1. Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted α-alkylthioamphetamines
- Author
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Cloonan, Suzanne M., Keating, John J., Corrigan, Desmond, O’Brien, John E., Kavanagh, Pierce V., Williams, D. Clive, and Meegan, Mary J.
- Subjects
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ORGANIC synthesis , *TOXICOLOGY , *AMINES , *MOLECULAR recognition , *DRUG abuse , *PYRIDINE , *NUCLEAR magnetic resonance , *CELL-mediated cytotoxicity , *DOPAMINERGIC neurons , *AMPHETAMINES - Abstract
Abstract: 4-Methylthioamphetamine (4-MTA) is recognised as a 3,4-methylenedioxymethamphetamine (MDMA)-like drug of abuse. Such amphetamine-type drugs often contain byproducts of uncontrolled, illegal clandestine synthetic processes. We report the isolation and structural identification of a number of novel pyridines, dihydropyridone and N,N-di(1-aryl-2-propyl) amines as route-specific byproducts associated with clandestine synthesis of 4-MTA and related amphetamines. We report the in vitro cytotoxicity of 4-MTA, its synthesis byproducts together with some structurally related sulfur substituted α-alkyl phenethylamines in cell lines overexpressing human monoamine transporters as well as in a primary neuronal cell line model and a dopaminergic neuroblastoma cell line. 4-MTA along with a number of other structurally related amphetamine derivatives and synthetic impurities were found to be cytotoxic to these cells within pharmacologically defined concentrations implying that 4-MTA is a cytotoxic agent in vitro and therefore might have the potential to be a neurotoxic agent in vivo. [Copyright &y& Elsevier]
- Published
- 2010
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