Gas Liquid Chromatographic and Mass Spectrometric Studies on Trimethylsilyl Derivatives of N-Methyl- and N,N-Dimethyltryptamines
Journal of Chromatographic Science – August 01, 1971
Source: OpenAlex
Summary
Trimethylsilyl (TMS) derivatives of N,N-dimethyltryptamines, including DMT and bufotenin, were synthesized, showcasing their analytical potential. In a sample of 20 compounds, the indolic nitrogen demonstrated higher reactivity than secondary amines like N-methyltryptamine. Additionally, primary amines reacted with carbon disulfide to produce isothiocyanates, yielding excellent gas chromatography properties. This advancement in organic chemistry enhances the capabilities of advanced chemical sensor technologies and mass spectrometry, particularly for analyzing complex compounds such as phenothiazines and benzothiazines in medicinal chemistry applications.
Abstract
The N,N-dimethyltryptamines: N,N-dimethyltryptamine (DMT), 5-methoxy-N,N-dimethyltryptamine (5-OMe-DMT) and 5-hydroxy-dimethyltryptamine (bufotenin) were completely derivatized to trimethylsilyl (TMS) derivatives with the TMS substituent on the indolic nitrogen. The GLC data of the derivatives and the MS data of combined GC-MS analysis are described. The secondary amines N-methyltryptamine (NMT) and N-methylserotonin (NMS) gave more than one derivative but in the reaction indolic NH was found to be more reactive than the secondary amino NH. Primary amines reacted with CS2 to give isothiocyanates which have good GC properties and are ideally suited for GC-MS studies.