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

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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 (α) 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.

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