSBBBWQTLXQEN-UHFFFAOYSA-N ☒N
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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 13.8 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.

  1. ^ Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, et al. (August 2000). "Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2)receptor binding". Drug and Alcohol Dependence. 60 (2): 133–140. doi:10.1016/S0376-8716(99)00152-0. PMID 10940540.
  2. ^ Murataeva N, Mackie K, Straiker A (November 2012). "The CB2-preferring agonist JWH015 also potently and efficaciously activates CB1 in autaptic hippocampal neurons". Pharmacological Research. 66 (5): 437–442. doi:10.1016/j.phrs.2012.08.002. PMC 3601544. PMID 22921769.
  3. ^ 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.
  4. ^ Ghosh S, Preet A, Groopman JE, Ganju RK (July 2006). "Cannabinoid receptor CB2 modulates the CXCL12/CXCR4-mediated chemotaxis of T lymphocytes". Molecular Immunology. 43 (14): 2169–2179. doi:10.1016/j.molimm.2006.01.005. PMID 16503355.
  5. ^ Montecucco F, Burger F, Mach F, Steffens S (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. 294 (3): H1145–H1155. doi:10.1152/ajpheart.01328.2007. PMID 18178718. S2CID 5896815.
  6. ^ Balter MB, Uhlenhuth EH (1992). "Prescribing and use of benzodiazepines: an epidemiologic perspective". Journal of Psychoactive Drugs. 24 (1): 63–64. doi:10.1080/02791072.1992.10471620. PMID 1352348.
  7. ^ Romero-Sandoval A, Eisenach JC (April 2007). "Spinal cannabinoid receptor type 2 activation reduces hypersensitivity and spinal cord glial activation after paw incision". Anesthesiology. 106 (4): 787–794. doi:10.1097/01.anes.0000264765.33673.6c. PMID 17413917.