Synthesis and Cyclic Voltammetry Studies of 3,4-Methylenedioxymethamphetamine (MDMA) Human Metabolites

Autor:	Luísa M. Ferreira, João Paulo Capela, Carla Macedo, Maria de Lourdes Bastos, Félix Carvalho, Eduarda Fernandes, Ana M. Lobo, Paula S. Branco
Rok vydání:	2007
Předmět:	Catechol Stereochemistry Health Toxicology and Mutagenesis Neurotoxicity MDMA Toxicology medicine.disease Chemical synthesis chemistry.chemical_compound chemistry mental disorders Toxicity medicine Cyclic voltammetry Voltammetry psychological phenomena and processes Drug metabolism medicine.drug
Zdroj:	JOURNAL OF HEALTH SCIENCE. 53:31-42
ISSN:	1347-5207 1344-9702
Popis:	3,4-Methylenedioxymethamphetamine (MDMA or “Ecstasy”) is a widely abused, psychoactive recreational drug. There are growing evidences that the MDMA neurotoxic profile may be highly dependent on its hepatic metabolism. MDMA metabolism leads to the production o fh ighly reactive derivates, namely catechols, catechol thioethers, and quinones. In this study the electrochemical oxidation-reduction processes of MDMA human metabolites, obtained by chemical synthesis, were evaluated by cyclic voltammetry based on an electrochemical cell with a glassy carbon working electrode. The toxicity of α-methyldopamine (α-MeDA), N-methyl-αmethyldopamine (N-Me-α-MeDA) and 5-(glutathion-S-yl)-α-methyldopamine [5-(GSH)-α-MeDA] to rat cortical neurons was then correlated with their redox potential. The obtained dat ad emonstrate dt hat the lower oxidation potential observed for the catecholic thioether of α-MeDA correlate dw ith the higher toxicity of this adduct. This accounts for the use of voltammetry data in predicting the toxicity of MDMA metabolites.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b18e4bcdd094ae5021255da15180c29c https://doi.org/10.1248/jhs.53.31 Zobrazit plný text záznamu