Sites of protonation in phenothiazines: Methane and ammonia chemical ionization mass spectra

Flurer, Rick A.; Busch, Kenneth L.

doi:10.1002/oms.1210230210

Cited by 9 publications

(4 citation statements)

References 14 publications

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“…Flurer and Busch had compared, for 10 phenothiazine derivatives, the positive-ion methane and ammonia spectra with secondary ion mass spectra (SIMS). [14] The same fragmentations were observed for both ionization methods, but relative abundances were higher in SIMS spectra.…”

Section: Introductionsupporting

confidence: 54%

“…The elimination of sulur atom was previously reported for ESI-MS n of chlorpromazine. [15,16] It was also widely described for EI [7 -11] and CI analyses [14] of various phenothiazine compounds. However, in the case of MPZ and AMPZ, no H loss was observed, in contrast to other phenothiazine compounds which were analyzed by CI ionization.…”

Section: Resultsmentioning

confidence: 99%

“…However, in the case of MPZ and AMPZ, no H loss was observed, in contrast to other phenothiazine compounds which were analyzed by CI ionization. [14] The loss of 79 m/z unit was recurrent and corresponded to the elimination of the radical SO 2 CH 3 . Radical cations were thus obtained from the transitions: A (m/z 429) to F (m/z 350) (Fig.…”

Section: Resultsmentioning

confidence: 99%

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Fragmentation pathways of metopimazine and its metabolite using ESI‐MSⁿ, HR‐MS and H/D exchange

et al. 2010

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Metopimazine (MPZ) is a phenothiazine derivative used to prevent emesis during chemotherapy where few structural analysis of the aforementioned compound have been described in the literature. Thus, this work reports, for the first time, the detailed study of fragmentation pathways of MPZ and its metabolite (AMPZ) using electrospray ionization (EI) with multistage mass spectrometry (ESI-MS n ) in positive-ion mode. The structures of 21 product ions were identified and their accurate masses were determined using high resolution mass spectrometry (HRMS) experiments. Characteristic product ions of these two phenothiazine derivatives are more particularly displayed along with differences between their relative abundances and their structures checked by H/D exchange experiments.

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Section: Introductionsupporting

confidence: 54%

Section: Resultsmentioning

confidence: 99%

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Fragmentation pathways of metopimazine and its metabolite using ESI‐MSⁿ, HR‐MS and H/D exchange

et al. 2010

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“…Another of these studies used metastable ions, exact mass measurements, and deuterated derivatives to investigate the fragmentation pathways of phenothiazines [9]. The sites of protonation in phenothiazines have been determined using methane and ammonia CI mass spectra with high resolution mass measurements to confirm the empirical formulas of fragment ions [10].…”

Section: Comparison Ofmaps Rules To Documented Fragmentation Pathwaysmentioning

confidence: 99%

Evaluation of automatically generated substructure identification rules from tandem mass spectra

Hart

Wade

Nourse

et al. 1992

J. Am. Soc. Mass Spectrom.

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Substructure identification rules for phenothiazine and barbiturate substructures were generated by using a new version of the Method for Analyzing Patterns in Spectra (MAPS) software. This software uses tandem mass spectra and known substructure content of reference compounds to provide "feature-combination" rules. A feature-combination is a series of tandem mass spectral features which are completely unique to compounds containing a specified substructure. The current reference databases contain over 11,000 daughter spectra of 100 compounds acquired at two different collision gas pressures (i.e., single- and multiple-collision conditions). The results of rule evaluation procedures are presented and include a comparison of the spectral features developed in rule generation to those identified in documented fragmentation pathways of the indicated substructure. Two potential sources of error due to spectral feature and substructure "cross-correlation" were identified. If errors occur, they can be detected by calculating cross-correlation coefficients and edited from the rules. A beneficial cross-correlation involving feature-combinations was also discovered. The rules obtained by using single- and multiple-collision data were further evaluated by applying them to tandem mass spectra of 20 test compounds (compounds not in the reference database). The results of these evaluations give a good indication of the utility of the rules for use in an automated structure elucidation system for tandem mass spectrometry data.

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Comparative chemical ionization mass spectra of tricyclic antidepressant amines and related compounds

Schildcrout¹,

Geidner²

1989

Org. Mass Spectrom.

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Positiveion methane chemical ionization (CI) mass spectra were obtained for seven underivatized tricyclic amines: amitriptyline, nortriptyline, protriptyline, imipramine, desipramine, cyclobenzaprine and cyproheptadine. Some discrepancies in previously reported spectra were noted. Spectra of protriptyline, cyclobenzaprine and cyproheptadine are reported for the first time. Comparisons are made among the CI spectra and with electron ionization spectra, and relative abundances of major CI ions among the seven compounds are rationalized in terms of substituent and geometric effects.In most cases low-mass iminium ions from anion abstraction were more abundant than IMH]'. Hydride abstraction and adduct formation with reagent-gas ions were important. The three heterocyclic amines gave abundant W ) ' ' by electron transfer. Protonation at the nitrogen atom on the side chain followed by amine elimination gave tricyclic aromatic fragment ions.

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Sites of protonation in phenothiazines: Methane and ammonia chemical ionization mass spectra

Cited by 9 publications

References 14 publications

Fragmentation pathways of metopimazine and its metabolite using ESI‐MSⁿ, HR‐MS and H/D exchange

Fragmentation pathways of metopimazine and its metabolite using ESI‐MSⁿ, HR‐MS and H/D exchange

Evaluation of automatically generated substructure identification rules from tandem mass spectra

Comparative chemical ionization mass spectra of tricyclic antidepressant amines and related compounds

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Sites of protonation in phenothiazines: Methane and ammonia chemical ionization mass spectra

Cited by 9 publications

References 14 publications

Fragmentation pathways of metopimazine and its metabolite using ESI‐MSn, HR‐MS and H/D exchange

Fragmentation pathways of metopimazine and its metabolite using ESI‐MSn, HR‐MS and H/D exchange

Evaluation of automatically generated substructure identification rules from tandem mass spectra

Comparative chemical ionization mass spectra of tricyclic antidepressant amines and related compounds

Contact Info

Product

Resources

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Fragmentation pathways of metopimazine and its metabolite using ESI‐MSⁿ, HR‐MS and H/D exchange

Fragmentation pathways of metopimazine and its metabolite using ESI‐MSⁿ, HR‐MS and H/D exchange