Archives of toxicology
August 1, 2015
Ana Margarida Araújo, Félix Carvalho, Maria de Lourdes Bastos et al.
290 citations
Tryptamines are a broad class of hallucinogens that act primarily as agonists of the 5-HT2A receptor, producing profound changes in sensory perception, mood, and thought. Historically, natural tryptamines like psilocybin and DMT have been used in ritual contexts, but synthetic tryptamines such as AMT, 5-MeO-DMT, and 5-MeO-DIPT have recently emerged as recreational drugs, often sold as 'research chemicals' online. Reports of intoxication and deaths have raised international concern, though the lack of pharmacological and toxicological data hampers assessment of their public health harm. This review covers historical background, prevalence, patterns of use, legal status, chemistry, toxicokinetics, toxicodynamics, and physiological and toxicological effects in animals and humans.
Chemical Research in Toxicology
April 27, 2004
Márcia Carvalho, Fernando Remião, Nuno Milhazes et al.
77 citations
MDMA (ecstasy) and its major metabolite MDA did not directly damage heart cells from adult rats in the lab, but two further metabolites, N-Me-alpha-MeDA and alpha-MeDA, caused significant toxicity. These catechol metabolites triggered a loss of normal cell shape, depletion of the antioxidant glutathione, sustained increases in intracellular calcium, drops in ATP, and reduced activity of antioxidant enzymes. N-Me-alpha-MeDA was the most toxic. The findings suggest that MDMA must be metabolized into these catechol compounds for cardiotoxicity to occur in isolated heart cells.
JOURNAL OF HEALTH SCIENCE
January 1, 2007
Carla Macedo, Paula S. Branco, Luı́sa M. Ferreira et al.
36 citations
The neurotoxic effects of MDMA (Ecstasy) may depend heavily on how the body metabolizes the drug in the liver. Metabolism produces highly reactive compounds, including catechols, catechol thioethers, and quinones. Researchers used cyclic voltammetry to measure the electrochemical oxidation-reduction processes of chemically synthesized human MDMA metabolites. They then correlated the redox potentials of α-methyldopamine, N-methyl-α-methyldopamine, and 5-(glutathion-S-yl)-α-methyldopamine with their toxicity to rat cortical neurons. The data demonstrated that the lower oxidation potential of the catecholic thioether of α-MeDA correlated with its higher toxicity, supporting the use of voltammetry data to predict the toxicity of MDMA metabolites.