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Analytical characterization of bioactive N‐benzyl‐substituted phenethylamines and 5‐methoxytryptamines

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 (CF3, F, CH3, Cl, I, SCH3) 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.

Authors:   Simon D. Brandt, Simon P. Elliott, Pierce V. Kavanagh, Nicola M. Dempster, Markus R. Meyer, Hans H. Maurer, David E. Nichols
Journal:   Rapid Communications in Mass Spectrometry
Volume:   29
edition:   7
Year:   2015
Pages:   573
DOI:   10.1002/rcm.7134
Publication date:   02-Mar-2015
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