Analysis of highly potent synthetic opioid nitazene analogs and their positional isomers

化学 质谱法 电喷雾电离 芬太尼 质谱 电子电离 类阿片 色谱法 阿片受体 电离 离子 受体 药理学 有机化学 生物化学 医学
作者
Tatsuyuki Kanamori,Yuki Okada,Hiroki Segawa,Tadashi Yamamuro,Kenji Kuwayama,Kenji Tsujikawa,Yuko Iwata
出处
期刊:Drug Testing and Analysis [Wiley]
卷期号:15 (4): 449-457 被引量:16
标识
DOI:10.1002/dta.3415
摘要

Four nitazenes (metonitazene, etonitazene, protonitazene, and isotonitazene), highly potent benzimidazole synthetic opioids, and their four nitro group positional isomers (isonitazenes) were synthesized and analyzed using infrared (IR) spectroscopy, gas chromatography/mass spectrometry (GC/MS), and liquid chromatography/mass spectrometry (LC/MS). In addition, the agonistic activity of all compounds at the human μ-opioid receptor was measured using a cell-based assay system. In the IR spectra, characteristic peaks for nitazenes and isonitazenes were observed. In GC/MS, all compounds were well separated on the chromatogram, although distinguishing nitazenes from the corresponding isonitazenes by electron ionization mass spectra was difficult. In LC/MS, all compounds were detected in both positive and negative modes of electrospray ionization. Characteristic fragment ions were observed in the product ion spectra of isonitazenes, enabling nitazenes to be distinguished from isonitazenes. All nitazenes tested demonstrated higher agonistic activity at the human μ-opioid receptors than the synthetic opioid fentanyl. The agonistic activities of isonitazenes were 11-35 times lower than those of the corresponding nitazenes. However, iso-etonitazene and iso-isotonitazene showed moderate activity similar to that of fentanyl, indicating that these drugs could cause poisoning at a comparable level as fentanyl, if these drugs are abused in the future.
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