Biomedical Chromatography 1991-01-01

Enantiomeric analysis of phenylpropanolamine in plasma via resolution of dinitrophenylurea derivatives on a high performance liquid chromatographic chiral stationary phase.

T D Doyle, C A Brunner, J A Vick

Index: Biomed. Chromatogr. 5(1) , 43-6, (1991)

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Abstract

Racemic phenylpropanolamine was resolved on a high performance liquid chromatographic (HPLC) chiral stationary phase (CSP) as the 3,5-dinitrophenyl ureide derivative. The CSP was prepared by a simple in situ procedure in which (R)-(1-naphthyl)ethyl isocyanate was bound to aminopropyl silanized silica through a urea linkage. The enantiomeric ureides were prepared by a room-temperature, 60-second procedure, accomplishing simultaneous extraction and derivatization and utilizing achiral 3,5-dinitrophenyl isocyanate as reagent. Baseline resolution was readily achieved under normal phase conditions, with a separation factor (alpha) of 1.16 and a resolution factor (RS) of 2.2. Elution was complete within 10 min. A limit of detection, by UV at 235 nm, of 250 pg per isomer was established. Feasibility of the procedure for plasma determinations was demonstrated by assay of samples from a canine subject.