Like methylcylohexanol, rimantadine can bind the cyclodextrins in either a primary or secondary orientation (Figure ), where secondary binding means that its amine functionality is at the larger secondary opening of cyclodextrin, and primary binding means the amine is at the smaller primary opening. The near-symmetry of rimantadine can make it difficult to distinguish among its proton peaks and thus to determine its binding orientation. However, on binding to β-CD, the CH (H3, H5, H7, H9) and CH2 (C4, C6, C8, C10) peaks shift to give two separate quartets, with the CH groups consistently more deshielded . This small difference makes it possible to determine binding through NOESY interactions with the host's protons. Table summarizes the key NOEs observed between the present hosts and rimantidine, noting as well the implications of these data for the bound conformations. Cases of primary and secondary binding are observed across the different derivatives, and, unlike methylcyclohexanol, there are no cases where NOEs corresponding to both orientations were observed. For MGLab 9, no intermolecular NOEs were observed, and for MGLab 35, the large substituent led to overlapping proton peaks with rimantadine, making it hard to determine the binding orientation. There is no clear correlation between the orientational preferences of rimantidine and those of methylcylohexanol across these hosts.