This paper describes the rational design, generation and testing of a molecularly imprinted polymer specific for Ibuprofen. Ibuprofen is a member of the class of drugs termed non-steroidal anti-inflammatory drugs (NSAIDS). In the present study, Ibuprofen was used as a template molecule for the preparation of molecularly imprinted polymers. A MIP has been produced which is capable of recognising Ibuprofen in aqueous media. Furthermore, Ibuprofen can be selectively extracted from aqueous conditions by molecularly imprinted solid phase extraction (MISPE). Recoveries were typically high (> 80%) and good selectivity for Ibuprofen over structurally related analogues was seen. Moreover, the nature of the recognition between MIP and template has been investigated by NMR and molecular modelling to analyse whether or not it is possible to predict how well a given MIP will perform under set conditions. In addition, the physical characteristics of the MIP have been investigated including the particle size distribution on exposure of the MIP to different solvents. This has been related to the ability of the MIP to rebind Iboprofen under the same conditions. The data from the characterisation of the MIP has been used to further enhance the understanding of the nature of MIP recognition. (c) 2006 Elsevier B.V. All rights reserved.