2. Academic Validation
  3. 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

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

  • J Mass Spectrom. 2016 Oct;51(10):969-979. doi: 10.1002/jms.3808.
Vadim Shevyrin 1,  Olga Kupriyanova 2,  Albert T Lebedev 3,  Vladimir Melkozerov 4,  Oleg Eltsov 5,  Yuri Shafran 5,  Yuri Morzherin 5,  Raziya Sadykova 6
Affiliations

Affiliations

  • 1 Institute of Chemistry and Technology, Ural Federal University, 19 Mira St., Ekaterinburg, 620002, Russia. vadim.shevyrin@gmail.com.
  • 2 Kazan Scientific Center, A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, 8 Arbuzov St., Kazan, 420088, Russia.
  • 3 Organic Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow, 119991, Russia.
  • 4 Main Agency of the Ministry of the Interior of the Russian Federation, Sverdlovsk Region Branch, Expert and Criminalistic Center, 17 Lenina Avenue, Ekaterinburg, 620014, Russia.
  • 5 Institute of Chemistry and Technology, Ural Federal University, 19 Mira St., Ekaterinburg, 620002, Russia.
  • 6 Kazan State Medical University, 49 Butlerov St., Kazan, 420012, Russia.
PMID: 27388323 DOI: 10.1002/jms.3808
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 1 H and 13 C 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.

Keywords

McLafferty rearrangement; NBOMe; electrophilic substitution; high-resolution mass spectrometry; psychoactive substances.

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