Analytical profile of N-ethyl-N-cyclopropyl lysergamide (ECPLA), an isomer of lysergic acid 2,4-dimethylazetidide (LSZ).,Drug Testing and Analysis

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Analytical profile of N-ethyl-N-cyclopropyl lysergamide (ECPLA), an isomer of lysergic acid 2,4-dimethylazetidide (LSZ).
Drug Testing and Analysis ( IF 2.6 ) Pub Date : 2020-08-16 , DOI: 10.1002/dta.2911
Simon D Brandt ₁ , Pierce V Kavanagh ₂ , Folker Westphal ₃ , Alexander Stratford ₄ , Simon P Elliott ₅ , Geraldine Dowling _{2,

6} , Adam L Halberstadt _{7,

8}

Affiliation

Recent investigations have shown that N‐ethyl‐N‐cyclopropyl lysergamide (ECPLA) produces LSD‐like behavioral effects in mice, which suggests that it may act as a hallucinogen in humans. Although the use of ECPLA as a recreational drug has been limited, key analytical data that can be used to detect ECPLA are required for future forensic and clinical investigations. ECPLA is an isomer of (2′S,4′S)‐lysergic acid 2,4‐dimethylazetidide (LSZ), a lysergamide that emerged as a recreational drug in 2013. Several analytical approaches were examined, including single‐ and tandem mass spectrometry platforms at low and high resolution, gas‐ and liquid chromatography (GC, LC), nuclear magnetic resonance spectroscopy (NMR), and GC condensed‐phase infrared spectroscopy (GC‐sIR). ECPLA and LSZ could be differentiated by NMR, GC‐sIR, GC, and LC‐based methods. The electron ionization mass spectra of ECPLA and LSZ contained ion clusters typically observed with related lysergamides such as m/z 150–155, m/z 177–182, m/z 191–197, m/z 205–208, and m/z 219–224. One of the significant differences in abundance related to these clusters included ions at m/z 196 and m/z 207/208. The base peaks were detected at m/z 221 in both cases followed by the retro‐Diels‐Alder fragment at m/z 292. Minor but noticeable differences between the two isomers could also be seen in the relative abundance of m/z 98 and m/z 41. Electrospray ionization mass spectra included lysergamide‐related ions at m/z 281, 251, 223, 208, 197, 180, and 140. LSZ (but not ECPLA) showed product ions at m/z 267 and m/z 98 under the conditions used.

中文翻译：

N-乙基-N-环丙基麦角酰胺 (ECPLA) 的分析图，一种麦角酸 2,4-二甲基氮杂环丁烷 (LSZ) 的异构体。

最近的研究表明，N-乙基-N-环丙基麦角酰胺 (ECPLA) 在小鼠中产生类似 LSD 的行为效应，这表明它可能在人类中充当致幻剂。尽管 ECPLA 作为消遣性药物的使用受到限制，但未来的法医和临床调查仍需要可用于检测 ECPLA 的关键分析数据。ECPLA 是 (2' S ,4' S的异构体)-麦角酸 2,4-二甲基氮杂环丁烷 (LSZ)，一种于 2013 年作为娱乐药物出现的麦角酰胺。研究了几种分析方法，包括低分辨率和高分辨率的单质谱和串联质谱平台、气相色谱和液相色谱 ( GC、LC)、核磁共振光谱 (NMR) 和 GC 凝聚相红外光谱 (GC-sIR)。ECPLA 和 LSZ 可以通过 NMR、GC-sIR、GC 和基于 LC 的方法进行区分。ECPLA 和 LSZ 的电子电离质谱包含离子簇，通常用相关的麦角酰胺观察到，例如 m/z 150–155、m/z 177–182、m/z 191–197、m/z 205–208 和 m/ z 219–224。与这些簇相关的丰度显着差异之一包括 m/z 196 和 m/z 207/208 处的离子。

更新日期：2020-10-04

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