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 prolongedmilling 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-vinylbenzeneand 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 identifiedby means of FT-IR spectroscopy, thin layer chromatography,NMRspectroscopy, mass spectroscopy and elemental analysis. The observed ibuprofen decarboxylation makes the drug simultaneously lose both its pharmaceutical activity and toxicity.

Mechanochemistry of ibuprofen pharmaceutical / Andini, Salvatore; Bolognese, Adele; D., Formisano; M., Manfra; Montagnaro, Fabio; Santoro, Luciano. - In: CHEMOSPHERE. - ISSN 0045-6535. - 88:(2012), pp. 548-553. [10.1016/j.chemosphere.2012.03.025]

Mechanochemistry of ibuprofen pharmaceutical

ANDINI, SALVATORE;BOLOGNESE, ADELE;MONTAGNARO, FABIO;SANTORO, LUCIANO
2012

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 prolongedmilling 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-vinylbenzeneand 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 identifiedby means of FT-IR spectroscopy, thin layer chromatography,NMRspectroscopy, mass spectroscopy and elemental analysis. The observed ibuprofen decarboxylation makes the drug simultaneously lose both its pharmaceutical activity and toxicity.
2012
Mechanochemistry of ibuprofen pharmaceutical / Andini, Salvatore; Bolognese, Adele; D., Formisano; M., Manfra; Montagnaro, Fabio; Santoro, Luciano. - In: CHEMOSPHERE. - ISSN 0045-6535. - 88:(2012), pp. 548-553. [10.1016/j.chemosphere.2012.03.025]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/450539
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