A new pyrazole-carboxamide type synthetic cannabinoid AB-CHFUPYCA [N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxamide] identified in illegal products

A new pyrazole-carboxamide type synthetic cannabinoid, AB-CHFUPYCA ( 1 ), was detected in illegal herbal products by our ongoing survey in Japan. The structure of 1 was identified by gas chromatography–mass spectrometry (GC–MS), liquid chromatography–mass spectrometry (LC–MS), liquid chromatography–...

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Bibliographic Details
Published in:Forensic toxicology 2015-07, Vol.33 (2), p.367-373
Main Authors: Uchiyama, Nahoko, Asakawa, Kazuhiro, Kikura-Hanajiri, Ruri, Tsutsumi, Taizo, Hakamatsuka, Takashi
Format: Article
Language:English
Subjects:
Forensic Medicine
Forensic Science
Medical Law
Medicinal Chemistry
Medicine
Medicine & Public Health
Original Article
Pharmacology/Toxicology
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Summary:A new pyrazole-carboxamide type synthetic cannabinoid, AB-CHFUPYCA ( 1 ), was detected in illegal herbal products by our ongoing survey in Japan. The structure of 1 was identified by gas chromatography–mass spectrometry (GC–MS), liquid chromatography–mass spectrometry (LC–MS), liquid chromatography–high-resolution-mass spectrometry (LC–HR-MS) and nuclear magnetic resonance (NMR) analyses. Compound 1 showed a molecular weight of 400, and accurate mass measurement using LC–HR-MS revealed its molecular formula to be C 22 H 29 N 4 O 2 F. The MS and NMR spectrometric data revealed that the structure of 1 was N -(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-3-(4-fluorophenyl)-1 H -pyrazole-5-carboxamide. Compound 1 , which is a new type of synthetic cannabinoid, has a 3-(4-fluorophenyl)-1 H -pyrazole group in place of a 1 H -indazole group of AB-CHMINACA. To our knowledge, data on the chemistry and pharmacology of compound 1 have never been reported, and we therefore named compound 1 “AB-CHFUPYCA.”
ISSN:1860-8965
1860-8973
DOI:10.1007/s11419-015-0283-8