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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

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Abstract

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[3.3.1.13,7]dec-1-yl-1H-indole-3-carboxamide, and 2 was 1-pentyl-N-tricyclo[3.3.3.1.3,7]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.

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Acknowledgments

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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Authors and Affiliations

  1. National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo, 158-8501, Japan

    Nahoko Uchiyama, Maiko Kawamura, Ruri Kikura-Hanajiri & Yukihiro Goda

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  1. Nahoko Uchiyama
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  2. Maiko Kawamura
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  3. Ruri Kikura-Hanajiri
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  4. Yukihiro Goda
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Correspondence to Yukihiro Goda.

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Uchiyama, N., Kawamura, M., Kikura-Hanajiri, R. et al. 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. Forensic Toxicol 30, 114–125 (2012). https://doi.org/10.1007/s11419-012-0136-7

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