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
2016
Shevyrin, Vadim | Kupriyanova, Olga | Lebedev, Albert T. | Melkozerov, Vladimir | Eltsov, Oleg | Shafran, Yuri | Morzherin, Yuri | Sadykova, Raziya
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.
Show more [+] Less [-]AGROVOC Keywords
Bibliographic information
This bibliographic record has been provided by National Agricultural Library