We present an ionic liquid (IL) approach towards a dual functional liquid salt form of aspirin using different pharmaceutically active cations composed of antibacterials, analgesics, local anesthetics, and antiarrhythmic drugs in combination with acetylsalicylic acid or its metabolite salicylic acid and discuss stability of these ILs in comparison to solid salts. Several low-melting or liquid salts of salicylic acid with dual functionality and promising properties were isolated and characterized; however, although such ILs with aspirin could be prepared, they suffer from limited stability and slowly decompose into the corresponding salicylate ILs when exposed to moisture.

We present evidence of hydrogen bond formation, not salt formation, as the driving force in the liquefaction of a solid pharmaceutical in the form of a neutral acid–base complex, as exemplified by the liquid formed from a mixture of the local anesthetic lidocaine with fatty acids; these complexes exist at the boundary between simple eutectics and partially ionised ionic liquids.

Pharmaceutically active compounds in ionic liquid form immobilized onto mesoporous silica are stable, easily handled solids, with fast and complete release from the carrier material when placed into an aqueous environment. Depending on specific ion-surface interactions, they may also exhibit improved thermal stability when compared to the non-adsorbed compounds.