Mass spectral studies of alkaloids related to morphine

Wheeler, Desmond M. S.; Kinstle, Thomas H.; Rinehart, Kenneth L.

doi:10.1021/ja00993a044

Cited by 70 publications

(28 citation statements)

References 4 publications

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“…This was confirmed by the [M-CF 3 COOH] + (m/ z = 282) base ion. The spectrum of 31 also showed characteristic codeine skeleton fragmentation peaks at m/z 229 and 188 supporting the assignment of 31 as trifluoroacetylcodeine [45,46]. …”

Section: Resultssupporting

confidence: 54%

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A ‘cold synthesis’ of heroin and implications in heroin signature analysis

Odell

Skopec²,

McCluskey

2006

Forensic Science International

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Section: Resultssupporting

confidence: 54%

“…The spectrum of 30 also showed significant peaks at m/z 215 and 174, which are characteristic of morphine skeleton fragmentation [45,46]. Similarly, 31 was determined to have [M] + of 395, which is consistent with the addition of a trifluoroacetyl group to codeine.…”

Section: Resultsmentioning

confidence: 89%

A ‘cold synthesis’ of heroin and implications in heroin signature analysis

Odell

Skopec²,

McCluskey

2006

Forensic Science International

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“…The electron impact (EI) mass spectra of morphine and related morphinans are well described (Audier et al, 1965;Hesse and Bernhard, 1975;Wheeler et al, 1967). During the past few years soft ionization methods were intensively used for investigation of morphine and its metabolites (Baumann et al, 2000;Schanzle et al, 1999;Slawson et al, 1999;Weinmann and Svoboda, 1998).…”

Section: Elucidation Of Fragment Ionsmentioning

confidence: 99%

Evaluation of the mass spectrometric fragmentation of codeine and morphine after 13C-isotope biosynthetic labeling

Poeaknapo¹,

Fisinger²,

Zenk³

et al. 2004

Phytochemistry

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“…However, none of these studies compared data of ion trap and triple quad systems. Most of the morphinan type substances have been investigated before by electron impact ionization MS [15][16][17]. Tandem MS instrumentation and the principles of operation have been extensively discussed in the literature [18].…”

mentioning

confidence: 99%

Electrospray tandem mass spectrometric investigations of morphinans

Raith

Neubert

Poeaknapo

et al. 2003

J. Am. Soc. Mass Spectrom.

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In this study positive ESI tandem mass spectra of the [M ϩ H] ϩ ions of morphinan alkaloids obtained using an ion trap MS were compared with those from a triple quadrupole MS. This allows to assess the differences of the tandem-in-time versus the tandem-in-space principle, often hampering the development of ESI MS/MS libraries. Fragmentation pathways and possible fragment ion structures were discussed. In order to obtain elemental composition, accurate mass measurements were performed. According to the MS/MS fragmentation pathway, the investigated compounds can be grouped into 4 subsets: (1) morphine and codeine, (2) morphinone, codeinone, and neopinone, (3) thebaine and oripavine, (4) -7] or CE/ESI-MS [8,9], mostly from a forensic point of view. Frequently fragmentation by CID is described and applied as LC/MS/MS. Two reviews highlight the field [10,11]. Some systematic approaches to the setup of libraries have been undertaken, including data for morphine and codeine [12][13][14]. However, none of these studies compared data of ion trap and triple quad systems. Most of the morphinan type substances have been investigated before by electron impact ionization MS [15][16][17]. Tandem MS instrumentation and the principles of operation have been extensively discussed in the literature [18]. In contrast to magnetic sector instruments, triple quadrupole, quadrupole ion trap, and quadrupole time-of-flight are all considered to perform low collision energy fragmentation. Nevertheless, the obtained tandem mass spectra can look remarkably different. Although the structure elucidation potential of CID was early recognized [19], the setup of ESI-MS/MS libraries was hampered by lacking reproducibility. This article provides comparable ion trap and triple quadrupole MS/MS data of all discussed substances. Accurate mass data of selected morphinans were obtained by quadrupole time-of-flight and FT-ICR mass spectrometry, respectively.

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Mass spectral studies of alkaloids related to morphine

Cited by 70 publications

References 4 publications

A ‘cold synthesis’ of heroin and implications in heroin signature analysis

A ‘cold synthesis’ of heroin and implications in heroin signature analysis

Evaluation of the mass spectrometric fragmentation of codeine and morphine after 13C-isotope biosynthetic labeling

Electrospray tandem mass spectrometric investigations of morphinans

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