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
Publication type: Journal Article
Publication date: 2012-04-11
scimago Q2
wos Q2
SJR: 0.589
CiteScore: 6.0
Impact factor: 3.0
ISSN: 18608965, 18608973
Pathology and Forensic Medicine
Toxicology
Biochemistry (medical)
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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Total citations:
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UCHIYAMA N. 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 // Forensic Toxicology. 2012. Vol. 30. No. 2. pp. 114-125.
GOST all authors (up to 50)
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UCHIYAMA N., KAWAMURA M., KIKURA-HANAJIRI R., Goda Y. 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 // Forensic Toxicology. 2012. Vol. 30. No. 2. pp. 114-125.
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RIS
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TY - JOUR
DO - 10.1007/s11419-012-0136-7
UR - https://doi.org/10.1007/s11419-012-0136-7
TI - 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
T2 - Forensic Toxicology
AU - UCHIYAMA, Nahoko
AU - KAWAMURA, Maiko
AU - KIKURA-HANAJIRI, Ruri
AU - Goda, Yukihiro
PY - 2012
DA - 2012/04/11
PB - Springer Nature
SP - 114-125
IS - 2
VL - 30
SN - 1860-8965
SN - 1860-8973
ER -
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@article{2012_UCHIYAMA,
author = {Nahoko UCHIYAMA and Maiko KAWAMURA and Ruri KIKURA-HANAJIRI and Yukihiro Goda},
title = {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},
journal = {Forensic Toxicology},
year = {2012},
volume = {30},
publisher = {Springer Nature},
month = {apr},
url = {https://doi.org/10.1007/s11419-012-0136-7},
number = {2},
pages = {114--125},
doi = {10.1007/s11419-012-0136-7}
}
Cite this
MLA
Copy
UCHIYAMA, Nahoko, 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.” Forensic Toxicology, vol. 30, no. 2, Apr. 2012, pp. 114-125. https://doi.org/10.1007/s11419-012-0136-7.