Electrochemical and spectroscopic characterisation of amphetamine-like drugs: Application to the screening of 3,4-methylenedioxymethamphetamine (MDMA) and its synthetic precursors

• Published in: Analytica chimica acta Vol. 596; no. 2; pp. 231 - 241
• Main Authors: Milhazes, Nuno, Martins, Pedro, Uriarte, Eugenio, Garrido, Jorge, Calheiros, Rita, Marques, M. Paula M., Borges, Fernanda
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 23.07.2007; Elsevier
• Subjects: 3,4-Methylenedioxymethamphetamine; Amphetamines - analysis; Amphetamines - chemistry; Analytical chemistry; Chemistry; Chromatography, High Pressure Liquid - methods; Density functional theory calculations; Electrochemical methods; Electrochemistry; Exact sciences and technology; N-Methyl-3,4-methylenedioxyamphetamine - analysis; N-Methyl-3,4-methylenedioxyamphetamine - chemistry; Prodrugs - analysis; Prodrugs - chemistry; Raman spectroscopy; Spectrometric and optical methods; Spectrum Analysis, Raman - methods; Synthesis; Voltammetry; Voltammetry; 3,4-Methylenedioxymethamphetamine; Synthesis; Raman spectroscopy; Density functional theory calculations; Drug; Chemical analysis; Electrochemical method; Aldehyde; Nitrogen; Precursor; Lead; Amfetamine; Raman spectrometry; Drug of abuse; Methylation; Primary amine
• ISSN: 0003-2670; 1873-4324
• DOI: 10.1016/j.aca.2007.06.027

A complete physicochemical characterisation of MDMA and its synthetic precursors MDA, 3,4-methylenedioxybenzaldehyde (piperonal) and 3,4-methylenedioxy-β-methyl-β-nitrostyrene was carried out through voltammetric assays and Raman spectroscopy combined with theoretical (DFT) calculations. The former provided important analytical redox data, concluding that the oxidative mechanism of the N-demethylation of MDMA involves the removal of an electron from the amino-nitrogen atom, leading to the formation of a primary amine and an aldehyde. The vibrational spectroscopic experiments enable to afford a rapid and reliable detection of this type of compounds, since they yield characteristic spectral patterns that lead to an unequivocal identification. Moreover, the rational synthesis of the drug of abuse 3,4-methylenedioxymethamphetamine (MDMA or “ecstasy”) from one of its most relevant precursors 3,4-methylene-dioxyamphetamine (MDA), is reported. In addition, several approaches for the N-methylation of MDA, a limiting synthetic step, were attempted and the overall yields compared.