Photochemical behaviour of propranolol in environmental waters: the hydroxylated photoproducts

Anne Piram 1 René Faure 1 Henry Chermette 2 Claire Bordes 2 Bernard Herbreteau 3 Arnaud Salvador 4
1 ISA - Institut des Sciences Analytiques
2 CHEMOD - CHEmometry et MODélisation moléculaire
ISA - Institut des Sciences Analytiques
3 TECHSEP - TECHniques de SEParations
ISA - Institut des Sciences Analytiques
4 ANABIO - ANAlyse BIOmoléculaire RMN et spectrométrie de masse
ISA - Institut des Sciences Analytiques
Abstract : The UV irradiation of propranolol, one of the beta-blockers currently used in cardiac medicine, was studied. During irradiation, the samples were analysed by LC/MS/MS, using a Waters Symmetry C-18 (3.5 mu m 150 x 2.1 mm) column. The main photoproducts were identified from mono-, di- and tri-hydroxylation of the propranolol naphthalenic skeleton. Hydroxyl group positions were predicted by means of theoretical calculations. Partial charge calculations of the propranolol atoms predicted the formation of four mono-hydroxylated compounds, two of them being the most probable. From these two compounds, three di-hydroxylated compounds were predicted. Then the calculations from the two most probable di-hydroxylated compounds were used to propose three tri-hydroxylated propranolol compounds. It was found that the same hydroxylated photoproducts are formed in pure water and in treatment plant waste water.
Keywords : propranolol water treatment plant liquid chromatography mass spectrometry hydroxylated photoproducts RECEPTOR-BLOCKING PHARMACEUTICALS DENSITY-FUNCTIONAL THEORY BETA-BLOCKERS AQUATIC ENVIRONMENT RISK-ASSESSMENT TREATMENT-PLANT PHOTODEGRADATION DEGRADATION PHOTOLYSIS EFFLUENTS
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https://hal.archives-ouvertes.fr/hal-00876038
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Submitted on : Wednesday, October 23, 2013 - 3:19:20 PM
Last modification on : Thursday, February 8, 2018 - 11:10:19 AM

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ISA | ENS-LYON | INC-CNRS | UNIV-LYON1

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Anne Piram, René Faure, Henry Chermette, Claire Bordes, Bernard Herbreteau, et al.. Photochemical behaviour of propranolol in environmental waters: the hydroxylated photoproducts. International Journal of Environmental Analytical Chemistry, Taylor & Francis, 2012, 92 (1), pp.96-109. ⟨10.1080/03067319.2010.497920⟩. ⟨hal-00876038⟩

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