Mechanochemistry of ibuprofen pharmaceutical

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• 作者：Salvatore Andini^a ; Adele Bolognese^a ; Domenico Formisano^a ; Michele Manfra^b ; Fabio Montagnaro^a ; Luciano Santoro^a ; ^{santoro@unina.it}
• 关键词：Mechanochemistry ; Ibuprofen ; Expired pharmaceuticals ; Detoxification ; Decarboxilation
• 刊名：Chemosphere
• 出版年：2012
• 期刊代码：15_00456535
• 类别：env
• 出版时间：July, 2012
• 卷：88
• 期：5
• 页码：548-553
• 文件大小：797 K

摘要

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 40 h. 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 10 h 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 40 h 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.