Environmentally Friendly Expeditious One-Pot Electrochemical Synthesis of Bis-Catechol-Thioether Metabolites of Ecstasy: in vitro Neurotoxic Effects in the Rat Hippocampus
Anne Felim, Anne Neudörffer, François P. Monnet, Martine Largeron
International Journal of Electrochemical Science February 9, 2026 DOI: 10.1016/s1452-3981(23)15452-6 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Population | Rat hippocampal neurons |
| Intervention | 5-bis(glutathion-S-yl)-N-methyl-α-methyldopamine and 2 |
| Topics | MDMA |
| Keywords | Anodic oxidation In vitro neurotoxicity Quinone Thioether metabolites |
| Key points | The electrochemical synthesis produces bis-catechol-thioether metabolites of MDMA in high purity, and the authors propose that these bis-conjugates may contribute to MDMA's neurotoxicity by inducing necrosis and apoptosis in rat hippocampal neurons. |
Abstract
A straightforward one-pot electrochemical synthesis of bis-catechol-thioether metabolites of MDMA (ecstasy), 2,5-bis(glutathion-S-yl)-N-methyl-α-methyldopamine and 2,5-bis(N-acetylcystein-S-yl)-N-methyl-α-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-α-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.
Comparable studies
Other theoretical and historical papers on MDMA, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Differences Between the Mechanism of Action of MDMA, MBDB, and the Classic Hallucinogens. Identification of a New Therapeutic Class: Entactogens | 1986 | Theoretical or philosophical paper | |
| The Background and Chemistry of MDMA | 1986 | Historical analysis | |
| The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents* Original documents in Merck's historical archive in Darmstadt, Germany, years 1900–1960 | 2006 | Historical analysis | |
| Distinct neural mechanisms for the prosocial and rewarding properties of MDMA | 2019 | Theoretical or philosophical paper | |
| How could MDMA (ecstasy) help anxiety disorders? A neurobiological rationale | 2009 | Theoretical or philosophical paper |
Citations in the library
Cited by 4
- Evaluation of the Ecstasy influence on tramadol and its main metabolite plasma concentration in rats Drug Metabolism and Personalized Therapy January 26, 2017
- Synthesis and Neurotoxicity Profile of 2,4,5-Trihydroxymethamphetamine and Its 6-(N-Acetylcystein-S-yl) Conjugate Chemical Research in Toxicology May 10, 2011
- Synthesis and in vitro cytotoxicity profile of the R-enantiomer of 3,4-dihydroxymethamphetamine (R-(-)-HHMA): comparison with related catecholamines. Chemical Research in Toxicology January 2010
- [Metabolites of ecstasy and cytotoxicity effects]. Annales pharmaceutiques francaises March 2009
Cites 12
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- Pathology of deaths associated with "ecstasy" and "eve" misuse. Journal of Clinical Pathology February 1, 1996
- MDMA (Ecstasy) and the Rave: A Review Pediatrics October 1, 1997
- Stereospecific Analysis and Enantiomeric Disposition of 3,4-Methylenedioxymethamphetamine (Ecstasy) in Humans Clinical Chemistry July 1, 1999
- The Role of Metabolism in 3,4-(±)-Methylenedioxyamphetamine and 3,4-(±)-Methylenedioxymethamphetamine (Ecstasy) toxicity Therapeutic Drug Monitoring March 19, 2004
and 7 more in the library