title: Mechanochemistry of ibuprofen pharmaceutical.
abstract: In this paper mechanochemistry has been studied in view of possible application to detoxification of expired pharmaceuticals. The experiments have been carried out with a commercial medication containing ibuprofen ((RS)-2-(4-(2-methylpropyl)phenyl)propanoic acid) which has been submitted to prolonged milling up to 40h. When Al(OH)(3) is used as co-reagent, the first degradation step induced by the mechanochemical treatment is an acid-base reaction with the ibuprofen carboxylic acid group. The subsequent degradation follows a complex pathway leading to 1-(4-isobutylphenyl)ethanone, 1-isobutyl-4-vinylbenzene and 2-(4-(3-methylbutan-2-yl)phenyl)propan-1-ol after 10h milling and, in addition, 1-(4-acetylphenyl)-2-methylpropan-1-one, 1-(4-(1-hydroxy-2-methylpropyl)phenyl)ethanone and 1-(4-(2-hydroxy-2-methylpropyl)phenyl)ethanone after 40h milling. The degradation reaction path and products have been identified by means of FT-IR spectroscopy, thin layer chromatography, NMR spectroscopy, mass spectroscopy and elemental analysis. The observed ibuprofen decarboxylation makes the drug simultaneously lose both its pharmaceutical activity and toxicity.
authors.affiliation: Università di Napoli Federico II, Dipartimento di Scienze Chimiche, Naples, Italy.
authors.forename: Salvatore
authors.initials: S
authors.lastname: Andini
authors.forename: Adele
authors.initials: A
authors.lastname: Bolognese
authors.forename: Domenico
authors.initials: D
authors.lastname: Formisano
authors.forename: Michele
authors.initials: M
authors.lastname: Manfra
authors.forename: Fabio
authors.initials: F
authors.lastname: Montagnaro
authors.forename: Luciano
authors.initials: L
authors.lastname: Santoro
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D002264:Carboxylic Acids / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D007052:Ibuprofen / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D055595:Mechanical Phenomena; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D002264:Carboxylic Acids; D007052:Ibuprofen