Thermal and X-ray analysis of racemic bupivacaine hydrochloride

Sykula-Zajac, A.; Lodyga-Chruscinska, E.; Palecz, B.; Dinnebier, R. E.; Griesser, U. J.; Niederwanger, V.

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Thermal and X-ray analysis of racemic bupivacaine hydrochloride

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Dinnebier, R. E.
Scientific Facility X-Ray Diffraction (Robert E. Dinnebier), Max Planck Institute for Solid State Research, Max Planck Society;

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Sykula-Zajac, A., Lodyga-Chruscinska, E., Palecz, B., Dinnebier, R. E., Griesser, U. J., & Niederwanger, V. (2011). Thermal and X-ray analysis of racemic bupivacaine hydrochloride. Journal of Thermal Analysis and Calorimetry, 105(3), 1031-1036.

Cite as: https://hdl.handle.net/21.11116/0000-000E-BF5F-2

Abstract

An amide-type local anesthetic drug, bupivacaine hydrochloride (BupiHCl), in the form of racemate is listed in the European and American pharmacopoeias and continues to be used in medicine. Thermal and X-ray analysis of commercial BupiHCl monohydrate was performed by differential scanning calorimetry with thermogravimetry, hot stage microscopy, and X-ray diffraction. Endothermic dehydration occurs at the temperature range of 73-130 A degrees C for DSC-TG 111 (Setaram) and at 83-150 A degrees C for DSC 404 (Netzsch). Both curves at 2 and 10 A degrees C min(-1) clearly reflect phase transformation of anhydrous Form I into II before reaching the melting point. A well-defined exothermic phase transition of BupiHCl was detected at a lower heating rate. Temperature-resolved X-ray diffraction in conjunction with DSC led to determining a similarity between the obtained thermal events. Microscopic investigation also confirmed the above-mentioned transformations.