Forensic Toxicology

, Volume 33, Issue 1, pp 84–92 | Cite as

Identification of N,N-bis(1-pentylindol-3-yl-carboxy)naphthylamine (BiPICANA) found in an herbal blend product in the Tokyo metropolitan area and its cannabimimetic effects evaluated by in vitro [35S]GTPγS binding assays

  • Jun’ichi Nakajima
  • Misako Takahashi
  • Nozomi Uemura
  • Takako Seto
  • Haruhiko Fukaya
  • Jin Suzuki
  • Masao Yoshida
  • Maiko Kusano
  • Hiroshi Nakayama
  • Kei Zaitsu
  • Akira Ishii
  • Takako Moriyasu
  • Dai Nakae
Original Article

Abstract

During our careful survey of unregulated psychotropic drugs in June 2013 in the Tokyo metropolitan area, we found a new compound in a herbal product. It was identified as an analog of NNEI (MN-24) and differed in that its molecule possessed another N-pentyl indole-carbonyl group: N, N-bis(1-pentylindol-3-yl-carboxy)naphtylamine (BiPICANA, compound 2). Compound 2 was purified by silica and octadecyl group bonded type silica gel (C18, ODS) columns and confirmed by liquid chromatography–mass spectrometry, accurate mass spectrometry, nuclear magnetic resonance spectroscopy, and X-ray crystallography. No pharmacological information on compound 2 has been reported previously; our experiments on the binding ability of compound 2 to cannabinoid receptors revealed that it has affinities for CB1 and CB2 receptors (EC50 = 3.80 and 8.77 × 10−7 M, respectively). This is the first report identifying compound 2 in a dubious herbal product and demonstrating its binding affinities to cannabinoid receptors. Binding affinities of azepane isomers (compounds 3 and 4) of AM-1220 and AM-2233, also found in commercial products in Japan, are also presented in this report.

Keywords

N,N-Bis(1-pentylindol-3-yl-carboxy)naphtylamine (BiPICANA) Azepane isomers of AM-1220 and AM-2233 [35S]GTPγS binding assay X-ray crystallographic analysis Synthetic cannabinoid 

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Copyright information

© Japanese Association of Forensic Toxicology and Springer Japan 2014

Authors and Affiliations

  • Jun’ichi Nakajima
    • 1
  • Misako Takahashi
    • 1
  • Nozomi Uemura
    • 1
  • Takako Seto
    • 1
  • Haruhiko Fukaya
    • 2
  • Jin Suzuki
    • 1
  • Masao Yoshida
    • 1
  • Maiko Kusano
    • 3
  • Hiroshi Nakayama
    • 3
  • Kei Zaitsu
    • 3
  • Akira Ishii
    • 3
  • Takako Moriyasu
    • 1
  • Dai Nakae
    • 1
  1. 1.Department of Pharmaceutical and Environmental SciencesTokyo Metropolitan Institute of Public HealthTokyoJapan
  2. 2.Instrumental Analysis CenterTokyo University of Pharmacy and Life ScienceHachiojiJapan
  3. 3.Department of Legal Medicine and BioethicsNagoya University Graduate School of MedicineNagoyaJapan

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