Short communication, Note
https://doi.org/10.2478/10004-1254-61-2010-1937
Toxicological Methods for Tracing Drug Abuse: Chromatographic, Spectroscopic and Biological Characterisation of Ecstasy Derivatives
Hafid Belhadj-Tahar
; Centre Anti-Poisons, CHU Purpan, Toulouse, France
Pierre Payoux
; EA3033, Faculté de Médecine Université Paul Sabatier, Toulouse, France
Mathieu Tafani
; EA3033, Faculté de Médecine Université Paul Sabatier, Toulouse, France
Yvon Coulais
; EA3033, Faculté de Médecine Université Paul Sabatier, Toulouse, France
Serge Calet
; Laboratoire Holis Technologies, Toulouse, France
Azzedine Bousseksou
; CNRS, Laboratoire de Chimie de Coordination4, Toulouse, France
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 unidentifi ed 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 coeffi cient, (ii) binding to plasmatic proteins (Fbp), and (iii) membrane adsorption. Chemical structure was determined with antibody fl uorescence polarisation immunoassay (FPIA). This study showed the presence of solid impurities, particularly of a neurotoxic compound of Al3+ in the fi nal products. FPIA identifi ed 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.
Keywords
IR; MDA; MDMA; MDNP; NMR; Raman; toxicology
Hrčak ID:
49018
URI
Publication date:
17.3.2010.
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