Characterisation of selected drugs with nitrogen-containing saturated ring structures by use of electrospray ionisation with ion-trap mass spectrometry

Franklin Smyth, VN Ramachandran, E O'Kane, D Coulter

    Research output: Contribution to journalArticle

    21 Citations (Scopus)

    Abstract

    The electrospray ionisation-ion-trap mass spectrometry (ESI-MSn) of selected drugs with nitrogen-containing saturated ring structures has been investigated. Sequential product-ion fragmentation experiments (MSn) have been performed to elucidate degradation pathways for the [M+H](+) ions and their predominant fragment ions. These MSn experiments result in characteristic fragmentations in which functional groups are generally cleaved from the ring systems as neutral molecules such as H2O, amines, alkenes, esters, carboxylic acids, etc. When such a nitrogen-containing drug molecule also contains a functional group, such as an ester, that on liberation as a neutral molecule has a significantly lower -DeltaH(f)degrees value than that of the corresponding amine then the former is preferentially liberated. Furthermore, when an aromatic entity is present in these drug molecules together with the nitrogen-containing saturated ring structure fragmentation of the latter ring occurs with the former, predictably, being resistant to fragmentation. The structures of fragment ions proposed for ESI-MSn can be supported by electrospray ionisation-quadrupole time-of-flight mass spectrometry (ESI-QTOFMS). The data presented in this paper therefore provide useful information on the structure of these heterocyclic compounds which could be used to characterise unknown drug compounds isolated from natural sources, for example.
    LanguageEnglish
    Pages1305-1312
    JournalAnalytical and Bioanalytical Chemistry
    Volume378
    Issue number5
    DOIs
    Publication statusPublished - Mar 2004

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    Electrospray ionization
    Mass spectrometry
    Nitrogen
    Ions
    Molecules
    Pharmaceutical Preparations
    Functional groups
    Amines
    Esters
    Heterocyclic Compounds
    Alkenes
    Carboxylic Acids
    Experiments
    Degradation

    Cite this

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    title = "Characterisation of selected drugs with nitrogen-containing saturated ring structures by use of electrospray ionisation with ion-trap mass spectrometry",
    abstract = "The electrospray ionisation-ion-trap mass spectrometry (ESI-MSn) of selected drugs with nitrogen-containing saturated ring structures has been investigated. Sequential product-ion fragmentation experiments (MSn) have been performed to elucidate degradation pathways for the [M+H](+) ions and their predominant fragment ions. These MSn experiments result in characteristic fragmentations in which functional groups are generally cleaved from the ring systems as neutral molecules such as H2O, amines, alkenes, esters, carboxylic acids, etc. When such a nitrogen-containing drug molecule also contains a functional group, such as an ester, that on liberation as a neutral molecule has a significantly lower -DeltaH(f)degrees value than that of the corresponding amine then the former is preferentially liberated. Furthermore, when an aromatic entity is present in these drug molecules together with the nitrogen-containing saturated ring structure fragmentation of the latter ring occurs with the former, predictably, being resistant to fragmentation. The structures of fragment ions proposed for ESI-MSn can be supported by electrospray ionisation-quadrupole time-of-flight mass spectrometry (ESI-QTOFMS). The data presented in this paper therefore provide useful information on the structure of these heterocyclic compounds which could be used to characterise unknown drug compounds isolated from natural sources, for example.",
    author = "Franklin Smyth and VN Ramachandran and E O'Kane and D Coulter",
    year = "2004",
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    language = "English",
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    Characterisation of selected drugs with nitrogen-containing saturated ring structures by use of electrospray ionisation with ion-trap mass spectrometry. / Smyth, Franklin; Ramachandran, VN; O'Kane, E; Coulter, D.

    In: Analytical and Bioanalytical Chemistry, Vol. 378, No. 5, 03.2004, p. 1305-1312.

    Research output: Contribution to journalArticle

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    AB - The electrospray ionisation-ion-trap mass spectrometry (ESI-MSn) of selected drugs with nitrogen-containing saturated ring structures has been investigated. Sequential product-ion fragmentation experiments (MSn) have been performed to elucidate degradation pathways for the [M+H](+) ions and their predominant fragment ions. These MSn experiments result in characteristic fragmentations in which functional groups are generally cleaved from the ring systems as neutral molecules such as H2O, amines, alkenes, esters, carboxylic acids, etc. When such a nitrogen-containing drug molecule also contains a functional group, such as an ester, that on liberation as a neutral molecule has a significantly lower -DeltaH(f)degrees value than that of the corresponding amine then the former is preferentially liberated. Furthermore, when an aromatic entity is present in these drug molecules together with the nitrogen-containing saturated ring structure fragmentation of the latter ring occurs with the former, predictably, being resistant to fragmentation. The structures of fragment ions proposed for ESI-MSn can be supported by electrospray ionisation-quadrupole time-of-flight mass spectrometry (ESI-QTOFMS). The data presented in this paper therefore provide useful information on the structure of these heterocyclic compounds which could be used to characterise unknown drug compounds isolated from natural sources, for example.

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