环取代apan和MAPA类似物合成ATS的杂质谱分析。

IF 2.7 3区 医学 Q2 BIOCHEMICAL RESEARCH METHODS
Deanna Langone, Ben Painter, Clark Nash, Janneke W Hulshof, Sander Oldenhof, Martin R Johnston, K Paul Kirkbride
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引用次数: 0

摘要

合成安非他明类兴奋剂的设计前体对执法构成了重大挑战。前体apan (α-苯基乙酰乙腈)和MAPA(甲基α-乙酰苯基乙酸酯)在过去十年中开始流行,此后一直受到限制。最近,一种用于合成MDMA(3,4-亚甲基二氧基甲基苯丙胺)的MAPA的环取代类似物被发现,突出了这些设计前体的取代类似物被滥用的可能性。前人的研究已经对由apan和MAPA合成的甲基苯丙胺的杂质谱进行了表征。本研究表征了由apan和MAPA环取代类似物合成的MDMA和PMMA(对甲氧基甲基苯丙胺)的杂质谱。此外,对apan和MAPA的对甲基和对氟类似物转化为P2P类似物的副产物进行了研究。以3,4-亚甲二氧基取代的MAPA(甲基α-乙酰基-[3,4-亚甲二氧基]乙酸酯,MAMDPA)为原料,经三氰硼氢化钠还原胺化、氧化铂和甲胺加氢合成MDMA。在还原胺化合成的MDMA中检测到四种源自MAMDPA的杂质,它们都是MAPA合成的甲基苯丙胺中检测到的杂质的3,4-亚甲基二氧基类似物。通过加氢途径合成MDMA只产生一种特征杂质,由于其在酸性条件下不稳定,不太可能存在于秘密盐酸MDMA样品中。以甲氧基取代的apan (α-对甲氧基苯基乙酰乙腈,APMPAAN)为原料,采用氰硼氢化钠还原胺化法制备了PMMA。鉴定出五种杂质来源于APMPAAN,其中两种杂质被认为是APMPAAN在PMMA合成中最可靠的标记物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Impurity Profiling of ATS Synthesized From Ring-Substituted APAAN and MAPA Analogs.

Designer precursors for the synthesis of amphetamine-type stimulants pose a significant challenge to law enforcement. The precursors APAAN (α-phenylacetoacetonitrile) and MAPA (methyl α-acetylphenylacetate) became popular in the previous decade and have since been restricted. Recently, a ring-substituted analog of MAPA used for the synthesis of MDMA (3,4-methylenedioxymethamphetamine) was detected, highlighting the potential for criminal misuse of substituted analogs of these designer precursors. Previous research has characterized the impurity profiles of methamphetamine synthesized from APAAN and MAPA. In this study, the impurity profiles of MDMA and PMMA (p-methoxymethamphetamine) synthesized from ring-substituted analogs of APAAN and MAPA were characterized. In addition, byproducts forming from the conversion of p-methyl and p-fluoro analogs of APAAN and MAPA into analogs of P2P were investigated. MDMA was synthesized from 3,4-methylenedioxy-substituted MAPA (methyl α-acetyl-[3,4-methylenedioxyphenyl]acetate, MAMDPA) via sodium cyanoborohydride reductive amination and hydrogenation with platinum oxide and methylamine. Four impurities originating from MAMDPA were detected in MDMA synthesized via reductive amination, all of which are 3,4-methylenedioxy analogs of the impurities detected in methamphetamine synthesized from MAPA. Synthesis of MDMA via the hydrogenation route only produced one characteristic impurity, which, due to its instability under acidic conditions, is not likely to be present in clandestine MDMA hydrochloride samples. PMMA was synthesized via sodium cyanoborohydride reductive amination of MeO-P2P produced from methoxyl-substituted APAAN (α-p-methoxyphenylacetoacetonitrile, APMPAAN). Five impurities were identified as originating from APMPAAN, two of which are proposed to be the most reliable markers for the use of APMPAAN in the synthesis of PMMA.

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来源期刊
Drug Testing and Analysis
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.
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