Mass spectrometry ofN-nitrosamines

Rainey, W.T.; Christie, W. H.; Lijinsky, William

doi:10.1002/bms.1200050606

Cited by 46 publications

(12 citation statements)

References 10 publications

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“…It must be noted that the diagnostic radical cation [M + H − NO] +· ( m/z 239) was observed in the MS 2 spectrum (Figure 3B); however, the intensity of the [M + H − NO] +· peak was very low compared with the [M + H − H 2 O] + peak. The [M + H − H 2 O] + peak likely occurs via a hydrogen‐rearrangement process similar to what is reported for the loss of HO˙ from strained cyclic nitrosamines such as N ‐nitrosoazacyclohexane 21 and alicyclic nitrosamines 25 . However, it is not immediately apparent why this hydrogen‐transfer process would occur readily for NA 3 but was not observed to occur in the piperazine analog (NA 5 ).…”

Section: Resultssupporting

confidence: 62%

“…A proposed fragmentation mechanism for the loss of H 2 O (18 Da) from protonated NA 3 is shown in Scheme 2B. While the loss of 17 Da (HO˙) from protonated nitrosamine model compounds upon MS/MS has been reported in the literature, 21,23–25 to the authors' knowledge this is the first report of a significant loss of 18 Da (H 2 O) from a nitrosamine compound upon MS/MS. It must be noted that the diagnostic radical cation [M + H − NO] +· ( m/z 239) was observed in the MS 2 spectrum (Figure 3B); however, the intensity of the [M + H − NO] +· peak was very low compared with the [M + H − H 2 O] + peak.…”

Section: Resultsmentioning

confidence: 84%

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Mass spectrometry based fragmentation patterns of nitrosamine compounds

Asare

Hoskins

Blessing

et al. 2022

Rapid Comm Mass Spectrometry

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Rationale Nitrosamines are a class of mutagenic substances that can display high carcinogenic potential. New chemical entities may have the potential to form unique nitrosamines specific to the drug substance. It is therefore essential to understand the gas‐phase fragmentation behavior of nitrosamine compounds to enable the development of analytical methods to characterize novel nitrosamine compounds. Methods The gas‐phase fragmentation behavior of eight model nitrosamine compounds representing the common substructures seen in many small molecule pharmaceutical compounds was studied with positive electrospray ionization tandem mass spectrometry (ESI‐MS/MS). The fragmentation patterns of these compounds under various collision parameters available in commercially available mass spectrometers were studied. Results Protonated nitrosamine compounds produced diagnostic fragment ions upon MS/MS. Three primary structure‐dependent fragmentation pathways were observed. The first pathway involves the loss of 30 Da which corresponds to the loss of the NO radical from the protonated nitrosamine compound (Group 1). The second and third fragmentation pathways, which have not been reported for nitrosamine compounds, proceed via the loss of H2O from the protonated nitrosamine compound (Group 2), and elimination and a loss of 46 Da (loss of NH2NO) from the nitrosamine compound (Group 3). Conclusions Results presented in this work provide an overview of the gas‐phase fragmentation patterns of nitrosamine compounds and may be useful in identifying novel nitrosamine compounds in complex matrices.

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Section: Resultssupporting

confidence: 62%

Section: Resultsmentioning

confidence: 84%

Mass spectrometry based fragmentation patterns of nitrosamine compounds

Asare

Hoskins

Blessing

et al. 2022

Rapid Comm Mass Spectrometry

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“…A comparison of the performance of several detectors was reported by Fine et al (1976c). Descriptions of the mass spectrometric properties of N ‐nitrosamines and some analytical applications have been described by Libbey and Scanlan (1985), Rainey et al (1978), Webb et al (1983).…”

Section: Methodsmentioning

confidence: 99%

The determination of N-nitrosamines in food

Crews

2010

Quality Assurance and Safety of Crops &Amp; Foods

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Introduction N‐nitrosamines are formed in food as a result of natural chemical interactions, but mainly through food processing activity. Most are potent carcinogens and their determination is therefore of considerable importance. They exist in various chemical forms and have been measured by colorimetric and spectroscopic methods following gas or liquid chromatography or as a total N‐nitroso group by measurement of chemically released nitric oxide. Objectives To provide an overview of the available methods for the analysis of N‐nitrosamines in food that includes recently developments. Methods The literature was reviewed from the discovery of the N‐nitrosamine problem and the introduction on the N‐nitroso‐specific detector. Results The evaluation shows that analytical detection methods for volatile N‐nitrosamines in food have changed little since the introduction on the N‐nitroso‐specific detector and that research into the occurrence and formation of both non‐volatile N‐nitrosamines and the apparent total N‐nitroso content (ATNC) have declined. Methods for measuring the apparent total N‐nitroso content have not been improved significantly in recent years. Conclusion Modern sample extraction techniques and mass spectrometric methods for the volatile N‐nitrosamines have been applied more extensively to water analysis and offer a good opportunity to improve the determination of these carcinogens in food and make the analysis more widely available. Developments in liquid chromatography‐mass spectrometry should provide an avenue for renewed interest in non‐volatile N‐nitrosamines, and could help with the identification of novel compounds whose presence is suggested by the high apparent total N‐nitroso content of some foods.

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“…Extraction of the nitrosamine with a suitable solvent such as chloroform, followed by separation via gas chromatographic (GC) methods in conjunction with mass spectrometric (MS) identification, led to the important establishment of general behavior patterns of nitrosamines in the mass spectrometer [9]. High performance liquid chromatography (HPLC) has become the dominant method for resolving mixtures of volatile and nonvolatile nitrosamines, as well as for the separation of nitrosamine rotamers [ 101. This method also requires coupling to MS however, for the confirmation of individual Nnitroso compounds [I 11.…”

Section: Introductionmentioning

confidence: 99%

The electrochemical determination of N‐nitrosamines at polymer modified electrodes via an adsorptive stripping voltammetric regime

1997

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An adsorptive linear sweep stripping voltammetric method has been developed for the determination of nitrosamines at polymer modified gold electrodes. N-nitroso-N-butyl-N-propylamine has been quantified over a lo-'' M to M concentration range at Nafion modified electrodes. CA coatings inhibited the determination of N-nitroso-N-butyl-N-propylamine, while small enhancements were observed at CAB modified electrodes. This improvement may be due to the anionic butyrate groups within the CAB polymer facilitating nitrosamine sorption. It is postulated, that the insulating effect of the polymer and the incorporation of anionic moieties compete to give either a net enhancement or depreciation of analytical sensitivity .

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Mass spectrometry ofN-nitrosamines

Cited by 46 publications

References 10 publications

Mass spectrometry based fragmentation patterns of nitrosamine compounds

Mass spectrometry based fragmentation patterns of nitrosamine compounds

The determination of N-nitrosamines in food

The electrochemical determination of N‐nitrosamines at polymer modified electrodes via an adsorptive stripping voltammetric regime

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