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JWH-007

Not to be confused with JHW-007, an atypical dopamine reuptake inhibitor.
JWH-007
Legal status
Legal status
Identifiers
  • 1-Pentyl-2-methyl-3-(1-naphthoyl)indole
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H25NO
Molar mass355.481 g·mol−1
3D model (JSmol)
  • c14ccccc4cccc1C(=O)c3c2ccccc2n(c3C)CCCCC
  • InChI=1S/C25H25NO/c1-3-4-9-17-26-18(2)24(22-14-7-8-16-23(22)26)25(27)21-15-10-12-19-11-5-6-13-20(19)21/h5-8,10-16H,3-4,9,17H2,1-2H3
  • Key:IBBNKINXTRKICJ-UHFFFAOYSA-N
  (verify)

JWH-007 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It was first reported in 1994 by a group including the noted cannabinoid chemist John W. Huffman.[1][2] It was the most active of the first group of N-alkyl naphoylindoles discovered by the team led by John W Huffman, several years after the family was initially described with the discovery of the N-morpholinylethyl compounds pravadoline (WIN 48,098), JWH-200 (WIN 55,225) and WIN 55,212-2 by the Sterling Winthrop group.[3] Several other N-alkyl substituents were found to be active by Huffman's team including the n-butyl, n-hexyl, 2-heptyl, and cyclohexylethyl groups, but it was subsequently determined that the 2-methyl group on the indole ring is not required for CB1 binding, and tends to increase affinity for CB2 instead.[4][5] Consequently, the 2-desmethyl derivative of JWH-007, JWH-018, has slightly higher binding affinity for CB1, with an optimum binding of 9.00 nM at CB1 and 2.94 nM at CB2, and JWH-007 displayed optimum binding of 9.50 nM at CB1 and 2.94 nM at CB2.[6]

  1. ^ Huffman JW, Dai D, Martin BR, Compton DR (1994). "Design, Synthesis and Pharmacology of Cannabimimetic Indoles". Bioorganic & Medicinal Chemistry Letters. 4 (4): 563–566. doi:10.1016/s0960-894x(01)80155-4.
  2. ^ Pertwee RG, Griffin G, Lainton JA, Huffman JW (September 1995). "Pharmacological characterization of three novel cannabinoid receptor agonists in the mouse isolated vas deferens". European Journal of Pharmacology. 284 (3): 241–247. doi:10.1016/0014-2999(95)00318-f. PMID 8666005.
  3. ^ Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR (December 1992). "Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol". The Journal of Pharmacology and Experimental Therapeutics. 263 (3): 1118–1126. PMID 1335057.
  4. ^ Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, et al. (January 2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists". Bioorganic & Medicinal Chemistry. 13 (1): 89–112. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
  5. ^ Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry. 12 (12): 1395–1411. doi:10.2174/0929867054020864. PMID 15974991.
  6. ^ 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 CB(1) and CB(2) receptor binding". Drug and Alcohol Dependence. 60 (2): 133–140. doi:10.1016/S0376-8716(99)00152-0. PMID 10940540.

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