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Papaverine hydrochloride loaded gels, films and electrospun fibers were prepared for buccal drug delivery with the aim of improving the oral bioavailability of the crystalline drug, which can be achieved by the increased solubility and by the circumvention of the intensive first pass metabolism. The water soluble hydroxypropyl cellulose (HPC) was chosen as a mucoadhesive polymer. In order to improve the electrospinnability of HPC, the similarly mucoadhesive poly(vinyl alcohol) (PVA) was used. Since the drying of gels is of decisive role in either the formation of drug-loaded cast films or electrospun fibers, a real time ortho-positronium (o-Ps) tracking of gels was applied in order to obtain information about the supramolecular changes of the drying-induced gel-film transition. An anomalous increase of o-Ps lifetime value in the gel-film transition region was observed which refers to the remaining intramolecularly bound water in the drug-loaded polymeric gel matrix. The latter could provide information about the characteristics of polymer-water interactions in the phase transition, consequently the storage stability of the formulated solid system.