Lipid-based, base-triggerable systems will be useful for colon specific targeted delivery of drugs and pharmaceuticals. In light of this, a catanionic surfactant system, composed of O-lauroylethanolamine hydrochloride (OLEA center dot HCI) and sodium dodecyl sulfate (SDS), has been designed. The aggregates formed by near equimolar mixtures of OLEA center dot HCI SDS have shown lability at basic pH, indicating that the system may be useful for developing colon specific drug delivery system(s). Turbidimetric and isothermal titration calorimetric studies revealed that OLEA center dot HCl forms a 1:1 (mol/mol) complex with SDS. The three-dimensional structure of the equimolar OLEA SDS complex has been solved by single-crystal X-ray diffraction. Analysis of the molecular packing and intermolecular interactions in the crystal lattice revealed a hydrogen bonding belt in the headgroup region of the complex and dispersion interactions among the acyl chains as the main factors stabilizing the complex. These observations will be useful in understanding specific interactions between lipids in more complex systems, e.g., biomembranes.