PMID- 17631101
OWN - NLM
STAT- MEDLINE
DCOM- 20070907
LR  - 20131121
IS  - 1873-4324 (Electronic)
IS  - 0003-2670 (Linking)
VI  - 596
IP  - 2
DP  - 2007 Jul 23
TI  - Electrochemical and spectroscopic characterisation of amphetamine-like drugs: 
      application to the screening of 3,4-methylenedioxymethamphetamine (MDMA) and its 
      synthetic precursors.
PG  - 231-41
AB  - 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.
FAU - Milhazes, Nuno
AU  - Milhazes N
AD  - CEQOFFUP, Faculdade de Farmacia, Universidade do Porto, Portugal.
FAU - Martins, Pedro
AU  - Martins P
FAU - Uriarte, Eugenio
AU  - Uriarte E
FAU - Garrido, Jorge
AU  - Garrido J
FAU - Calheiros, Rita
AU  - Calheiros R
FAU - Marques, M Paula M
AU  - Marques MP
FAU - Borges, Fernanda
AU  - Borges F
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20070619
PL  - Netherlands
TA  - Anal Chim Acta
JT  - Analytica chimica acta
JID - 0370534
RN  - 0 (Amphetamines)
RN  - 0 (Prodrugs)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
SB  - IM
MH  - Amphetamines/analysis/*chemistry
MH  - Chromatography, High Pressure Liquid/methods
MH  - Electrochemistry
MH  - N-Methyl-3,4-methylenedioxyamphetamine/analysis/*chemistry
MH  - Prodrugs/analysis/*chemistry
MH  - Spectrum Analysis, Raman/*methods
EDAT- 2007/07/17 09:00
MHDA- 2007/09/08 09:00
CRDT- 2007/07/17 09:00
PHST- 2007/01/05 00:00 [received]
PHST- 2007/06/05 00:00 [revised]
PHST- 2007/06/14 00:00 [accepted]
PHST- 2007/07/17 09:00 [pubmed]
PHST- 2007/09/08 09:00 [medline]
PHST- 2007/07/17 09:00 [entrez]
AID - S0003-2670(07)01060-4 [pii]
AID - 10.1016/j.aca.2007.06.027 [doi]
PST - ppublish
SO  - Anal Chim Acta. 2007 Jul 23;596(2):231-41. doi: 10.1016/j.aca.2007.06.027. Epub 
      2007 Jun 19.