PMID- 20338868
OWN - NLM
STAT- MEDLINE
DCOM- 20100720
LR  - 20161205
IS  - 1848-6312 (Electronic)
IS  - 0004-1254 (Linking)
VI  - 61
IP  - 1
DP  - 2010 Mar
TI  - Toxicological methods for tracing drug abuse: chromatographic, spectroscopic and 
      biological characterisation of ecstasy derivatives.
PG  - 53-9
LID - 10.2478/10004-1254-61-2010-1937 [doi]
AB  - 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.
FAU - Belhadj-Tahar, Hafid
AU  - Belhadj-Tahar H
AD  - Centre Anti-Poisons, CHU Purpan, Toulouse, France. belhadj-tahar@afpremed.org
FAU - Payoux, Pierre
AU  - Payoux P
FAU - Tafani, Mathieu
AU  - Tafani M
FAU - Coulais, Yvon
AU  - Coulais Y
FAU - Calet, Serge
AU  - Calet S
FAU - Bousseksou, Azzedine
AU  - Bousseksou A
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - Croatia
TA  - Arh Hig Rada Toksikol
JT  - Arhiv za higijenu rada i toksikologiju
JID - 0373100
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
SB  - IM
MH  - Chromatography, High Pressure Liquid
MH  - Humans
MH  - Magnetic Resonance Spectroscopy
MH  - N-Methyl-3,4-methylenedioxyamphetamine/analogs & derivatives/*analysis/chemical 
      synthesis
MH  - Spectrophotometry, Infrared
MH  - Spectrum Analysis, Raman
MH  - Substance Abuse Detection/*methods
EDAT- 2010/03/27 06:00
MHDA- 2010/07/21 06:00
CRDT- 2010/03/27 06:00
PHST- 2010/03/27 06:00 [entrez]
PHST- 2010/03/27 06:00 [pubmed]
PHST- 2010/07/21 06:00 [medline]
AID - 9158884318282414 [pii]
AID - 10.2478/10004-1254-61-2010-1937 [doi]
PST - ppublish
SO  - Arh Hig Rada Toksikol. 2010 Mar;61(1):53-9. doi: 10.2478/10004-1254-61-2010-1937.