Delavirdine mesylate was recrystallized from solution under a variety
of conditions. Seven crystal forms and a stable amorphous phase were i
solated from solution. Two of these crystal forms were polymorphic anh
ydrates: form XI (U-90152T) and form VIII (U-90152S). Two hydrates (fo
rms VI and XIV), an ethanol solvate (form VII), an acetonitrile solvat
e (form XIII), and a solvate from methanol/acetone (form XII) were als
o identified. Six additional phases were identified as the products of
solid-state transformations of the hydrated and solvated phases. The
solid phases were differentiated by infrared spectroscopy and X-ray po
wder diffraction. Several of the solid-state phase transformations wer
e mediated by atmospheric moisture. These transformations were studied
as a function of relative humidity with dynamic moisture sorption gra
vimetry (DMSG). DMSG also provided useful measurements of hygroscopici
ty.