Identification of (2-aminopropyl)indole positional isomers in forensic samples.

Identification of (2-aminopropyl)indole positional isomers in forensic samples.
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法医样品中(2-氨基丙基)吲哚位置异构体的鉴定。

DOI:
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发表时间:
2014
影响因子:
2.9
通讯作者:
P. Kavanagh
P. Kavanagh
中科院分区:
医学3区
文献类型:
--
作者:
K. Scott;J. Power;S. McDermott;J. O’Brien;Brian Talbot;Michael G Barry;P. Kavanagh

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2012年,挪威当局通过预警系统向欧洲毒品和毒瘾监测中心报告了5-(2-氨基丙基)吲哚(5-API,5-IT)。3-异构体3-(2-氨基丙基)吲哚(3-API,AMT,α-甲基色胺)在娱乐性药物市场上销售的时间较长,芬兰当局于2001年首次向欧洲毒品和毒瘾监测中心报告。这两种异构体都可以从“法律的高度”的在线供应商处获得。最近,三个法医药物案例(两个片剂和一个粉末)被提交用于常规分析,活性成分被初步鉴定为API异构体。合成了6种位置异构体(2-、3-、4-、5-、6-和7-(2-氨丙基)吲哚),并通过气相色谱-质谱(GC-MS)和液相色谱-质谱(LC-MS)组合进行分析,结果表明这些异构体易于区分,从而有助于鉴别片剂中的3-API和粉末中的5-API。除了共洗脱的5-和6-API外,发现可以通过GC分离异构体而无需衍生化。液相色谱分离也被证明是一种可行的方法,用于异构体的歧视。尽管LC未完全分离2-和7-异构体,但发现可以使用其产物离子光谱区分它们,因为2-异构体产生因乙烯胺损失而形成的m/z 132碎片离子,而7-异构体通过甲胺损失形成m/z 158。在2-API的合成中,在环化反应中形成了一种新型三环副产物,其中反应溶剂四氢呋喃被掺入分子中。
In 2012, 5-(2-aminopropyl)indole (5-API, 5-IT) was reported by Norwegian authorities to the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) via the Early Warning System (EWS). The 3- isomer, 3-(2-aminopropyl)indole (3-API, AMT, alpha-methyltryptamine), has been available on the recreational drugs market for a somewhat longer time, having first been reported to the EMCDDA by Finnish authorities in 2001. Both isomers are available from online vendors of 'legal highs'. Recently, three forensic drug cases (two tablets and one powder) were presented for routine analysis and the active constituent was tentatively identified as an API isomer. The six positional isomers (2-, 3-, 4-, 5-, 6- and 7-(2-aminopropyl)indoles) were synthesized and analyses by a combination gas chromatography-mass spectrometry (GC-MS), and liquid chromatography-mass spectrometry (LC-MS) showed that these could be readily discriminated thus facilitating the identification of 3-API in the tablets and 5-API in the powder. With exception of 5- and 6-APIs, which co-eluted, it was found possible to separate the isomers by GC without derivatization. LC separation also proved to be a feasible method for the discrimination of the isomers. Although the 2- and 7- isomers were not fully resolved by LC, it was found possible to distinguish them using their product ion spectra as the 2- isomer produced the m/z 132 fragment ion formed by loss of vinylamine, whereas the 7- isomer formed m/z 158 through loss of methylamine. In the synthesis 2-API, a novel tricyclic by-product was formed in an annulation reaction where the reaction solvent, tetrahydrofuran, was incorporated into the molecule.
DOI: 10.1016/j.tetlet.2006.12.136
发表时间: 2007-02
影响因子: 1.8
作者:
H. F. Russell;J. Bremner;Jennifer Bushelle-Edghill;M. Lewis;Stacey R. Thomas;F. Bates
通讯作者: H. F. Russell;J. Bremner;Jennifer Bushelle-Edghill;M. Lewis;Stacey R. Thomas;F. Bates