Microwave-accelerated preparation and analytical characterization of 5-ethoxy-N,N-dialkyl-[α,α,β,β-H4]- and [α,α,β,β-D4]-tryptamines

The increased interest in N,N‐dialkyl tryptamines is a reflection of their diverse range of biologically active properties. Deuterated derivatives are of interest for use as internal standards in bioanalytical or pharmacological assays. The present study reports on the synthesis of twelve novel 5‐ethoxy‐N,N‐dialkyl‐[α,α,β,β‐H4]‐tryptamines and their [α,α,β,β‐D4]‐counterparts following the Speeter and Anthony procedure. The normally time‐consuming reduction step was carried out in 5 min under microwave‐accelerated conditions. Good yields were obtained using tetrahydrofuran as the solvent at 150 °C. The resulting 24 tryptamines have been characterized by 1D/2D nuclear magnetic resonance spectroscopy and gas chromatography ion trap mass spectrometry. Differential fragmentation of side‐chain‐related iminium ions has been observed as a key principle. Because many N,N‐dialkyltryptamines are available outside of traditional pharmaceutical supply chains as so‐called ‘research chemicals’, the availability, as standards, of these new N,N‐dialkyltryptamines will aid in identifiying novel tryptamines arising from these other souces. They should therefore be of immediate value within forensic, research, and public health contexts. Copyright © 2010 John Wiley & Sons, Ltd. Many tryptamine derivatives show psychoactive properties in humans. A rapid microwave‐accelerated preparation of twelve 5‐ethoxy‐N,N‐dialkyl‐[α,α,β,β‐H4]‐tryptamines and twelve 5‐ethoxy‐N,N‐dialkyl‐[α,α,β,β‐D4]‐tryptamines is described. Analytical characterization of these novel compounds was carried out by 1D/2D NMR, GC‐EI‐MS and GC‐CI‐MS/MS.