FIRST PREPARATIVE ENANTIOMER RESOLUTION OF PIRLINDOLE, A POTENT ANTIDEPRESSANT DRUG

Pirlindole is an antidepressant drug. It acts principally as reversibl e inhibitor of monoamine oxidase-a (RIMA) and appears relatively poten t in comparison with reference drugs. Pirlindole possesses stereogenic center but is generally used as racemate. In this work, the first pre parative resolution of its enantiomeric couple is described. Whereas s elective crystallization of salts of chiral acid failed, two asymmetri c synthetic pathways were also examined; however, without success. Fin ally separation and isolation of enantiomers of pirlindole was complet ed by using the derivatization method coupled with preparative HPLC. O ptical purity of each isomer was determined by chiral HPLC. The specif ic rotation of each antipode was also determined.