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Abstract: Molecular imprint polymers (MIPs) are synthetic polymers capable of selectively binding a template molecule. In this work, the potential utility of MIP-based chromatographic sorbents for affinity screening of structurally similar compounds was investigated as alternatives to in vitro bioassays and biological targets bound to chromatographic supports. A group of structurally similar tricyclic antidepressant drugs and related compounds were used to simulate a combinatorial library. One of the antidepressants, nortriptyline (NOR), was selected as the template species. Using capillary HPLC columns packed with NOR-imprinted MIP particles, the simulated library was screened and the degree of selective interaction of each compound was determined. This correlated with each compound's affinity for the NOR binding site in the polymer. The results of the study revealed that library species which possess the major structural features of the template, specifically the ring structure and pendant secondary amine, were best "recognized" by the MIP, while the most structurally dissimilar compounds exhibited the least selective interaction. An investigation of the retention mechanism on these MIPs provided evidence that hydrogen bonding between the pendant amine group on the antidepressants and a methacrylic acid moiety on the polymer surface was critical in the molecular recognition process. (C) 2000 Elsevier Science B.V. All rights reserved