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Microwave‐accelerated preparation and analytical characterization of 5‐ethoxy‐ N , N ‐dialkyl‐[α,α,β,β‐H 4 ]‐ and [α,α,β,β‐D 4 ]‐tryptamines
Author(s) -
Tearavarich Ruchanok,
Hahnvajanawong Viwat,
Dempster Nicola,
Daley Paul F.,
Cozzi Nicholas V.,
Brandt Simon D.
Publication year - 2011
Publication title -
drug testing and analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.065
H-Index - 54
eISSN - 1942-7611
pISSN - 1942-7603
DOI - 10.1002/dta.223
Subject(s) - tryptamines , chemistry , iminium , tetrahydrofuran , mass spectrometry , alkoxy group , solvent , analytical chemistry (journal) , ion , alkyl , chromatography , organic chemistry , tryptamine , biochemistry
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. Copyright © 2010 John Wiley & Sons, Ltd.