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
Study at a glance
AI-extracted from the abstract| Characteristics | Analytical chemistry study Peer reviewed |
|---|---|
| Population | N,N-disubstituted glyoxalylamide precursors and their tryptamine derivatives |
| Keywords | Tryptamines Iminium Tandem mass spectrometry Chemical ionization Protonation Electrospray ionization Reagent Selected reaction monitoring Analytical chemistry journal Chromatography Organic chemistry |
| Citations | 10 |
| Key points | In tryptamines, formation of [CH2=N+R2R3] iminium ions after beta-cleavage dominates, while dissociation into [3-vinylindole]+ is a minor pathway compared to electrospray triple quadrupole tandem mass spectrometry. |
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=N+R2R3] iminium ions after beta-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.
Citations in the library
Cited by 5
- Analysis of Designer Drugs Detected in the Products Purchased in Fiscal Year 2006 Yakugaku Zasshi October 1, 2008
- Characterization of the synthesis of N,N‐dimethyltryptamine by reductive amination using gas chromatography ion trap mass spectrometry Drug Testing and Analysis July 1, 2010
- Microwave‐accelerated preparation and analytical characterization of 5‐ethoxy‐N,N‐dialkyl‐[α,α,β,β‐H4]‐ and [α,α,β,β‐D4]‐tryptamines Drug Testing and Analysis December 29, 2010
- Halogenated solvent interactions with N,N-dimethyltryptamine: formation of quaternary ammonium salts and their artificially induced rearrangements during analysis. Forensic Science International July 4, 2008
- DMT analogues: N-ethyl-N-propyltryptamine and N-allyl-N-methytryptamine as their hydrofumarate salts Acta Crystallographica. Section E, Crystallographic Communications July 3, 2020
Cites 2
- Analytical chemistry of synthetic routes to psychoactive tryptamines : Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR The Analyst 2005
- Analytical chemistry of synthetic routes to psychoactive tryptamines : Part I. Characterisation of the Speeter and Anthony synthetic route to 5-methoxy-N,N-diisopropyltryptamine using ESI-MS-MS and ESI-TOF-MS The Analyst 2004