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

Abstract

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 C22H29N4O2F. 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)-1H-pyrazole-5-carboxamide. Compound 1, which is a new type of synthetic cannabinoid, has a 3-(4-fluorophenyl)-1H-pyrazole group in place of a 1H-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.”