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Analytical characterization of N,N-diallyltryptamine (DALT) and 16 ring-substituted derivatives

Brandt, SD and Kavanagh, PV and Dowling, G and Talbot, B and Westphal, F and Meyer, MR and Maurer, HH and Halberstadt, AL (2016) Analytical characterization of N,N-diallyltryptamine (DALT) and 16 ring-substituted derivatives. Drug Testing and Analysis. ISSN 1942-7611

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Abstract

Many N,N-dialkylated tryptamines show psychoactive properties in humans and the number of derivatives involved in multidisciplinary areas of research has grown over the last few decades. Whereas some derivatives form the basis of a range of medicinal products, others are predominantly encountered as recreational drugs, and in some cases, the areas of therapeutic and recreational use can overlap. In recent years, 5-methoxy-N,N-diallyltryptamine (5-MeO-DALT) has appeared as a new psychoactive substance (NPS) and ‘research chemical’ whereas 4-acetoxy-DALT and the ring-unsubstituted DALT have only been detected very recently. Strategies pursued in the authors’ laboratories included the preparation and biological evaluation of previously unreported N,N-diallyltryptamines (DALTs). This report describes the analytical characterization of seventeen DALTs. Fifteen DALTs were prepared by a microwave-accelerated Speeter and Anthony procedure following established procedures developed previously in the authors’ laboratories. In addition to DALT, the substances included in this study were 2-phenyl-, 4-acetoxy-, 4-hydroxy-, 4,5-ethylenedioxy-, 5-methyl-, 5-methoxy-, 5-methoxy-2-methyl-, 5-ethoxy-, 5-fluoro-, 5-fluoro-2-methyl-, 5-chloro-, 5-bromo-, 5,6-methylenedioxy-, 6-fluoro-, 7-methyl, and 7-ethyl-DALT, respectively. The DALTs were characterized by nuclear magnetic resonance spectroscopy (NMR), gas chromatography (GC) quadrupole and ion trap (EI/CI) mass spectrometry (MS), low and high mass accuracy MS/MS, ultraviolet diode array detection and GC solid-state infrared analysis, respectively. A comprehensive collection of spectral data was obtained that are provided to research communities who face the challenge of encountering newly emerging substances where analytical data are not available. These data are also relevant to researchers who might wish to explore the clinical and non-clinical uses of these substances.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: Brandt, S. D., Kavanagh, P. V., Dowling, G., Talbot, B., Westphal, F., Meyer, M. R., Maurer, H. H., and Halberstadt, A. L. (2016) Analytical characterization of N,N-diallyltryptamine (DALT) and 16 ring-substituted derivatives. Drug Test. Analysis, doi: 10.1002/dta.1974., which has been published in final form at http://dx.doi.org/10.1002/dta.1974 This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving
Uncontrolled Keywords: 0301 Analytical Chemistry, 1115 Pharmacology And Pharmaceutical Sciences
Subjects: Q Science > QD Chemistry
R Medicine > RM Therapeutics. Pharmacology
R Medicine > RS Pharmacy and materia medica
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Wiley
Date Deposited: 15 Mar 2016 15:10
Last Modified: 26 Jul 2016 11:01
DOI or Identification number: 10.1002/dta.1974
URI: http://researchonline.ljmu.ac.uk/id/eprint/3241

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