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

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.

Analytical characterization of “etonitazepyne,” a new pyrrolidinyl‐containing 2‐benzylbenzimidazole opioid sold online

“…The obtained 1 H‐NMR spectrum is shown in Figure 5. Similar to the described 1 H NMR spectrum of isotonitazene and etazene 19 protons of both phenyl and benzimidazole rings gave signals in a range characteristic for aromatic systems (6.9–8.3 ppm): aromatic protons of ethoxyphenyl unit gave two doublets at 7.33 and 6.89 ppm, whereas signals from the benzimidazole ring could be observed at 8.49, 8.19, and 7.96 ppm (see Figure 5). Singlet derived from methylene bridge between phenyl and benzimidazole ring appeared in the spectrum at 4.39 ppm.…”

Etazene induces developmental toxicity in vivo Danio rerio and in silico studies of new synthetic opioid derivative

“…ETZ (2-[2-[(4-ethoxyphenyl)methyl]benzimidazol-1-yl]- N , N -diethylethanamine; PubChem CID: 149,797,386) was provided for research purposes by the Institute of Toxicology Research (Borowa, Poland) as a part of actions by the Polish police. Identification and purity check was done by X-ray crystallography, 1 H and 13 C spectroscopies, LC–MS/MS and GC–MS chromatography, UV–VIS and FT-IR spectroscopy techniques and already has been published in previous work 34 . Acetonitrile, methanol, H 2 O formic acid, all LC–MS grades were purchased from Sigma-Aldrich (Germany).…”

“…Sample was diluted with methanol and 10 μL was transferred to a 150 μL vial with a cap containing 80 μL of methanol and 10 μL of internal standard (IS) (4-MMC- d 3 , 1 μg/mL). Solution was transferred to silanized glass insert and analyzed by UPLC-QQQ-MS with already developed method 34 .…”

Exploring the Versatility of Benzimidazole Scaffolds as Medicinal Agents: A Brief Update

“…The antimicrobial activity was screened and was found that (89) showed maximum potency against all gram-positive and gram-negative bacteria. Also, (88) actively functions as an antifungal agent. These derivatives also interact with active sites of E. coli and can be accounted for inhibition of E. coli topoisomerase I (Figure 22).…”

“…The prominence of benzimidazole in the field of medicine is exceptional. Etazene (106), a benzimidazole opioid that has got strong activity, is used as a new psychoactive substance (Figure 27) [88]. Misuse of certain benzimidazole derivatives can create social crises too.…”