Identification of two lysergic acid diethylamide analogs, 1-(3-(trimethylsilyl) propionyl) lysergic acid diethylamide (1S-LSD) and 1-(2-thienoyl)-6-allyl-nor-d-lysergic acid diethylamide (1T-AL-LAD), in paper sheet products distributed on the internet.

IF 2.8 4区医学 Q2 TOXICOLOGY

Forensic Toxicology Pub Date : 2025-04-03 DOI:10.1007/s11419-025-00718-3

Rie Tanaka, Maiko Kawamura, Michiho Ito, Ruri Kikura-Hanajiri

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引用次数: 0

Abstract

Purpose: Recently, numerous lysergic acid diethylamide (LSD) analogs have emerged as designer drugs globally. These compounds are mainly distributed as sheet products. In this study, two new LSD analogs were identified from sheet products.

Methods: The structures of the compounds were determined by gas chromatography-mass spectrometry, liquid chromatography-photodiode array-mass spectrometry, liquid chromatography with hybrid quadrupole time-of-flight mass spectrometry and nuclear magnetic resonance (NMR) measurement.

Results: From the NMR analysis, two compounds in the products were identified as N,N-diethyl-7-methyl-4-(3-(trimethylsilyl)propanoyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (1S-LSD) and 7-allyl-N,N-diethyl-4-(thiophene-2-carbonyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (1T-AL-LAD). In the product where 1S-LSD was detected, the presence of a trace amount of iso-1S-LSD, a C8-epimerization product of 1S-LSD, was suggested.

Conclusions: This paper is the first to report the detection of 1S-LSD and 1T-AL-LAD in sheet products in Japan. Notably, the metabolic pathways and biological activities of 1S-LSD and 1T-AL-LAD are not explored. The possibility of the in vivo deacylation and conversion of the compoundsinto LSD or AL-LAD should be further investigated.

查看原文本刊更多论文

两种麦角酸二乙基酰胺类似物，1-（3-（三甲基硅基）丙酰）麦角酸二乙基酰胺（1S-LSD）和1-（2-硫烯基）-6-烯丙基-未-d-麦角酸二乙基酰胺（1T-AL-LAD）在网上分销的纸张产品中的鉴定。

目的：近年来，全球范围内出现了许多麦角酸二乙胺（LSD）类似物作为设计药物。这些化合物主要以片状产品的形式分布。本研究从片状产品中鉴定出两种新的LSD类似物。方法：采用气相色谱-质谱法、液相色谱-光电二极管阵列-质谱法、液相色谱-混合四极杆飞行时间质谱法和核磁共振法测定化合物的结构。结果：经核磁共振鉴定，产物中有2个化合物分别为N，N-二乙基-7-甲基-4-（3-（三甲基硅基）丙基）-4,6,6a,7,8,9-六氢吲哚[4,3-fg]喹啉-9-羧酰胺（s - lsd）和7-烯丙基-N，N-二乙基-4-（噻吩-2-羰基）-4,6,6a,7,8,9-六氢吲哚[4,3-fg]喹啉-9-羧酰胺（1T-AL-LAD）。在检测到1S-LSD的产品中，存在微量的iso-1S-LSD，这是1S-LSD的c8外聚产物。结论：本文首次报道了日本薄板产品中检测出1S-LSD和1T-AL-LAD。值得注意的是，没有对1S-LSD和1T-AL-LAD的代谢途径和生物活性进行探讨。这些化合物体内脱酰和转化为LSD或AL-LAD的可能性有待进一步研究。

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

Forensic Toxicology TOXICOLOGY-

CiteScore

5.80

自引率

9.10%

发文量

审稿时长

3 months

期刊介绍： The journal Forensic Toxicology provides an international forum for publication of studies on toxic substances, drugs of abuse, doping agents, chemical warfare agents, and their metabolisms and analyses, which are related to laws and ethics. It includes original articles, reviews, mini-reviews, short communications, and case reports. Although a major focus of the journal is on the development or improvement of analytical methods for the above-mentioned chemicals in human matrices, appropriate studies with animal experiments are also published. Forensic Toxicology is the official publication of the Japanese Association of Forensic Toxicology (JAFT) and is the continuation of the Japanese Journal of Forensic Toxicology (ISSN 0915-9606).