Identification of common impurities present in the synthetic routes leading to 4-methylthioamphetamine (4-MTA). Part II: Reductive amination and nitropropene route

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• 作者：Dariusz B艂achut^a ; ¹ ; ^{blachutd@op.pl} ; Joanna Szawka艂o^b ; Zbigniew Czarnocki^b
• 关键词：Nitropropene route ; Synthetic impurities ; Amphetamine analogues
• 刊名：Forensic Science International
• 出版年：2012
• 期刊代码：104_03790738
• 类别：med
• 出版时间：10 April, 2012
• 卷：217
• 期：1-3
• 页码：60-70
• 文件大小：1071 K

摘要

In this paper the by-products arising during the synthesis of 4-methylthioamphetamine (4-MTA) by LiAlH₄ reduction of 1-(4-methylthiophenyl)-2-nitropropene (nitropropene route) and reductive amination of 4-methylthiophenyl-2-propanone in the presence of NaCNBH₄ are investigated. The identification of 4-methylthio derivatives of N-(尾-phenylisopropyl)benzaldimine, 4-methylthio derivative of N-(尾-phenylisopropyl)benzyl methyl ketimine, 1-(4-methylthiophenyl)-N-(4-methylthiobenzyl)-2-propanamine, (RS) and (SS/RR)-N,N-di-[尾-(4-methylthiophenyl)isopropyl]amine, 4-methylthiobenzyl ether and methylthiobenzoic acid methyl ester as most prominent impurities in crude 4-MTA synthesised by reductive amination of 4-methylthiophenyl-2-propanone, is reported. Methylthio derivatives of 2-methyl-3-phenylaziridine, 2-benzylaziridine, and 4-methylthio derivative of BMK oxime as route-specific markers of nitropropene route leading to 4-MTA, were also characterized. The identity of these compounds was confirmed by their independent synthesis.