Steric influence on inhibition of monoamine oxidase forms by 2,3-dichloro-alpha-methylbenzylamine.
The (+) isomer of 2,3-dichloro-alpha-methylbenzylamine inhibited the oxidation of serotonin (a substrate of type A MAO) by rat brain mitochondrial monoamine oxidase (MAO) more effectively than it inhibited the oxidation of phenylethylamine (a substrate for type B MAO). In contrast, the (-) isomer inhibited phenylethylamine oxidation more than it inhibited serotonin oxidation. These apparently are the first pair of stereoisomers observed to have opposite selectivity as inhibitors of types A and B MAO.
D000588:Amines / Q000494:pharmacology*; D000818:Animals; D001596:Benzylamines / Q000494:pharmacology*; D001921:Brain / Q000201:enzymology / Q000648:ultrastructure; D066298:In Vitro Techniques; D007700:Kinetics; D008928:Mitochondria / Q000201:enzymology; D008996:Monoamine Oxidase Inhibitors; D010627:Phenethylamines / Q000378:metabolism; D051381:Rats; D012701:Serotonin / Q000378:metabolism; D013237:Stereoisomerism
D000588:Amines; D001596:Benzylamines; D008996:Monoamine Oxidase Inhibitors; D010627:Phenethylamines; D012701:Serotonin; C002569:2,3-dichloro-alpha-methylbenzylamine