JWH-007

JWH-007
Legal status
Legal status
Identifiers
IUPAC name
  • 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)
SMILES
  • c14ccccc4cccc1C(=O)c3c2ccccc2n(c3C)CCCCC
InChI
  • 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]

Another drug similarly named JHW-007 (not JWH) is a cocaine analog (the di-para-fluoro benztropine, being essentially a hybrid between benzatropine and difluoropine; with fluorine groups in the former or being descarbmethoxy in the latter) and atypical dopamine reuptake inhibitor,[7] but is distinct from and not the same as this JWH-007.[8]

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-007 are Schedule I Controlled Substances.[9]

JWH-007 was banned in Sweden on 1 October 2010 as a hazardous good harmful to health, after being identified as an ingredient in "herbal" synthetic cannabis products.[10][11]

JWH-007 is illegal in Poland since 08.06.2010 on the basis of 'Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii' published in Dz.U. 2011 nr 105 poz. 614[12]

As of October 2015 JWH-007 is a controlled substance in China.[13]

See also

References

  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. Pharmacological characterization of three novel cannabinoid receptor agonists in the mouse isolated vas deferens. Eur J Pharmacol. 1995 Sep 25;284(3):241-7. 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): 1118–26. 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): 1395–411. 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): 133–40. doi:10.1016/S0376-8716(99)00152-0. PMID 10940540.
  7. ↑ Rothman RB, Baumann MH, Prisinzano TE, Newman AH (January 2008). "Dopamine transport inhibitors based on GBR12909 and benztropine as potential medications to treat cocaine addiction". Biochemical Pharmacology. 75 (1): 2–16. doi:10.1016/j.bcp.2007.08.007. PMC 2225585. PMID 17897630.
  8. ↑ Velázquez-Sánchez C, García-Verdugo JM, Murga J, Canales JJ (July 2013). "The atypical dopamine transport inhibitor, JHW 007, prevents amphetamine-induced sensitization and synaptic reorganization within the nucleus accumbens". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 44: 73–80. doi:10.1016/j.pnpbp.2013.01.016. PMID 23385166. S2CID 207410365.
  9. ↑ 21 U.S.C. § 812: Schedules of controlled substances
  10. ↑ Swedish Code of Statutes Regulation (2010:1086).
  11. ↑ "Swedish Code of Statutes Regulation (2010:1086). (pdf)" (PDF). Archived from the original (PDF) on 2011-07-28. Retrieved 2011-01-10.
  12. ↑ "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". ISAP. Retrieved 12 June 2011.
  13. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
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