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Abstract: A uniform-sized molecularly imprinted polymer for (S)- propranolol has been prepared by a multi-step swelling and thermal polymerization method using methacrylic acid (MAA) and ethylene glycol dimethacrylate (EDMA) as a host functional monomer and cross-linker: respectively. The obtained (S)- propranolol imprinted MAA-EDMA materials were evaluated using aqueous-rich eluents by HPLC. The (S)-propranolol imprinted MAA-EDMA materials had specific recognition for (S)-propranolol and moderate recognition for some structurally related beta- adrenergic antagonists (especially, pindolol and alprenolol), but had no recognition for other basic compounds, and neutral and acidic compounds. Enantioseparations of propranolol and some structurally related S-adrenergic antagonists were attained with the imprinted MAA-EDMA materials. Hydrophobic interaction of the naphthyloxy and isopropyl groups of propranolol, and ionic interaction of the isopropylamino group of propranolol with the (S)-propranolol imprinted MAA-EDMA materials could play an important role in enantioselective recognition of propranolol. (C) 2000 Elsevier Science B.V. All rights reserved