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Acidity of Several Polyprotic Acids, Amiodarone and Quetiapine Hemifumarate in Pure Methanol

Gemma Garrido, Vasco de Nogales, Clara Ràfols, Elisabeth Bosch

Talanta. 2007 Aug 15;73(1):115-20.

PMID: 19071857

Abstract:

Methanol is the organic solvent closest to water and able to dissolve a huge amount of organic compounds. Therefore, it is a good candidate for pK(a) determination of drugs sparingly soluble in water or a basic drug presented as a salt which pK(a) is close to that of its counter-acid. In this work, the acidic dissociation constants in pure methanol of the most common acids used in pharmaceutical preparations (lactic, tartaric, fumaric, maleic and citric) were determined. In addition, the pK(a) values of the antipsychotic quetiapine presented as hemifumarate (Seroquel) and the very insoluble antiarrhythmic amiodarone were also determined by potentiometry. From these values, the aqueous pK(a) of these drugs were estimated by means of previously established equations. Estimated values are consistent with those from literature and show the interest of methanol for drug discovery pK(a) measurements.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP111974722-C Quetiapine hemifumarate salt Quetiapine hemifumarate salt 111974-72-2 Price
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