title: Identification and analytical characterization of six synthetic cannabinoids NNL-3, 5F-NPB-22-7N, 5F-AKB-48-7N, 5F-EDMB-PINACA, EMB-FUBINACA, and EG-018.
abstract: Clinical and forensic toxicology laboratories are continuously confronted by analytical challenges when dealing with the new psychoactive substances phenomenon. The number of synthetic cannabinoids, the chemical diversity, and the speed of emergence make this group of compounds particularly challenging in terms of detection, monitoring, and responding. Three indazole 7N positional isomer synthetic cannabinoids, two ethyl 2-amino-3-methylbutanoate-type synthetic cannabinoids, and one 9H-carbazole substituted synthetic cannabinoid were identified in seized materials. These six synthetic cannabinoid derivatives included: 1H-benzo[d] [1,2,3]triazol-1-yl 1-(5-fluoropentyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (NNL-3, 1), quinolin-8-yl 1-(5-fluoropentyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (5F-NPB-22-7N, 2), N-((1 s,3 s)-adamantan-1-yl)-1-(5-fluoropentyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide (5F-AKB-48-7N, 3), ethyl 2-(1-(5-fluoropentyl)-1H-indazole-3-carboxamido)-3,3-dimethylbutanoate (5F-EDMB-PINACA, 4), ethyl 2-(1-(4-fluorobenzyl)-1H-indazole-3-carboxamido)-3-methylbutanoate (EMB-FUBINACA, 5), and naphthalen-1-yl(9-pentyl-9H-carbazol-3-yl)methanone (EG-018, 6). The identification was based on ultra-high-performance liquid chromatography-quadrupole time-of-flight-mass spectrometry (UHPLC-QTOF-MS), gas chromatography-mass spectrometry (GC-MS), and nuclear magnetic resonance spectroscopy (NMR). The analytical characterization of these six synthetic cannabinoids was described, so as to assist forensic laboratories in identifying these compounds or other substances with similar structure in their case work. To our knowledge, no analytical data about the compounds 1-5 have appeared until now, making this the first report on these compounds. The GC-MS data of 6 has been reported, but this study added the LC-MS, NMR, and Fourier transform infrared (FTIR), data to render the analytical data collection process more complete. Copyright © 2017 John Wiley & Sons, Ltd.
authors.affiliation: National Narcotics Laboratory, Drug Intelligence and Forensic Center of the Ministry of Public Security, 100193, No. 18 Dongbeiwang West Road, Haidian District, Beijing, China.
authors.forename: Cuimei
authors.identifier: http://orcid.org/0000-0001-9779-3489
authors.initials: C
authors.lastname: Liu
authors.affiliation: National Narcotics Laboratory, Drug Intelligence and Forensic Center of the Ministry of Public Security, 100193, No. 18 Dongbeiwang West Road, Haidian District, Beijing, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Jia
authors.affiliation: National Narcotics Laboratory, Drug Intelligence and Forensic Center of the Ministry of Public Security, 100193, No. 18 Dongbeiwang West Road, Haidian District, Beijing, China.
authors.forename: Zhendong
authors.initials: Z
authors.lastname: Hua
authors.affiliation: National Narcotics Laboratory, Drug Intelligence and Forensic Center of the Ministry of Public Security, 100193, No. 18 Dongbeiwang West Road, Haidian District, Beijing, China.
authors.forename: Zhenhua
authors.initials: Z
authors.lastname: Qian
mesh_terms: D002186:Cannabinoids / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D006801:Humans; D013287:Illicit Drugs / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods
chemical_list: D002186:Cannabinoids; D013287:Illicit Drugs
keywords: indazole 7N positional isomer; mass spectrometry; nuclear magnetic resonance; new psychoactive substances; structure identification; synthetic cannabinoids