The characterisation of selected antidepressant drugs using electrospray ionisation with ion trap mass spectrometry and with quadrupole time-of-flight mass spectrometry and their determination by high-performance liquid chromatography/electrospray ionisation tandem mass spectrometry

Franklin Smyth, Julian Leslie, Stephen McClean, Bernie Hannigan, Hugh McKenna, B Doherty, C Joyce, E O'Kane

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Abstract

The electrospray ionisation ion trap tandem mass spectrometry (ESI-MSn) of selected antidepressant drugs, i.e., citalopram, fluoxetine, mirtazapine, paroxetine, sertraline, and venlafaxine, has been investigated. Sequential product ion fragmentation experiments (MSn) have been performed in order to elucidate the degradation pathways for the [M+H](+) ions and their predominant product ions. These MSn experiments show certain characteristic fragmentations in that functional groups are generally cleaved from the ring systems as molecules such as H2O, amines and phenols. When an aromatic entity is present in a drug molecule together with a nitrogen-containing saturated ring structure as with mirtazapine, fragmentation initially occurs at the latter ring with the former being predictably resistant to fragmentation. Also, when an amine-containing drug molecule such as fluoxetine also contains a functional group, which liberates a phenol with a significantly lower Delta H-f(0) value than that of the corresponding amine, the phenol is preferentially liberated. The structures of product ions proposed for ESI-MSn can be supported by electrospray ionisation quadrupole-time-of-flight tandem mass spectrometry (ESI-QToF-MS/MS). These molecules can be identified and determined in mixtures at low ng/mL concentrations by the application of high-performance liquid chromatography/electrospray ionisation tandem mass spectrometry (HPLC/ESI-MS2), which can also be used for their analysis in hair samples. Copyright (c) 2006 John Wiley & Sons, Ltd.
LanguageEnglish
Pages1637-1642
JournalRapid Communications in Mass Spectrometry
Volume20
Issue number11
DOIs
Publication statusPublished - 2006

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Electrospray ionization
High performance liquid chromatography
Antidepressive Agents
Mass spectrometry
Ions
Amines
Molecules
Fluoxetine
Phenol
Functional groups
Sertraline
Paroxetine
Citalopram
Phenols
Pharmaceutical Preparations
Nitrogen
Experiments
Degradation

Cite this

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title = "The characterisation of selected antidepressant drugs using electrospray ionisation with ion trap mass spectrometry and with quadrupole time-of-flight mass spectrometry and their determination by high-performance liquid chromatography/electrospray ionisation tandem mass spectrometry",
abstract = "The electrospray ionisation ion trap tandem mass spectrometry (ESI-MSn) of selected antidepressant drugs, i.e., citalopram, fluoxetine, mirtazapine, paroxetine, sertraline, and venlafaxine, has been investigated. Sequential product ion fragmentation experiments (MSn) have been performed in order to elucidate the degradation pathways for the [M+H](+) ions and their predominant product ions. These MSn experiments show certain characteristic fragmentations in that functional groups are generally cleaved from the ring systems as molecules such as H2O, amines and phenols. When an aromatic entity is present in a drug molecule together with a nitrogen-containing saturated ring structure as with mirtazapine, fragmentation initially occurs at the latter ring with the former being predictably resistant to fragmentation. Also, when an amine-containing drug molecule such as fluoxetine also contains a functional group, which liberates a phenol with a significantly lower Delta H-f(0) value than that of the corresponding amine, the phenol is preferentially liberated. The structures of product ions proposed for ESI-MSn can be supported by electrospray ionisation quadrupole-time-of-flight tandem mass spectrometry (ESI-QToF-MS/MS). These molecules can be identified and determined in mixtures at low ng/mL concentrations by the application of high-performance liquid chromatography/electrospray ionisation tandem mass spectrometry (HPLC/ESI-MS2), which can also be used for their analysis in hair samples. Copyright (c) 2006 John Wiley & Sons, Ltd.",
author = "Franklin Smyth and Julian Leslie and Stephen McClean and Bernie Hannigan and Hugh McKenna and B Doherty and C Joyce and E O'Kane",
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T1 - The characterisation of selected antidepressant drugs using electrospray ionisation with ion trap mass spectrometry and with quadrupole time-of-flight mass spectrometry and their determination by high-performance liquid chromatography/electrospray ionisation tandem mass spectrometry

AU - Smyth, Franklin

AU - Leslie, Julian

AU - McClean, Stephen

AU - Hannigan, Bernie

AU - McKenna, Hugh

AU - Doherty, B

AU - Joyce, C

AU - O'Kane, E

PY - 2006

Y1 - 2006

N2 - The electrospray ionisation ion trap tandem mass spectrometry (ESI-MSn) of selected antidepressant drugs, i.e., citalopram, fluoxetine, mirtazapine, paroxetine, sertraline, and venlafaxine, has been investigated. Sequential product ion fragmentation experiments (MSn) have been performed in order to elucidate the degradation pathways for the [M+H](+) ions and their predominant product ions. These MSn experiments show certain characteristic fragmentations in that functional groups are generally cleaved from the ring systems as molecules such as H2O, amines and phenols. When an aromatic entity is present in a drug molecule together with a nitrogen-containing saturated ring structure as with mirtazapine, fragmentation initially occurs at the latter ring with the former being predictably resistant to fragmentation. Also, when an amine-containing drug molecule such as fluoxetine also contains a functional group, which liberates a phenol with a significantly lower Delta H-f(0) value than that of the corresponding amine, the phenol is preferentially liberated. The structures of product ions proposed for ESI-MSn can be supported by electrospray ionisation quadrupole-time-of-flight tandem mass spectrometry (ESI-QToF-MS/MS). These molecules can be identified and determined in mixtures at low ng/mL concentrations by the application of high-performance liquid chromatography/electrospray ionisation tandem mass spectrometry (HPLC/ESI-MS2), which can also be used for their analysis in hair samples. Copyright (c) 2006 John Wiley & Sons, Ltd.

AB - The electrospray ionisation ion trap tandem mass spectrometry (ESI-MSn) of selected antidepressant drugs, i.e., citalopram, fluoxetine, mirtazapine, paroxetine, sertraline, and venlafaxine, has been investigated. Sequential product ion fragmentation experiments (MSn) have been performed in order to elucidate the degradation pathways for the [M+H](+) ions and their predominant product ions. These MSn experiments show certain characteristic fragmentations in that functional groups are generally cleaved from the ring systems as molecules such as H2O, amines and phenols. When an aromatic entity is present in a drug molecule together with a nitrogen-containing saturated ring structure as with mirtazapine, fragmentation initially occurs at the latter ring with the former being predictably resistant to fragmentation. Also, when an amine-containing drug molecule such as fluoxetine also contains a functional group, which liberates a phenol with a significantly lower Delta H-f(0) value than that of the corresponding amine, the phenol is preferentially liberated. The structures of product ions proposed for ESI-MSn can be supported by electrospray ionisation quadrupole-time-of-flight tandem mass spectrometry (ESI-QToF-MS/MS). These molecules can be identified and determined in mixtures at low ng/mL concentrations by the application of high-performance liquid chromatography/electrospray ionisation tandem mass spectrometry (HPLC/ESI-MS2), which can also be used for their analysis in hair samples. Copyright (c) 2006 John Wiley & Sons, Ltd.

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