2009
DOI: 10.1124/dmd.108.026393
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Neurotoxic Thioether Adducts of 3,4-Methylenedioxymethamphetamine Identified in Human Urine After Ecstasy Ingestion

Abstract: 3,4-Methylenedioxymethamphetamine (MDMA, Ecstasy) is a psychostimulant widely abused among young people. MDMA exhibits distinct pharmacological properties, collectively described as entactogenic, which differentiate it from classic amphetamines (Nichols, 1986). MDMA produces acute and long-term serotonergic neurotoxicity in rodents, primates, and, possibly, in humans, with the severity of toxicity dependent on the dose and frequency of administration (Green et al., 2003). Such neurotoxicity is demonstrated by … Show more

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Cited by 32 publications
(34 citation statements)
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“…No significant differences were observed in 5-HIAA levels in controls and rats treated with 5-NAC-HHMA groups, with or without fluoxetine pretreatment (data not shown). (Capela et al, 2009;Perfetti et al, 2009). This is the first study to assess the relationship between pharmacokinetic parameters (C max and AUC) of MDMA and its major metabolites (HHMA, HMMA, and MDA) and 5-HT neurotoxic effects in the same animal.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…No significant differences were observed in 5-HIAA levels in controls and rats treated with 5-NAC-HHMA groups, with or without fluoxetine pretreatment (data not shown). (Capela et al, 2009;Perfetti et al, 2009). This is the first study to assess the relationship between pharmacokinetic parameters (C max and AUC) of MDMA and its major metabolites (HHMA, HMMA, and MDA) and 5-HT neurotoxic effects in the same animal.…”
Section: Resultsmentioning
confidence: 99%
“…One hypothesis that has recently drawn considerable attention is that a drug metabolite is involved (Capela et al, 2009;Perfetti et al, 2009). Over the years, various metabolites of MDMA and related drugs have been evaluated for possible 5-HT neurotoxic activity (Fig.…”
mentioning
confidence: 99%
“…(Scheme 1). [12] It must be noted that body disposition of MDMA is subjected to selective enantiomeric metabolism. [13] Although the methods reported herein would allow for the preparation of enantiomerically pure compounds, it was considered unnecessary for this preliminary study of the pharmacological activity of the synthesized compounds.…”
Section: Introductionmentioning
confidence: 99%
“…These thioether compounds retain the ability to redox cycle and are toxic to 5-HT neurons. In fact, they are more toxic than MDMA itself (Monks et al, 2004;Ferreira et al, 2013) and have also been detected in vivo after MDMA exposure (de la Torre and Farre, 2004;Perfetti et al, 2009). Nonetheless, DA remains an important factor also in MDMA-induced 5-HT toxicity (Stone et al, 1988;Schmidt et al, 1990;Shankaran et al, 1999;Falk et al, 2002;Breier et al, 2006).…”
Section: Action Of Substituted Amphetamines and Cathinonesmentioning
confidence: 99%