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Title: Synthesis and Cytotoxic Profile of 3,4-Methylenedioxymethamphetamine (“Ecstasy”) and Its Metabolites on Undifferentiated PC12 Cells: A Putative Structure−Toxicity Relationship
Authors: Milhazes, Nuno 
Cunha-Oliveira, Teresa 
Martins, Pedro 
Garrido, Jorge 
Oliveira, Catarina 
Rego, A. Cristina 
Borges, Fernanda 
Issue Date: Oct-2006
Publisher: American Chemical Society
Citation: Chemical Research in Toxicology. 19:10 (2006) 1294-1304
Abstract: The toxicological and redox profiles of MDMA and its major metabolites (MDA, α-methyldopamine, N-methyl-α-methyldopamine, 6-hydroxy-α-methyldopamine, 3-methoxy-α-methyldopamine) were studied to establish a structure-toxicity relationship and determine their individual contribution to cell death induction by apoptosis and/or necrosis. The results of the comparative toxicity study, using undifferentiated PC12 cells, strongly suggest that the metabolites possessing a catecholic group are more toxic to the cells than MDMA and metabolites with at least one protected phenolic group. Redox studies reveal that an oxidative mechanism seems to play an important role in metabolite cytotoxicity. Nuclear features of apoptosis and/or necrosis show that most of the metabolites, particularly N-methyl-α-methyldopamine, induce cell death by apoptosis, largely accompanied by necrotic features. No significant differences were found between MDMA and the metabolites, concerning overall characteristics of cell death. These results may be useful to ascertain the contribution of metabolism in MDMA neurotoxicity molecular mechanisms
ISSN: 0893-228X
DOI: 10.1021/tx060123i
Rights: openAccess
Appears in Collections:FMUC Medicina - Artigos em Revistas Internacionais

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