Synthesis and analytical characterization of 1-(2-thienoyl)-6-allyl-nor-d-lysergic acid diethylamide (1T-AL-LAD).

IF 2.6 3区医学 Q2 BIOCHEMICAL RESEARCH METHODS

Drug Testing and Analysis Pub Date : 2024-06-23 DOI:10.1002/dta.3747

Yuki Okada, Hiroki Segawa, Tadashi Yamamuro, Kenji Kuwayama, Kenji Tsujikawa, Tatsuyuki Kanamori, Yuko T Iwata

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引用次数: 0

Abstract

Lysergic acid diethylamide (LSD) analogs have emerged as new psychoactive substances (NPS) since the mid-2010s, and new compounds continue to emerge for recreational use. Since the end of 2023, "1D-AL-LAD" appeared on X (formerly Twitter) and other websites. As for the compound "1D-LSD" (which also has "1D" in the name), several studies show that the ingredient of seized blotter paper printed "1D-LSD" was actually 1-(2-thienoyl)-LSD (1T-LSD). However, there are no reports of seizures of 1-(1,2-dimethylcyclobutanecarbonyl)-LSD (1D-LSD). Accordingly, it was considered that all or at least a certain percentage of "1D-AL-LAD (1-(1,2-dimethylcyclobutanecarbonyl)-6-allyl-nor-LSD)" is actually 1-(2-thienoyl)-6-allyl-nor-LSD (1T-AL-LAD). This compound is handled by a number of distributors as of April 2024; therefore, it should be characterized in advance if seized. In this study, 1T-AL-LAD was synthesized and characterized using nuclear magnetic resonance spectroscopy, Fourier transform-infrared spectroscopy, liquid chromatography/high-resolution mass spectrometry (LC/HRMS) and gas chromatography/MS (GC/MS). This compound was easily distinguished from previously reported lysergamides. There were some differences in the detectability of 1T-AL-LAD compared with other lysergamides using GC/MS and the fragmentation patterns in LC/HRMS. These differences can be reasonably explained. This information will be of help to determine this substance in seized materials should it emerge on the market.

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1-(2-thienoyl)-6-allyl-nor-d-lysergic acid diethylamide (1T-AL-LAD) 的合成和分析特性。

自 2010 年代中期以来，麦角酰二乙胺（LSD）类似物作为新精神活性物质（NPS）出现，用于娱乐的新化合物不断涌现。自 2023 年底以来，"1D-AL-LAD "出现在 X（前 Twitter）和其他网站上。至于化合物 "1D-LSD"（名称中也有 "1D"），一些研究表明，查获的印有 "1D-LSD "的吸墨纸的成分实际上是 1-（2-噻吩酰）-LSD（1T-LSD）。但是，没有关于缉获 1-（1,2-二甲基环丁烷羰基）-LSD（1D-LSD）的报告。因此，人们认为 "1D-AL-LAD（1-(1,2-二甲基环丁烷羰基)-6-烯丙基-去甲-LSD）"实际上是 1-(2-噻吩甲酰)-6-烯丙基-去甲-LSD（1T-AL-LAD）的全部或至少一定比例。截至 2024 年 4 月，许多分销商都在销售这种化合物；因此，如果查获这种化合物，应事先对其进行定性。本研究利用核磁共振光谱、傅立叶变换红外光谱、液相色谱/高分辨质谱法（LC/HRMS）和气相色谱/质谱法（GC/MS）合成了 1T-AL-LAD 并对其进行了鉴定。这种化合物很容易与之前报道的溶血酰胺区分开来。使用气相色谱/质谱法检测 1T-AL-LAD 与其他麦角酰菌胺的可检测性以及 LC/HRMS 中的碎片模式存在一些差异。这些差异可以得到合理的解释。如果市场上出现这种物质，这些信息将有助于确定缉获材料中是否含有这种物质。

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.