The polar molecule, fluorouracil, is a monoanion at pH 10 and may be quantitatively extracted from aqueous solutions with quaternary alkylammonium ions into an organic solvent such as dichloromethane as the ion-pair. Extraction constants of fluorouracil with the tetrapentylammonium ion in dichloromethane or dichloromethane-1-butanol (9:1) and with the tetrahexylammonium ion in dichloromethane were determined. Slope analysis demonstrated that association of the ion components in the aqueous phase occurred as the side reaction. A column ion-pair extraction technique, using tetrapentylammonium as the counterion and dichloromethane as the eluting phase, was developed and allowed quantitative transfer of fluorouracil to the organ solvent. The applicability of this method was shown by determining plasma levels of fluorouracil in cancer patients to whom 1 g of active substance was administered intravenously.
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