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Structural elucidation and identification of a new derivative of phenethylamine using quadrupole time‐of‐flight mass spectrometry
Author(s) -
Sekuła Karolina,
Zuba Dariusz
Publication year - 2013
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.6667
Subject(s) - chemistry , mass spectrometry , designer drug , phenethylamine , electron ionization , chromatography , electrospray ionization , tandem mass spectrometry , mass spectrum , context (archaeology) , analytical chemistry (journal) , ion , stereochemistry , organic chemistry , ionization , drug , psychology , paleontology , biology , psychiatry
RATIONALE In recent years, the phenomenon of uncontrolled distribution of new psychoactive substances that were marketed without prior toxicological studies has been observed. Because many designer drugs are related in chemical structure, the potential for misidentifying them is an important problem. It is therefore essential to develop an analytical procedure for unequivocal elucidation of the structures of these compounds. The issue has been discussed in the context of 25I‐NBMD [2‐(4‐iodo‐2,5‐dimethoxyphenyl)‐ N ‐[(2,3‐methylenedioxyphenyl)methyl]ethanamine], a psychoactive substance first discovered on the drug market in 2012. METHODS The substance was extracted from blotter papers with methanol. Separation was achieved via liquid chromatography. Analysis was conducted by electrospray ionization quadrupole time‐of‐flight mass spectrometry (ESI‐QTOFMS). Identification of the psychoactive component was supported by electron impact gas chromatography/mass spectrometry (GC/EI‐MS). RESULTS The high accuracy of the LC/ESI‐QTOFMS method allowed the molecular mass of the investigated substance (M exp = 441.0438 Da; mass error, ∆m = 0.2 ppm) and the formulae of ions formed during fragmentation to be determined. The main ions were recorded at m/z = 135.0440, 290.9876 and 305.9981. Structures of the obtained ions were elucidated in the tandem mass spectrometry (MS/MS) experiments by comparing them to mass spectra of previously detected derivatives of phenethylamine. CONCLUSIONS The performed study indicated the potential for using LC/QTOFMS method to identify new designer drugs. This technique can be used supplementary to standard GC/MS. Prior knowledge of the fragmentation mechanisms of phenethylamines allowed to predict the mass spectra of the novel substance – 25I‐NBMD. Copyright © 2013 John Wiley & Sons, Ltd.