Trimipramine enantiomers

Ponder, G.W. Butram, S.L. Adams, A.G. Ramanathan, C.S. Stewart, J.T. Resolution of promethazine, ethopropazine, trimeprazine and trimipramine enantiomers on selected chiral stationary phases using high-performance liquid chromatography. J.Chromatogr.A, 1995, 692, 173-182... 

Ponder et al. [739] studied the retention of promethazine, ethopropazine, trimeprazine, and trimipramine enantiomers on nine different chiral phases... 

Trimipramine also is a dihydrodibenzazepine TCAthat differs structurally from imipramine in that the 5-propyl side chain is branched by a methyl group creating a chiral center (Fig. 21.15). Trimipramine is marketed as a racemic mixture. No data are available regarding the activity of the enantiomers. Apparently, branching the propyl side chain reduces affinity by 100 times for both 5-HT and NE transporters, but the selectivity ratio favors the 5-HT transporter. Although trimipramine has the weakest binding affinity for the monoamine... 

Eap CB, Bender S, Gastpar M, et al. Steady-state plasma levels of the enantiomers of trimipramine and of its metabolites in CYP2D6-, CYP2C19-, and CYP3A4/5-phenotyped patients. Ther Drug Monit 2000 22 209-214. 

C. B. Eap, Plasma levels of Trimipramine and metabolites in four patients determination of the enantiomer concentrations of the hydroxy metabolites. Therapeutic Drug Monitoring, 14(1992)380. 

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