<abstract xml:lang="en" xmlns="http://www.w3.org/1999/xhtml">Analysis often reveals variability in the composition of ecstasy pills from pure 3,4-methylenedioxymethamphetamine (MDMA) to mixtures of MDMA derivatives, amphetamine, and other unidentified substances. For a comprehensive toxicological analysis one needs to know all steps to MDMA synthesis which may originate impurities. The aim of this study was to synthesise and determine the chemical-physical and <italic>in vitro</italic> biological properties of a series of MDMA derivatives.3,4-methylendioxyphenyl-2-nitropropene (MDNP) was obtained by condensation of piperonal with an excess of nitroethane in the presence of ammonium acetate. MDNP was then reduced to methylenedioxyamphetamine (MDA) by LiAlH3. All compounds were analysed using HPLC and spectroscopic technique [Raman, nuclear magnetic resonance (NMR), or infrared (IR)] at all the steps of synthesis. In addition, we assessed the biological potentials of these compounds by measuring <italic>in vitro</italic> their (i) blood cell/whole blood partition coefficient, (ii) binding to plasmatic proteins (Fbp), and (iii) membrane adsorption. Chemical structure was determined with antibody fluorescence polarisation immunoassay (FPIA). This study showed the presence of solid impurities, particularly of a neurotoxic compound of Al3+ in the final products. FPIA identified the aminoethane group close to the substituted benzene ring, but did not detect the two major precursors of MDMA: MDNP and piperonal. Raman spectroscopy is an attractive alternative technique to characterise ecstasy pills and it can identify stereoisomeric forms such as <italic>cis</italic>-MDNP and <italic>trans</italic>-MDNP, which exhibit signals at 1650 cm-1 and 1300 cm-1, respectively.</abstract>

Analysis often reveals variability in the composition of ecstasy pills from pure 3,4-methylenedioxymethamphetamine (MDMA) to mixtures of MDMA derivatives, amphetamine, and other unidentified substances. For a comprehensive toxicological analysis one needs to know all steps to MDMA synthesis which may originate impurities. The aim of this study was to synthesise and determine the chemical-physical and in vitro biological properties of a series of MDMA derivatives.3,4-methylendioxyphenyl-2-nitropropene (MDNP) was obtained by condensation of piperonal with an excess of nitroethane in the presence of ammonium acetate. MDNP was then reduced to methylenedioxyamphetamine (MDA) by LiAlH3. All compounds were analysed using HPLC and spectroscopic technique [Raman, nuclear magnetic resonance (NMR), or infrared (IR)] at all the steps of synthesis. In addition, we assessed the biological potentials of these compounds by measuring in vitro their (i) blood cell/whole blood partition coefficient, (ii) binding to plasmatic proteins (Fbp), and (iii) membrane adsorption. Chemical structure was determined with antibody fluorescence polarisation immunoassay (FPIA). This study showed the presence of solid impurities, particularly of a neurotoxic compound of Al3+ in the final products. FPIA identified the aminoethane group close to the substituted benzene ring, but did not detect the two major precursors of MDMA: MDNP and piperonal. Raman spectroscopy is an attractive alternative technique to characterise ecstasy pills and it can identify stereoisomeric forms such as cis-MDNP and trans-MDNP, which exhibit signals at 1650 cm-1 and 1300 cm-1, respectively.

Toxicological Methods for Tracing Drug Abuse: Chromatographic, Spectroscopic and Biological Characterisation of Ecstasy Derivatives

Centre Anti-Poisons, CHU Purpan, Toulouse, France

Faculté de Médecine, Université Paul Sabatier, EA3033, Toulouse, France

Laboratoire Holis Technologies, Toulouse, France

CNRS, Laboratoire de Chimie de Coordination, Toulouse, France

Archives of Industrial Hygiene and Toxicology

Analysis often reveals variability in the composition of ecstasy pills from pure 3,4-methylenedioxymethamphetamine (MDMA) to mixtures of MDMA derivatives,...

Toxicological Methods for Tracing Drug Abuse: Chromatographic, Spectroscopic and Biological Characterisation of Ecstasy Derivatives

Published Online: Mar 25, 2010

Page range: 53 - 59

DOI: https://doi.org/10.2478/10004-1254-61-2010-1937

Keywords
IR, MDA, MDMA, MDNP, NMR, Ramanova spektroskopija, toksikologija

This content is open access.

Toxicological Methods for Tracing Drug Abuse: Chromatographic, Spectroscopic and Biological Characterisation of Ecstasy Derivatives

Published Online: Mar 25, 2010

Page range: 53 - 59

DOI: https://doi.org/10.2478/10004-1254-61-2010-1937

KeywordsIR, MDA, MDMA, MDNP, NMR, Ramanova spektroskopija, toksikologija

This content is open access.

Keywords
IR, MDA, MDMA, MDNP, NMR, Ramanova spektroskopija, toksikologija