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 January 1, 2005 Simon D. Brandt, Sally Freeman, Ian A. Fleet et al. 46 citations
The degree of alkylation of the side chain nitrogen in tryptamines influences psychoactivity. The Speeter and Anthony method, which reduces a substituted indole-3-yl-glyoxalylamide to the desired tryptamine with metal hydride, was used to synthesize 12 symmetrically and 13 asymmetrically N,N-disubstituted glyoxalylamides and their corresponding tryptamine derivatives. These compounds were characterized by gas chromatography EI-ion trap mass spectrometry, electrospray-triple quadrupole-tandem mass spectrometry, and NMR spectroscopy. A solvent dependency in NMR chemical shifts must be considered for unambiguous assignment. The 1H-NMR study allowed evaluation of rotamer populations of asymmetrical glyoxalylamides. For forensic or clinical monitoring, appropriate ion transitions focus on beta-cleavage and alpha-cleavage fragmentations. The analytical data aid in spectral identification of psychoactive tryptamines.