Isomerization of cannabidiol and Δ9-tetrahydrocannabinol during positive electrospray ionization. In-source hydrogen/deuterium exchange experiments by flow injection hybrid quadrupole-time-of-flight mass spectrometry

Rapid Communications in Mass Spectrometry

Volumn 26, Issue 12, 2012, Pages 1407-1414

  Broecker, Sebastian ^a   Pragst, Fritz ^a  

^a CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; DRUG PRODUCTS; HYDROGEN; ISOMERS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

COLLISION-INDUCED DISSOCIATION SPECTRA; FLOW INJECTION; HYDROGEN ATOMS; HYDROGEN/DEUTERIUM EXCHANGE; ISOMERISATION; LIQUID CHROMATOGRAPHY/TANDEM MASS SPECTROMETRY; NEGATIVE ELECTROSPRAY IONIZATIONS; OH-GROUPS; POSITIVE ELECTROSPRAY IONIZATION; QUADRUPOLE TIME OF FLIGHT MASS SPECTROMETRY;

ELECTROSPRAY IONIZATION;

EID: 84861315673     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.6244     Document Type: Article

References (17)

1. S.B. Grauwiler, A. Scholer, J. Drewe,. Development of a LC/MS/MS method for the analysis of cannabinoids in human EDTA-plasma and urine after small doses of cannabis sativa extracts. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2007, 850, 515.
2. E. Jagerdeo, J.E. Schaff, M.A. Montgomery, M.A. LeBeau,. A semi-automated solid-phase extraction liquid chromatography/tandem mass spectrometry method for the analysis of tetrahydrocannabinol and metabolites in whole blood. Rapid Commun. Mass Spectrom. 2009, 23, 2697.
3. A. Gronewold, G. Skopp,. A preliminary investigation on the distribution of cannabinoids in man. Forensic Sci. Int. 2011, 210, e7.
4. D.M. Schwope, K.B. Scheidweiler, M.A. Huestis,. Direct quantification of cannabinoids and cannabinoid glucuronides in whole blood by liquid chromatography-tandem mass spectrometry. Anal. Bioanal. Chem. 2011, 401, 1273.
5. S. Broecker, S. Herre, B. Wüst, J. Zweigenbaum, F. Pragst,. Development and practical application of a library of CID accurate mass spectra of more than 2,500 toxic compounds for systematic toxicological analysis by LC-QTOF-MS with data-dependent acquisition. Anal. Bioanal. Chem. 2011, 400, 101.
6. R. Adams, D.C. Pease, C.K. Cain, B.R. Baker, J.H. Clark, H. Wolff, R.B. Wearn,. Conversion of cannabidiol to a product with marihuana activity. A type reaction for synthesis of analogous substances. Conversion of cannabidiol to cannabinol. J. Am. Chem. Soc. 1940, 62, 2245.
7. Y. Gaoni, R. Mechoulam,. Hashish-VII. The isomerization of cannabidiol to tetrahydrocannabinols. Tetrahedron 1966, 22, 1481.
8. Y. Gaoni, R. Mechoulam,. Concerning the isomerization of D1- to D6-tetrahydrocannabinol. J. Am. Chem. Soc. 1966, 88, 5673.
9. R. Mechoulam, L. Hanus,. Cannabidiol: an overview of some chemical and pharmacological aspects. Part I: chemical aspects. Chem. Phys. Lipids 2002, 121, 35.
10. Z. Takáts, G. Schlosser, K. Vékey,. Hydrogen/deuterium exchange of electrosprayed ions in the atmospheric interface of a commercial triple-quadrupole mass spectrometer. Int. J. Mass Spectrom. 2003, 228, 729.
11. J.C. Wolff, A.M. Laures,. 'On-the-fly' hydrogen/deuterium exchange liquid chromatography/mass spectrometry using a dual-sprayer atmospheric pressure ionisation source. Rapid Commun. Mass Spectrom. 2006, 20, 3769.
12. W. Lam, R. Ramanathan,. In electrospray ionization source hydrogen/deuterium exchange LC-MS and LC-MS/MS for characterization of metabolites. J. Am. Soc. Mass Spectrom. 2002, 13, 345.
13. A. Tolonen, M. Turpeinen, J. Uusitalo, O. Pelkonen,. A simple method for differentiation of monoisotopic drug metabolites with hydrogen-deuterium exchange liquid chromatography/electrospray mass spectrometry. Eur. J. Pharm. Sci. 2005, 25, 155.
14. S.T. Esswein, H.V. Florance, L. Baillie, J. Lippens, P.E. Barran,. A comparison of mass spectrometry based hydrogen deuterium exchange methods for probing the cyclophilin A cyclosporin complex. J. Chromatogr. A 2010, 1217, 6709.
15. M. Lacroix, J.C. Garrigues, F. Couderc,. Reaction of naphthalene-2,3- dicarboxaldehyde with enkephalins for LC-fluorescence and LC-MS analysis: conformational studies by molecular modeling and H/D-exchange mass spectrometry. J. Am. Soc. Mass Spectrom. 2007, 18, 1706.
16. M.D. Sierra, A. Furey, B. Hamilton, M. Lehane, K.J. James,. Elucidation of the fragmentation pathways of azaspiracids, using electrospray ionisation, hydrogen/deuterium exchange, and multiple-stage mass spectrometry. J. Mass Spectrom. 2003, 38, 1178.
17. N.B. Cech, C.G. Enke,. Practical implications of some recent studies in electrospray ionization fundamentals. Mass Spectrom. Rev. 2001, 20, 362.