%0 Journal Article
%T Environmentally Friendly Expeditious One-Pot Electrochemical Synthesis of Bis-Catechol-Thioether Metabolites of Ecstasy: in vitro Neurotoxic Effects in the Rat Hippocampus
%A Anne Felim
%A Anne Neud£¿rffer
%A Fran£¿ois P. Monnet and Martine Largeron
%J International Journal of Electrochemical Science
%D 2008
%I Electrochemical Science Group
%X A straightforward one-pot electrochemical synthesis of bis-catechol-thioether metabolites of MDMA (ecstasy), 2,5-bis(glutathion-S-yl)-N-methyl-a-methyldopamine and 2,5-bis(N-acetylcystein-S-yl)-N-methyl-a-methyldopamine, in acceptable yields and high degree of purity (99%), is described under environmentally friendly conditions. The undeniable benefits of this method, which uses N-methyl-a-methyldopamine as the starting catechol, without the need to isolate the catechol-thioether mono-conjugate intermediate, include atom economy, as well as economies of time, resource management, and waste generation. Finally, the possible participation of the catechol-thioether bis-conjugates in the long-term neurotoxic effects of MDMA is discussed through their ability to elicit necrosis and apoptosis on rat hippocampal pyramidal neurons.
%K anodic oxidation
%K ecstasy
%K in vitro neurotoxicity
%K quinone
%K thioether metabolites
%U www.electrochemsci.org/papers/vol3/3030266.pdf