Etazene ( N,N -diethyl-2-{[(4-ethoxyphenyl)methyl]-1 H -benzimidazol-1-yl}-ethan-1-amine (dihydrochloride)): a novel ben
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ORIGINAL ARTICLE
Etazene (N,N‑diethyl‑2‑{[(4‑ethoxyphenyl) methyl]‑1H‑benzimidazol‑1‑yl}‑ethan‑1‑amine (dihydrochloride)): a novel benzimidazole opioid NPS identified in seized material: crystal structure and spectroscopic characterization Marta Siczek1 · Marcin Zawadzki1,2 · Miłosz Siczek3 · Agnieszka Chłopaś‑Konowałek2 · Paweł Szpot1,2 Received: 17 July 2020 / Accepted: 31 August 2020 © The Author(s) 2020
Abstract Purpose The aim of the study was to present the spectroscopic characteristics and crystal structure of the etazene—a benzimidazole opioid, which appeared on the illegal drug market in Poland in the last weeks. Methods The title compound was analyzed by X-ray crystallography as well as gas and liquid chromatography combined with mass spectrometry. Spectroscopic techniques have also been used, such as nuclear magnetic resonance, infrared and ultraviolet-visible spectroscopies. Results We presented the identification and the broad chemical characterization of etazene, a synthetic opioid that has recently been introduced on the illegal drug market. Conclusions In this paper, we described single-crystal X-ray, chromatographic and spectroscopic characterization of a synthetic opioid that emerged on the new psychoactive substance (NPS) market in Poland. To the best of our knowledge, this is the first full characterization of etazene. Analytical data presented in the work can be helpful in identification and detection of the NPS in forensic and clinical laboratories. Keywords Etazene · New psychoactive substance · Synthetic opioid · X-ray crystallography · NMR spectroscopy · Mass spectrometry
Introduction In recent years, an increase in the popularity of synthetic opioids on the illegal drug market has been observed, which is reflected in the annual reports of European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) [1–5]. Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11419-020-00552-9) contains supplementary material, which is available to authorized users. * Marcin Zawadzki [email protected] 1
Department of Forensic Medicine, Wroclaw Medical University, 4 J. Mikulicza‑Radeckiego Street, 50‑345 Wroclaw, Poland
2
Institute of Toxicology Research, 45 Kasztanowa Street, 55‑093 Borowa, Poland
3
Faculty of Chemistry, University of Wroclaw, 14 Joliot‑Curie, 50‑383 Wroclaw, Poland
Particularly many cases of intoxication have been reported in connection with the use of fentanyl derivatives, such as butyrfentanyl, 4-fluorobutyrfentanyl, furanylfentanyl, and 4-fluoroisobutyrfentanyl [6–11]. Recent months have, however, brought a new trend that can be attributed to the legislative changes introduced in China [12] in May 2019. The use of non-fentanyl synthetic opioids [13], including benzimidazole derivatives [14, 15], has started to appear on the European and American markets. The first papers on the synthesis and properties of benzimidazole opioids (Fig. 1) were published in 1957 and 1960 [16–23]. Already then it was signale
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