Comprehensive analytical characteristics of N -(adamantan-1-yl)-1- (cyclohexylmethyl)-1 H -indazole-3-carboxamide (ACHMI
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SHORT COMMUNICATION
Comprehensive analytical characteristics of N‑(adamantan‑1‑yl)‑1‑ (cyclohexylmethyl)‑1H‑indazole‑3‑carboxamide (ACHMINACA) Michal P. Dybowski1 · Piotr Holowinski1 · Rafal Typek1 · Andrzej L. Dawidowicz1 Received: 10 July 2020 / Accepted: 10 August 2020 © The Author(s) 2020
Abstract Purpose The aim of this study was to clarify the most essential analytical features of N-(adamantan-1-yl)1-(cyclohexylmethyl)-1H-indazole-3-carboxamide (one of the newest cannabimimetics called ACHMINACA), to make them useful for analytical identification of this compound. Methods The compound was analyzed by gas chromatography–mass spectrometry, high-resolution liquid chromatography–mass spectrometry, crystal X-ray diffraction and spectroscopic methods such as nuclear magnetic resonance, Raman, and infrared spectroscopies. Results Detailed and comprehensive analytical data have been acquired for ACHMINACA. Conclusions Although brief descriptions of the partial data of ACHMINACA have appeared recently, this article provides the most detailed and comprehensive analytical data of ACHMINACA to our knowledge. Our data will significantly broaden the knowledge about the compound structure extending the possibility of its orthogonal analysis. The gathered data are useful for forensic, toxicological, and clinical purposes. Keywords ACHMINACA · Analytical characteristics · Mass spectrometry · X-ray crystallography · Infrared, Raman and UV-VIS spectroscopies · NMR spectroscopy
Introduction A characteristic feature of the contemporary market of illegal substances is the huge supply of novel psychoactive compounds. Hundreds of them have been registered over the last 10 years by specialized European and United Nations offices, such as the European Monitoring Centre for Drugs and Drug Addiction and the United Nations Office on Drugs and Crime [1, 2]. Among them, synthetic cannabinoids constitute one of the most numerous and widespread groups. Their structural evolvement started with the modification of compounds containing the cyclohexylphenol or arylindole ketone core [3, 4]. Over the course of 10 years, many Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11419-020-00547-6) contains supplementary material, which is available to authorized users. * Michal P. Dybowski [email protected] 1
Department of Chromatography, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie Sklodowska University in Lublin, 20‑031 Lublin, Poland
derivatives of these compounds have appeared on the market, e.g., indole- and indazole carboesters, indole- and indazole carboxamides, indole-2,2,3,3-tetramethylcyclopropyl ketones, pyrazole carboxamides and other groups [5–9]. A multitude of substituents meeting the requirements for the cannabimimetic activity that can be attached to the enlisted core scaffolds and possible regioisomerism [4, 10–12] further expand the structural variety of synthetic cannabinoids. Until recent years, synthetic cannabinoids with adamantyl (tricyclo
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