Nicotine, a widely consumed, yet considered toxic, active pharmaceutical ingredient for recreational use, is known to rapidly deteriorate into unwanted and potentially harmful side products. Crystallization with salt formers transforms the unstable oil into solids with tunable properties. However, previously reported salts and co-crystals are not necessarily safe for human consumption, with several containing heavily halogenated coformers. When combined with malic acid, a generally recognized as safe (GRAS) compound, the four resulting crystalline solids exhibited melting points as high as 122 °C and spanned a range of ∼30 °C. The nicotine-based materials also possessed improved degradation properties. A detailed analysis of the crystal packing and thermodynamic properties provides context for the observed properties.

Many molecular drugs exist as liquid materials, however this state is not necessarily the most viable or stable means to store pharmaceuticals. Crystal engineering can be utilized to isolate these...

The use of crystal engineering to convert liquids into crystalline solids remains a powerful method for inhibiting undesired degradation pathways. When nicotine, a liquid sensitive to both light and air, is combined with the GRAS-listed compound, gentisic acid, the resulting crystalline solid, exhibits enhanced photo and thermal stability. Despite a modest ΔTm of 42.7 °C, the melting point of 155.9 °C for the nicotinium gentisate salt is the highest reported for nicotine-containing crystalline solids. An analysis of the crystal packing and thermodynamic properties provides context for the observed properties.

The organic salt (S)-nicotinium 2,6-dihydroxybenzoate undergoes reversible single crystal to single crystal phase transition at 104 K. The phase transition was monitored using temperature dependent single crystal X-ray diffraction and...

In the title 1:1 co-crystal [alternatively called bipyridine ethylene–p-vanillic acid (1/1)], C12H10N2·C8H8O4, the dihedral angle between the pyridine rings is 59.51 (5)°. In the crystal, the molecules are linked by O—H...N hydrogen bonds, generating [401] chains of alternating C12H10N2 and C8H8O4 molecules.