Environmentally friendly expeditious one-pot electrochemical synthesis of bis-catechol-thioether metabolites of ecstasy: in vitro neurotoxic effects in the rat hippocampus - Archive ouverte HAL
Article Dans Une Revue International Journal of Electrochemical Science Année : 2008

Environmentally friendly expeditious one-pot electrochemical synthesis of bis-catechol-thioether metabolites of ecstasy: in vitro neurotoxic effects in the rat hippocampus

Résumé

A straightforward one-pot electrochemical synthesis of bis-catechol-thioether metabolites of MDMA (ecstasy), 2,5-bis(glutathion-S-yl)-N-methyl--methyldopamine and 2,5-bis(N-acetylcystein-S-yl)-N-methyl--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--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 dicussed through their ability to elicit necrosis and apoptosis on rat hippocampal pyramidal neurons.
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hal-03138868 , version 1 (11-02-2021)

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  • HAL Id : hal-03138868 , version 1

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Anne Felim, Anne Neudorffer, François P. Monnet, Martine Largeron. Environmentally friendly expeditious one-pot electrochemical synthesis of bis-catechol-thioether metabolites of ecstasy: in vitro neurotoxic effects in the rat hippocampus. International Journal of Electrochemical Science, 2008, 3 (2), pp.266-281. ⟨hal-03138868⟩
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