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Issue 9, 2005
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Analytical chemistry of synthetic routes to psychoactive tryptamines
Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS

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Abstract

Twelve symmetrically and 13 asymmetrically N,N-disubstituted glyoxalylamide precursors and their corresponding tryptamine derivatives have been characterised by gas chromatography low-pressure chemical ionisation ion trap tandem mass spectrometry (CI-IT-MS-MS) with internal (in situ) ionisation using methanol as the chemical ionisation reagent. Mass spectral differences and similarities between the investigated compounds are discussed and put into context with previous investigations. In tryptamines the formation of [CH2[double bond, length as m-dash]N+R2R3] iminium ions after β-cleavage appears to be the dominating process. Dissociation of the protonated molecule into [3-vinylindole]+ for example, appears to be a minor pathway when compared with electrospray triple quadrupole tandem mass spectrometry (ESI-TQ-MS-MS) where this ion transition was found to be of distinctive importance. CI-IT-MS-MS is also found to enable the differentiation between most isomeric derivatives studied.

Graphical abstract: Analytical chemistry of synthetic routes to psychoactive tryptamines Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS

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Publication details

The article was received on 18 Mar 2005, accepted on 13 Jun 2005 and first published on 08 Jul 2005


Article type: Paper
DOI: 10.1039/B504001A
Citation: Analyst, 2005,130, 1258-1262
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    Analytical chemistry of synthetic routes to psychoactive tryptamines

    S. D. Brandt, S. Freeman, I. A. Fleet and J. F. Alder, Analyst, 2005, 130, 1258
    DOI: 10.1039/B504001A

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