Monoamine oxidase inhibitory properties of optical isomers and N-substituted derivatives of 4-methylthioamphetamine. Export

@article{citeulike:3771913, abstract = {(+/-)-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.}, author = {Hurtado-Guzm\'{a}n, C. and Fierro, A. and Iturriaga-V\'{a}squez, P. and Sep\'{u}lveda-Boza, S. and Cassels, B. K. and Reyes-Parada, M.}, citeulike-article-id = {3771913}, citeulike-linkout-0 = {http://view.ncbi.nlm.nih.gov/pubmed/14567549}, citeulike-linkout-1 = {http://www.hubmed.org/display.cgi?uids=14567549}, issn = {1475-6366}, journal = {Journal of enzyme inhibition and medicinal chemistry}, keywords = {4-mta, mao, maoi}, month = {August}, number = {4}, pages = {339--347}, posted-at = {2008-12-11 00:09:37}, priority = {2}, title = {Monoamine oxidase inhibitory properties of optical isomers and N-substituted derivatives of 4-methylthioamphetamine.}, url = {http://view.ncbi.nlm.nih.gov/pubmed/14567549}, volume = {18}, year = {2003} }

TY - JOUR ID - citeulike:3771913 L3 - citeulike-article-id:3771913 N2 - (+/-)-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. IS - 4 JF - Journal of enzyme inhibition and medicinal chemistry SN - 1475-6366 EP - 347 TI - Monoamine oxidase inhibitory properties of optical isomers and N-substituted derivatives of 4-methylthioamphetamine. VL - 18 SP - 339 KW - 4-mta KW - mao KW - maoi AU - Hurtado-Guzmán, C AU - Fierro, A AU - Iturriaga-Vásquez, P AU - Sepúlveda-Boza, S AU - Cassels, BK AU - Reyes-Parada, M PY - 2003/08// UR - http://view.ncbi.nlm.nih.gov/pubmed/14567549 ER -