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A chiral high performance liquid chromatography method was developed for the resolution of the enantiomers of two new β-aminoalcohols, isamoltane and enciprazine. The separation of the enantiomers was accomplished, without any derivatization, on a chiral column containing 3,5-dimethylphenylcarbamate of cellulose (Chiralcel OD) as chiral selector. The effects of diethylamine, organic modifiers (ethanol and 2-propanol) and temperature were studied. The α and Rs values of isamoltane and enciprazine ranged, respectively, from 1.25 to 2.03 and from 0.80 to 5.16. The optimized conditions were used for a semipreparative chromatographic separation to determine the elution order of the enantiomers.