Premium
Behavior of amoxicillin in wastewater and river water: identification of its main transformation products by liquid chromatography/electrospray quadrupole time‐of‐flight mass spectrometry
Author(s) -
PérezParada Andrés,
Agüera Ana,
GómezRamos María del Mar,
GarcíaReyes Juan F.,
Heinzen Horacio,
FernándezAlba Amadeo R.
Publication year - 2011
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.4902
Subject(s) - chemistry , electrospray , mass spectrometry , chromatography , wastewater , liquid chromatography–mass spectrometry , environmental engineering , engineering
The identification of transformation products (TPs) of pharmaceuticals in the environment is essentially a challenging task due to the lack of standards and the instrumental capabilities required to detect compounds (sometimes unknowns) that are produced under environmental conditions. In this work, we report the use of liquid chromatography/electrospray quadrupole time‐of‐flight mass spectrometry (LC/QTOF‐MS/MS) as a tool for the identification of amoxicillin (AMX) and its main TPs in wastewater and river water samples. Laboratory degradation experiments of AMX were performed in both alkaline and acidic media in order to confirm that the expected transformation pathway in the aquatic media is through the β‐lactam ring cleavage. A thorough study was carried out with both standards and real samples (wastewater and river water samples). Four compounds were identified as main TPs: both amoxicillin diketopiperacine‐2',5' and amoxilloic acid diastereomers. Amoxilloic acid stereoisomers are reported for the first time in environmental matrices. The transformation product ( 5R )‐amoxicillin diketopiperacine‐2',5' was frequently detected in river waters. Besides, another AMX transformation product formed during analysis was also structurally elucidated for the first time (amoxicilloic acid methyl ester) via accurate mass measurements. Collected data show that although AMX is not present as such in environmental samples, different TPs occur. This study represent a valuable indicator of the potential of LC/QTOF‐MS/MS for the identification and structural elucidation of TPs in the environment using accurate MS/MS experiments, enabling thus the recognition of the environmental transformation pathway. Copyright © 2011 John Wiley & Sons, Ltd.