Prediction of designer drugs: Synthesis and spectroscopic analysis of synthetic cathinone analogs that may appear on the Swedish drug market

Andreas Carlsson; Veronica Sandgren; Stefan Svensson; Peter Konradsson; Simon Dunne; Martin Josefsson; Johan Dahlén

doi:10.1002/dta.2366

Prediction of designer drugs: Synthesis and spectroscopic analysis of synthetic cathinone analogs that may appear on the Swedish drug market

Drug Test Anal. 2018 Feb 9. doi: 10.1002/dta.2366. Online ahead of print.

Authors

Andreas Carlsson^{1

2}, Veronica Sandgren², Stefan Svensson², Peter Konradsson², Simon Dunne¹, Martin Josefsson^{2

3}, Johan Dahlén²

Affiliations

¹ Swedish National Forensic Centre - NFC, Linköping, Sweden.
² Department of Physics, Chemistry and Biology, Linköping University, Sweden.
³ Department of Forensic Genetics and Forensic Toxicology, National Board of Forensic Medicine, Linköping, Sweden.

PMID: 29426062
DOI: 10.1002/dta.2366

Abstract

The use of hyphenated analytical techniques in forensic drug screening enables simultaneous identification of a wide range of different compounds. However, the appearance of drug seizures containing new substances, mainly new psychoactive substances (NPS), is steadily increasing. These new and other already known substances often possess structural similarities and consequently they exhibit spectral data with slight differences. This situation has made the criteria that ensure indubitable identification of compounds increasingly important. In this work, 6 new synthetic cathinones that have not yet appeared in any Swedish drug seizures were synthesized. Their chemical structures were similar to those of already known cathinone analogs of which 42 were also included in the study. Hence, a total of 48 synthetic cathinones making up sets of homologous and regioisomeric compounds were used to challenge the capabilities of various analytical techniques commonly applied in forensic drug screening, ie, gas chromatography-mass spectrometry (GC-MS), gas chromatography-Fourier transform infrared spectroscopy (GC-FTIR), nuclear magnetic resonance (NMR), and liquid chromatography quadrupole time-of-flight mass spectrometry (LC-QTOF-MS). Special attention was paid to the capabilities of GC-MS and GC-FTIR to distinguish between the synthetic cathinones and the results showed that neither GC-MS nor GC-FTIR alone can successfully differentiate between all synthetic cathinones. However, the 2 techniques proved to be complementary and their combined use is therefore beneficial. For example, the structural homologs were better differentiated by GC-MS, while GC-FTIR performed better for the regioisomers. Further, new spectroscopic data of the synthesized cathinone analogs is hereby presented for the forensic community. The synthetic work also showed that cathinone reference compounds can be produced in few reaction steps.

Keywords: gas-phase IR spectroscopy; mass spectrometry; nuclear magnetic resonance; synthesis; synthetic cathinones.