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

Brandt, SD and Elliott, SP and Kavanagh, PV and Dempster, NM and Meyer, MR and Maurer, HH and Nichols, DE (2015) Analytical characterization of bioactive N-benzyl-substituted phenethylamines and 5-methoxytryptamines. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 29 (7). pp. 573-584. ISSN 0951-4198

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Abstract

RationaleSubstances 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.ResultsThe 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.

Item Type: Article
Additional Information: This is the accepted version of the following article: "Analytical characterization of bioactive N-benzyl-substituted phenethylamines and 5-methoxytryptamines", which has been published in final form at http://dx.doi.org/10.1002/rcm.7134
Uncontrolled Keywords: 03 Chemical Sciences, 04 Earth Sciences, 06 Biological Sciences
Subjects: R Medicine > RM Therapeutics. Pharmacology
R Medicine > RS Pharmacy and materia medica
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Wiley
Related URLs:
Date Deposited: 11 Apr 2016 14:09
Last Modified: 11 Apr 2016 14:09
DOI or Identification number: 10.1002/rcm.7134
URI: http://researchonline.ljmu.ac.uk/id/eprint/3409

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