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Monoamine Oxidase Inhibitory Properties of Optical Isomers and N -substituted Derivatives of 4-methylthioamphetamine

2003; Taylor & Francis; Volume: 18; Issue: 4 Linguagem: Inglês

10.1080/1475636031000118437

1475-6374

Claudio Hurtado‐Guzmán, Angélica Fierro, Patricio Iturriaga‐Vásquez, Silvia Sepúlveda‐Boza, Bruce K. Cassels, Miguel Reyes‐Parada,

Neurotransmitter Receptor Influence on Behavior

(+/-)-4-Methylthioamphetamine (MTA) was resolved into its enantiomers, and a series of N-alkyl derivatives of the parent compound, as well as its alpha-ethyl analogue, were prepared. The monoamine oxidase (MAO) inhibitory properties of these substances were evaluated in vitro, using a crude rat brain mitochondrial suspension as the source of enzyme. All compounds produced a selective, reversible and concentration-related inhibition of MAO-A. (+)-MTA proved to be the most potent inhibitor studied, while all the other derivatives were less active than the parent compound, with (-)-MTA being about 18 times less potent than the (+) isomer. The analysis of structure-activity relationships indicates that the introduction of alkyl substituents on the amino group of MTA leads to a reduction in the potency of the derivatives as MAO-A inhibitors, an effect which increases with the size of the substituent.