Forensic Toxicology

, Volume 30, Issue 2, pp 114–125 | Cite as

Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide (APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in illegal products

  • Nahoko Uchiyama
  • Maiko Kawamura
  • Ruri Kikura-Hanajiri
  • Yukihiro Goda
Original Article


Two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA, 1) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide (APINACA, 2), have been identified as designer drugs in illegal products being sold in Japan. The identification was based on liquid chromatography-mass spectrometry (LC-MS), gas chromatography-mass spectrometry (GC-MS), high-resolution MS and nuclear magnetic resonance (NMR) analyses. Both mass and NMR spectrometric data revealed that 1 was 1-pentyl-N-tricyclo[,7]dec-1-yl-1H-indole-3-carboxamide, and 2 was 1-pentyl-N-tricyclo[,7]dec-1-yl)-1H-indazole-3-carboxamide. Although many of the synthetic cannabinoids detected in illegal products, such as JWH-018, have a 3-carbonyl indole moiety, compounds 1 and 2 are a new type of synthetic cannabinoid having an amide and an adamantyl group, and 2 also has an indazole group in place of an indole group. There has been no synthetic, chemical, or biological information about 1 or 2 until now, making this the first report of these cannabimimetic compounds (1 and 2) as designer drugs. In addition, five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, are also described herein as newly distributed designer drugs in Japan.


N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide AM-1220 AM-2233 AM-1241 AM-1248 



This work was supported in part by a Health and Labor Sciences Research Grant from the Ministry of Health, Labour, and Welfare, Japan.


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Copyright information

© Japanese Association of Forensic Toxicology and Springer 2012

Authors and Affiliations

  • Nahoko Uchiyama
    • 1
  • Maiko Kawamura
    • 1
  • Ruri Kikura-Hanajiri
    • 1
  • Yukihiro Goda
    • 1
  1. 1.National Institute of Health SciencesTokyoJapan

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