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Analytical characterization of bioactive N ‐benzyl‐substituted phenethylamines and 5‐methoxytryptamines
Author(s) -
Brandt Simon D.,
Elliott Simon P.,
Kavanagh Pierce V.,
Dempster Nicola M.,
Meyer Markus R.,
Maurer Hans H.,
Nichols David E.
Publication year - 2015
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.7134
Subject(s) - chemistry , phenethylamines , characterization (materials science) , organic chemistry , combinatorial chemistry , stereochemistry , nanotechnology , materials science
Rationale Substances based on the N ‐(2‐methoxybenzyl)phenethylamine template ('NBOMe' derivatives) play an important role in medicinal research but some of these derivatives have also appeared as 'research chemicals' for recreational use which has attracted attention worldwide. A major challenge associated with newly emerging substances includes the lack of analytical data and the ability to correctly identify positional isomers. Methods Six N ‐benzylphenethylamines based on the 2,5‐dimethoxy‐4‐iodophenethylamine structure ('25I') and twelve substituted N ‐benzyl‐5‐methoxytryptamines ('5MT') have been prepared and extensively characterized. Techniques used for characterization were gas chromatography/ion trap mass spectrometry in electron and chemical ionization mode, liquid chromatography/diode array detection (DAD), infrared spectroscopy, electrospray high mass accuracy quadrupole time‐of‐flight tandem mass spectrometry, and triple quadrupole tandem mass spectrometry. Results The characterization of 18 'NBOMe' compounds provided a comprehensive collection of chromatographic and spectral data. Four groups of three positional isomers, i.e. 25I‐NB2OMe, 25I‐NB3OMe, 25I‐NB4OMe, 25I‐NB2B, 25I‐NB3B, 25I‐NB4B and their 5‐methoxytryptamine counterparts, were included and assessed for ability to obtain differentiation. Six meta ‐substituted N ‐benzyl derivatives of 5‐methoxytryptamine (CF 3 , F, CH 3 , Cl, I, SCH 3 ) were also studied. Conclusions The implementation of mass spectral techniques was helpful for the differentiation between isomers, for example, when considering the difference in a number of ion ratios. This was considered beneficial in cases where chromatographic separation was only partially achieved under liquid chromatography (LC) conditions. The use of LC/DAD analysis was also found to be valuable for this particular purpose, which confirmed the integrative value of complementary techniques used in areas related to forensic toxicology. Copyright © 2015 John Wiley & Sons, Ltd.