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N-Cyanomethyl-N-Methyl-1-(3′,4′-methylenedioxyphenyl)-2-propylamine: An MDMA Manufacturing By-Product

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Abstract: 

This paper describes the structural elucidation of a compound produced during the synthesis of 3,4-methylenedioxymethylamphetamine (MDMA) via the reductive amination of 3,4-methylenedioxyphenyl-2-propanone (3,4-MDP-2-P) with methylamine and sodium cyanoborohydride. The compound was isolated from MDMA by column chromatography, proton and carbon nuclear magnetic resonance spectroscopy, LC/mass spectrometry, and total synthesis were used to identify the compound as N-cyanomethyl-N-methyl-1-(3′,4′-methylenedioxyphenyl)-2-propylamine. This compound has been identified as a potential synthetic route marker for the reductive amination of 3,4-MDP-2-P with methylamine and sodium cyanoborohydride and as such it should prove valuable to forensic scientists engaged in profiling illicit drugs. Profiling MDMA can provide useful information to law enforcement agencies relating to synthetic route, precursor chemicals and reagents employed and may be used for comparative analyses of different drug seizures. This paper also describes the structural elucidation of the analogous methylamphetamine synthetic route marker compound, N-cyanomethyl-N-methyl-1-phenyl-2-propylamine, produced during the reductive amination of phenyl-2-propanone using methylamine and sodium cyanoborohydride.
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Keywords: 2-(dimethylamino)-2-methyl-3-(3′,4′-methylenedioxyphenyl)-propanenitrile; 3,4-methylenedioxymethylamphetamine; N-cyanomethyl-N-methyl-1-(3′,4′-methylenedioxyphenyl)-2-propylamine; N-cyanomethyl-N-methyl-1-phenyl-2-propylamine; chemical profiling; cyanoborohydride; forensic science; methylamphetamine

Document Type: Research Article

Affiliations: 1: National Measurement Institute, 1 Suakin St., Pymble, NSW, Australia. 2: School of Chemistry, University of Sydney, Sydney, NSW, Australia.

Publication date: September 1, 2008

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