Forensic Toxicology

, Volume 29, Issue 2, pp 95–110 | Cite as

Identification and quantitation of two benzoylindoles AM-694 and (4-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone, and three cannabimimetic naphthoylindoles JWH-210, JWH-122, and JWH-019 as adulterants in illegal products obtained via the Internet

  • Jun’ichi NakajimaEmail author
  • Misako Takahashi
  • Takako Seto
  • Chieko Kanai
  • Jin Suzuki
  • Masao Yoshida
  • Tomoko Hamano
Original Article


During our careful surveillance of unregulated drugs, we found five new compounds used as adulterants in herbal and drug-like products obtained via the Internet. These compounds were identified by liquid chromatography–mass spectrometry, gas chromatography–mass spectrometry, accurate mass spectrometry, and nuclear magnetic resonance spectroscopy. The first compound identified was a benzoylindole AM-694, which is 1-[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone (1). The second compound was (4-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone (2), which was also classified as a benzoylindole. The three other compounds were identified as naphthoylindoles JWH-210 (4-ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone; 3), JWH-122 (4-methylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone; 4), and JWH-019 (1-hexyl-3-(naphthalen-1-oyl)indole; 5). All compounds except compound 2 had been reported to be cannabinoid receptor agonists. For quantitation of the five compounds and previously reported compounds, each product was extracted with methanol under ultrasonication to prepare a test solution for analysis by liquid chromatography with ultraviolet detection. Each compound detected in 43 commercial products showed large variation in content ranging from 4.0 to 359 mg per pack.


AM-694 4-(Methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone JWH-210 JWH-122 JWH-019 Cannabimimetic indole 


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Copyright information

© Japanese Association of Forensic Toxicology and Springer 2011

Authors and Affiliations

  • Jun’ichi Nakajima
    • 1
    Email author
  • Misako Takahashi
    • 1
  • Takako Seto
    • 1
  • Chieko Kanai
    • 1
  • Jin Suzuki
    • 1
  • Masao Yoshida
    • 1
  • Tomoko Hamano
    • 1
  1. 1.Division of DrugsTokyo Metropolitan Institute of Public HealthTokyoJapan

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