Gas Liquid Chromatographic and Mass Spectrometric Studies on Trimethylsilyl Derivatives of N-Methyl- and N,N-Dimethyltryptamines

N,N-dimethyltryptamines (DMT, 5-OMe-DMT, and bufotenin) were fully converted to trimethylsilyl derivatives with the TMS group attached to the indolic nitrogen. Gas-liquid chromatography data for these derivatives and mass spectrometry data from combined GC-MS analysis are reported. Secondary amines N-methyltryptamine and N-methylserotonin formed multiple derivatives, with the indolic NH reacting more readily than the secondary amino NH. Primary amines reacted with carbon disulfide to produce isothiocyanates that exhibit good gas chromatography properties and are well suited for GC-MS studies.

Study at a glance

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.