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 Vadim,Kupriyanova Olga,Lebedev Albert T.,Melkozerov Vladimir,Eltsov Oleg,Shafran Yuri,Morzherin Yuri,Sadykova Raziya // JOURNAL OF MASS SPECTROMETRY. - 2016. - V. 51, l. 10. - P. 969-979.

ISSN/EISSN:

1076-5174 / 1096-9888

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 H-1 and C-13 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 (c) 2016 John Wiley \& Sons, Ltd.

Author keywords:

NBOMe; McLafferty rearrangement; high-resolution mass spectrometry; psychoactive substances; electrophilic substitution GAS CHROMATOGRAPHY/MASS SPECTROMETRY; INTRAMOLECULAR HYDROGEN-TRANSFER; HIGH-RESOLUTION-MS; TOXICOLOGICAL DETECTION; GC-MS; 5-HT2A RECEPTORS; URINE; METABOLISM; PHENETHYLAMINES; IDENTIFICATION

DOI:

10.1002/jms.3808

Web of Science ID:

ISI:000385855400012

Соавторы в МНС:

Другие поля

Поле	Значение
Month	OCT
Publisher	WILEY-BLACKWELL
Address	111 RIVER ST, HOBOKEN 07030-5774, NJ USA
Language	English
EISSN	1096-9888
Keywords-Plus	GAS CHROMATOGRAPHY/MASS SPECTROMETRY; INTRAMOLECULAR HYDROGEN-TRANSFER; HIGH-RESOLUTION-MS; TOXICOLOGICAL DETECTION; GC-MS; 5-HT2A RECEPTORS; URINE; METABOLISM; PHENETHYLAMINES; IDENTIFICATION
Research-Areas	Biochemistry \& Molecular Biology; Chemistry; Spectroscopy
Web-of-Science-Categories	Biochemical Research Methods; Chemistry, Analytical; Spectroscopy
Author-Email	vadim.shevyrin@gmail.com
ResearcherID-Numbers	Shevyrin, Vadim/F-2416-2017
ORCID-Numbers	Shevyrin, Vadim/0000-0002-0369-0786
Number-of-Cited-References	51
Usage-Count-Last-180-days	9
Usage-Count-Since-2013	16
Journal-ISO	J. Mass Spectrom.
Doc-Delivery-Number	DZ4UI