Identification of a cannabimimetic indole as a designer drug in a herbal product
- 497 Downloads
A cannabimimetic indole has been identified as a new adulterant in a herbal product being sold illegally in Japan for its expected narcotic effect. Liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry analyses indicated that the product contained two major compounds. One was identified as a cannabinoid analog (1RS,3SR)-3-[4-(1,1-dimethyloctyl)-2-hydroxyphenyl]cyclohexan-1-ol (1) by direct comparison with the authentic compound, which we reported previously. The other compound (2) showed a molecular weight of 341 daltons, and accurate mass spectral measurements showed its elemental composition to be C24H23NO. Both mass and nuclear magnetic resonance spectrometric data revealed that 2 was 1-pentyl-3-(1-naphthoyl)indole [or naphthalen-1-yl-(1-pentylindol-3-yl)methanone] being identical to JWH-018, which was synthesized by Wiley and coworkers in 1998. This compound was reported as a potent cannabinoid receptor agonist possessing a pharmacological cannabimimetic activity.
Keywords1-Pentyl-3-(1-naphthoyl)indole Naphthalen-1-yl-(1-pentylindol-3-yl)methanone JWH-018 Cannabimimetic indole Designer drug Herbal product
Unable to display preview. Download preview PDF.
- 1.Uchiyama N, Kikura-Hanajiri R, Kawahara N, Haishima Y, Goda Y (2009) Identification of a cannabinoid analog as a new type of designer drug in a herbal product. Chem Pharm Bull 57(4), (in press)Google Scholar
- 6.Zweiundzwanzigste Verordnung, zur Änderung betäubungsmittelrechtlicher Vorschriften (2009), Germany. BGBl I Nr. 3 vom 21.01.2009, 22. BtMÄndV vom 19. Januar 2009, S. 49–50, http://www.bgblportal.de/BGBL/bgbl1f/bgbl109s0049.pdf. Accessed 19 Jan 2009
- 13.Rapaka RS, Makriyannis A (1987) Structure-activity relationships of the cannabinoids. NIDA Res Monogr 79: 1–216Google Scholar
- 23.D’Ambra TE, Estep KG, Bell MR, Eissenstat MA, Josef KA, Ward SJ, Haycock DA, Baizman ER, Casiano FM, Beglin NC, Chippari SM, Grego JD, Kullnig RK, Daley GT (1992) Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor. J Med Chem 35: 124–135PubMedCrossRefGoogle Scholar
- 27.Kulkarni SK, Ninan I (2001) Current concepts in cannabinoid pharmacology. Indian J Pharmacol 33: 170–184Google Scholar