Structural analysis of an lysergic acid diethylamide (LSD) analogue N-methyl-N-isopropyllysergamide (MiPLA): Insights from Rotamers in NMR spectra

IF 2.6 3区医学 Q2 BIOCHEMICAL RESEARCH METHODS Drug Testing and Analysis Pub Date : 2023-10-13 DOI:10.1002/dta.3586

Takuji Shoda, Genichiro Tsuji, Maiko Kawamura, Takashi Kurohara, Takashi Misawa, Ruri Kikura-Hanajiri, Yosuke Demizu

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Abstract

Lysergic acid diethylamide (LSD) is a hallucinogenic compound that binds to and activates the serotonin 2A receptor and is classified as a controlled narcotic in Japan. Recently, MiPLA, an N-methyl-N-isopropyl derivative of LSD, has been detected in paper-sheet products in several countries. This study focuses on the synthesis of MiPLA and includes a comprehensive analysis involving structural and liquid chromatography–mass spectrometry (LC-MS). Particularly, MiPLA was synthesized in three-steps starting from ergometrine maleate, which resulted in the formation of (8S)-isomer, iso-MiPLA, as a by-product. The LC-MS results showed that LSD, MiPLA, and iso-MiPLA exhibited different retention times. Their chemical structures were determined using nuclear magnetic resonance spectroscopy, which revealed the presence of rotamers involving the N-methyl-N-isopropyl groups of tertiary amides in MiPLA and iso-MiPLA.

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麦角酸二乙酰胺（LSD）类似物N-甲基-N-异丙基麦角酰胺（MiPLA）的结构分析：NMR光谱中来自旋转异构体的见解。

赖氨酸二乙胺（LSD）是一种与血清素2A受体结合并激活的致幻化合物，在日本被列为受控麻醉剂。最近，在几个国家的纸张产品中检测到一种LSD的N-甲基-N-异丙基衍生物MiPLA。本研究的重点是MiPLA的合成，包括结构和液相色谱-质谱（LC-MS）的综合分析。特别地，以马来酸麦角新碱为原料，分三步合成了MiPLA，并作为副产物形成了（8S）-异构体异MiPLA。LC-MS结果表明，LSD、MiPLA和异MiPLA表现出不同的保留时间。使用核磁共振光谱测定了它们的化学结构，揭示了在MiPLA和异MiPLA中存在涉及叔酰胺的N-甲基-N-异丙基的旋转异构体。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Drug Testing and Analysis BIOCHEMICAL RESEARCH METHODS-CHEMISTRY, ANALYTICAL

CiteScore

5.90

自引率

24.10%

发文量

191

审稿时长

2.3 months

期刊介绍： As the incidence of drugs escalates in 21st century living, their detection and analysis have become increasingly important. Sport, the workplace, crime investigation, homeland security, the pharmaceutical industry and the environment are just some of the high profile arenas in which analytical testing has provided an important investigative tool for uncovering the presence of extraneous substances. In addition to the usual publishing fare of primary research articles, case reports and letters, Drug Testing and Analysis offers a unique combination of; ‘How to’ material such as ‘Tutorials’ and ‘Reviews’, Speculative pieces (‘Commentaries’ and ‘Perspectives'', providing a broader scientific and social context to the aspects of analytical testing), ‘Annual banned substance reviews’ (delivering a critical evaluation of the methods used in the characterization of established and newly outlawed compounds). Rather than focus on the application of a single technique, Drug Testing and Analysis employs a unique multidisciplinary approach to the field of controversial compound determination. Papers discussing chromatography, mass spectrometry, immunological approaches, 1D/2D gel electrophoresis, to name just a few select methods, are welcomed where their application is related to any of the six key topics listed below.