Microwave‐accelerated preparation and analytical characterization of 5‐ethoxy‐N,N‐dialkyl‐[α,α,β,β‐H4]‐ and [α,α,β,β‐D4]‐tryptamines
Ruchanok Tearavarich, Viwat Hahnvajanawong, Nicola M. Dempster, Paul F. Daley, Nicholas V. Cozzi, Simon D. Brandt
Drug Testing and Analysis December 29, 2010 DOI: 10.1002/dta.223 via OpenAlex
Summary
Twelve novel 5-ethoxy-N,N-dialkyl-tryptamines and their deuterated counterparts were synthesized using a microwave-accelerated reduction step that took 5 minutes in tetrahydrofuran at 150 °C. The resulting 24 tryptamines were characterized by nuclear magnetic resonance spectroscopy and gas chromatography ion trap mass spectrometry, revealing differential fragmentation of side-chain-related iminium ions. These compounds are intended as internal standards for bioanalytical and pharmacological assays, aiding identification of novel tryptamines from non-traditional sources, and are of immediate value in forensic, research, and public health contexts.
Study at a glance
| Characteristics | Synthesis and characterization Peer reviewed |
|---|---|
| Keywords | Tryptamines Iminium Tetrahydrofuran Mass spectrometry Alkoxy group |
| Citations | 10 |
| Key finding | Twelve novel 5-ethoxy-N,N-dialkyl-tryptamines and their deuterated counterparts were synthesized rapidly via microwave-accelerated reduction and characterized by spectroscopy and mass spectrometry. |
Abstract
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-H(4) ]-tryptamines and their [α,α,β,β-D(4) ]-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.