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Analysis of Fragmentation Pathways of New-Type Synthetic Cannabinoids Using Electrospray Ionization
Journal of the American Society for Mass Spectrometry ( IF 3.1 ) Pub Date : 2018-06-27 , DOI: 10.1007/s13361-018-2008-9
Karolina Sekuła 1 , Dariusz Zuba 1 , Karolina Lorek 1
Affiliation  

Recently, dozens of new psychoactive substances have appeared on the European drug market every year. The most abundant group of these compounds is synthetic cannabinoids. In the first few years of the “legal highs” phenomenon, JWH (John W. Huffman) compounds were especially popular among drug users. However, the group of synthetic cannabinoids is constantly expanding, as new compounds are created by replacing known structural elements with different chemical groups. The problem with the identification of novel substances in forensic laboratories results from the structural similarity of the compounds and the rapid introduction of newer designer drugs on the black market. In this study, the fragmentation patterns of 29 new-type synthetic cannabinoids using electrospray ionization were investigated. The analysis was performed using quadrupole time-of-flight mass spectrometry. Based on measurements carried out under various conditions, the way of fragmentation of the tested compounds that were divided into groups due to their chemical structure was established. The study showed that the bond between the carbon atom of the carbonyl group and the ring or NH group attached to the ring was mainly cleaved. This mechanism was adequate for the fragmentation of first-generation synthetic cannabinoids. This paper presents characteristic ions formed by synthetic cannabinoids (i.e., ions originating from an indole/indazole ring and an adamanyl/naphthalene/quinoline ring) using electrospray ionization. Knowledge of these specific fragments can be used in forensic laboratories to determine the structure of novel compounds from the group of synthetic cannabinoids.

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中文翻译:

电喷雾电离分析新型合成大麻素的裂解途径

最近,每年在欧洲毒品市场上都会出现数十种新型精神活性物质。这些化合物中含量最高的是合成大麻素。在“合法高潮”现象出现的头几年,JWH(约翰·霍夫曼(John W. Huffman))化合物在吸毒者中特别受欢迎。然而,随着通过用不同化学基团取代已知的结构元素产生新的化合物,合成大麻素的种类正在不断扩大。法医实验室中鉴定新物质的问题是由于这些化合物的结构相似性以及在黑市上迅速引入新型设计药物所致。在这项研究中,研究了29种新型电喷雾电离合成大麻素的碎裂模式。使用四极杆飞行时间质谱仪进行分析。基于在各种条件下进行的测量,建立了由于其化学结构而分为几类的被测化合物的断裂方式。研究表明,羰基的碳原子与连接在环上的环或NH基团之间的键主要被裂解。这种机制足以使第一代合成大麻素片段化。本文介绍了使用电喷雾电离合成大麻素形成的特征离子(即源自吲哚/吲唑环和金刚烷基/萘/喹啉环的离子)。

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更新日期:2018-06-27
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