Mass spectrometric properties of N-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new representative of designer drugs of NBOMe series and derivatives thereof / Shevyrin V., Kupriyanova O., Lebedev A.T., Melkozerov V., Eltsov O., Shafran Y., Morzherin Y., Sadykova R. // Journal of Mass Spectrometry. - 2016. - V. 51, l. 10. - P. 969-979.

ISSN:
10765174
Type:
Article
Abstract:
Emergence of new psychoactive substances, hallucinogenic phenethylamines in particular, in illicit market is a serious threat to human health in global scale. We have detected and identified N-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new compound in NBOMe series. Identification was achieved by means of gas chromatography/mass spectrometry (GC/MS), including high-resolution mass spectrometry with tandem experiments (GC/HRMS and GC/HRMS2), ultra-high performance liquid chromatography/high-resolution mass spectrometry with tandem experiments (UHPLC/HRMS and UHPLC/HRMS2), and 1H and 13C nuclear magnetic resonance spectroscopy. The peculiarities of fragmentation of the compound under electron ionization (EI) and collision-induced dissociation were studied. Despite of the empirical rule denying migration of the hydrogen atom in McLafferty rearrangement to the benzene ring with substituents in the both ortho-positions, it easily occurs for 2,4,6-TMPEA-NBOMe in EI conditions. We have noticed that electron-donating substituents, e.g. methoxy groups in the both ortho-positions and para-positions favor the rearrangement. For specially synthesized N-methyl and N-acyl derivatives McLafferty rearrangement is not observed. N-Acyl derivatives demonstrate McLafferty rearrangement, but the charge retains at the alternative fragment involving N-acyl carbonyl group. We have also showed that the hydrogen atoms in 2,4,6-trimethoxybenzene ring may be easily substituted for deuterium or for strong electrophiles like trifluoroacetyl. Analytical characteristics of 2,4,6-TMPEA-NBOMe and of some derivatives thereof which enable their determination in various criminal seizures are given. Copyright © 2016 John Wiley & Sons, Ltd. Copyright © 2016 John Wiley & Sons, Ltd.
Author keywords:
electrophilic substitution; high-resolution mass spectrometry; McLafferty rearrangement; NBOMe; psychoactive substances
Index keywords:
Atoms; Chromatography; Copyrights; Drug products; Gas chromatography; Health risks; High performance liquid chromatography; Ionization of gases; Liquid chromatography; Magnetic resonance spectroscopy;
DOI:
10.1002/jms.3808
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Affiliations Institute of Chemistry and Technology, Ural Federal University, 19 Mira St, Ekaterinburg, Russian Federation; Kazan Scientific Center, A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, 8 Arbuzov St, Kazan, Russian Federation; Organic Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow, Russian Federation; Main Agency of the Ministry of the Interior of the Russian Federation, Sverdlovsk Region Branch, Expert and Criminalistic Center, 17 Lenina Avenue, Ekaterinburg, Russian Federation; Kazan State Medical University, 49 Butlerov St, Kazan, Russian Federation
Author Keywords electrophilic substitution; high-resolution mass spectrometry; McLafferty rearrangement; NBOMe; psychoactive substances
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Correspondence Address Shevyrin, V.; Institute of Chemistry and Technology, Ural Federal University, 19 Mira St, Russian Federation; email: vadim.shevyrin@gmail.com
Publisher John Wiley and Sons Ltd
CODEN JMSPF
Language of Original Document English
Abbreviated Source Title J. Mass Spectrom.
Source Scopus