title: Nucleophilic aminoalcohol-catalyzed degradation of indomethacin in aqueous solution.
abstract: The catalytic effect of ethanolamine and related aminoalcohols on the rate of degradation of indomethacin in alkaline solutions has been shown to be due to a nucleophilic reaction mechanism involving formation of an intermediate ester consisting of p-chlorobenzoic acid and aminoalcohol through the reaction of aminoalcohol hydroxyl group with carbonyl carbon of indomethacin amide group. This ester subsequently undergoes a rapid intramolecular aminolysis to yield a stable p-chlorobenzamide derivative and/or is hydrolyzed to p-chlorobenzoic acid, depending on the chemical structure of aminoalcohols. No catalytic effect was observed with the amines not containing a hydroxyl group.
authors.forename: H
authors.initials: H
authors.lastname: Tomida
authors.forename: N
authors.initials: N
authors.lastname: Kuwada
authors.forename: Y
authors.initials: Y
authors.lastname: Tsuruta
authors.forename: K
authors.initials: K
authors.lastname: Kohashi
authors.forename: S
authors.initials: S
authors.lastname: Kiryu
mesh_terms: D000605:Amino Alcohols; D055598:Chemical Phenomena; D002621:Chemistry; D007213:Indomethacin / Q000032:analysis*; D007700:Kinetics; D012996:Solutions
chemical_list: D000605:Amino Alcohols; D012996:Solutions; D007213:Indomethacin