Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/45124
Title: Electrochemical and spectroscopic characterisation of amphetamine-like drugs: Application to the screening of 3,4-methylenedioxymethamphetamine (MDMA) and its synthetic precursors
Authors: Milhazes, Nuno 
Martins, Pedro 
Uriarte, Eugenio 
Garrido, Jorge 
Calheiros, Rita 
Marques, M. Paula M. 
Borges, Fernanda 
Keywords: Amphetamines; Chromatography, High Pressure Liquid; Electrochemistry; N-Methyl-3,4-methylenedioxyamphetamine; Prodrugs; Spectrum Analysis, Raman
Issue Date: 2007
Abstract: A complete physicochemical characterisation of MDMA and its synthetic precursors MDA, 3,4-methylenedioxybenzaldehyde (piperonal) and 3,4-methylenedioxy-beta-methyl-beta-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.
URI: http://hdl.handle.net/10316/45124
Other Identifiers: 10.1016/j.aca.2007.06.027
DOI: 10.1016/j.aca.2007.06.027
Rights: openAccess
Appears in Collections:FCTUC Ciências da Vida - Artigos em Revistas Internacionais

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