Monatshefte für Chemie - Chemical Monthly

, Volume 147, Issue 1, pp 53–60 | Cite as

Electrochemical oxidation of zopiclone

  • Jakub Táborský
  • Martin Švidrnoch
  • Ondřej Kurka
  • Lucie Borovcová
  • Petr Bednář
  • Petr Barták
  • Jana Skopalová
Original Paper
  • 187 Downloads

Abstract

Electrochemical behaviour of zopiclone was investigated on glassy carbon electrode in static and rotation disc arrangement. Strong influence of kinetics and adsorption phenomena on the electrode processes was proved by voltammetric techniques. Controlled potential electrolysis in off-line and on-line combination with tandem mass spectrometry was employed for investigation of the products of electrochemical oxidation. N-Desmethyl zopiclone was identified and three other oxidation products formed by an introduction of one or two oxygen atom(s) to the molecule of zopiclone (including zopiclone N-oxide) were characterized. Based on mass spectrometric investigation of those products, piperazine moiety was proved as a target of electrochemical oxidation of zopiclone. Since N-desmethyl zopiclone and zopiclone N-oxide have been reported as products of enzymatic metabolism of the drug, the combination of electrochemistry with mass spectrometry may be considered as a reliable tool for simulation of some metabolic transformations.

Graphical abstract

Keywords

Electrochemistry Mass spectroscopy Voltammetry N-Desmethyl zopiclone 

Notes

Acknowledgments

The authors gratefully acknowledge the financial support by the Ministry of Education, Youth and Sports of the Czech Republic (project LO1305).

Supplementary material

706_2015_1602_MOESM1_ESM.pdf (248 kb)
Supplementary material 1 (PDF 247 kb)

References

  1. 1.
    Beyquemont L, Mouajjah S, Escaffre O, Beaune P, Funkc-Brentano CH, Jaillon P (1999) Drug Metab Dispos 27:1068Google Scholar
  2. 2.
    Tono MA, Jabor VAP, Bonato PS (2013) Anal Bioanal Chem 405:267CrossRefGoogle Scholar
  3. 3.
    Jantos R, Vermeeren A, Sabljic D, Remaekers JG, Skopp G (2013) Int J Legal Med 127:69CrossRefGoogle Scholar
  4. 4.
    Tonon MA, Bonato PS (2012) Electrophoresis 33:1606CrossRefGoogle Scholar
  5. 5.
    Largeron M, Fleury MB (1989) J Pharm Sci 78:627CrossRefGoogle Scholar
  6. 6.
    Fernandez C, Gimenez F, Mayrargue J, Thuillier A, Farinotti R (1995) Chirality 7:297CrossRefGoogle Scholar
  7. 7.
    El-Shaheny RN, Alattas A, Nasr JJ, El-Enany N, Belal F (2012) J Chromatogr B 907:49CrossRefGoogle Scholar
  8. 8.
    Mannaert E, Tytgat J, Daenens P (1997) J Anal Toxicol 21:208CrossRefGoogle Scholar
  9. 9.
    Viré J-C, Zhang H, Quarin G, Patriarche GJ (1993) Talanta 40:313CrossRefGoogle Scholar
  10. 10.
    Yilmaz S (2009) Colloids Surf B 71:79CrossRefGoogle Scholar
  11. 11.
    The British Pharmacopoeia (2009) Her Majesty’s Stationary Office, London (electronic version) Google Scholar
  12. 12.
    Paw B, Misztal G (2000) J Pharm Biomed Anal 23:819CrossRefGoogle Scholar
  13. 13.
    Bouklouze AA, Viré J-C, Quarin GC, Kauffmann J-M (1994) Electroanalysis 6:1045CrossRefGoogle Scholar
  14. 14.
    Van Bocxlaer L, Meyer E, Clauwaert K, Lambert W, Piette M, De Leenheer A (2006) J Anal Toxicol 1:52Google Scholar
  15. 15.
    Tonon MA, Jabor VAP, Bonato PS (2011) Anal Bioanal Chem 400:3517CrossRefGoogle Scholar
  16. 16.
    Fernandez C, Gimenez F, Baune B, Maradeix V, Thuillier A, Farinotti R (1993) J Chromatogr A 617:271CrossRefGoogle Scholar
  17. 17.
    Foster RT, Caillé G, Ngoc AH, Lemko CH, Kherani R, Pasutto FM (1994) J Chromatogr B 658:161CrossRefGoogle Scholar
  18. 18.
    Lohmann W, Baumann A, Karst U (2010) LC-GC Europe 1:7Google Scholar
  19. 19.
    Jahn S, Karst U (2012) J Chromatogr A 1259:16CrossRefGoogle Scholar
  20. 20.
    Jurva U, Wikström HV, Weidolf L, Bruins AP (2003) Rapid Commun Mass Spectrom 17:800CrossRefGoogle Scholar
  21. 21.
    Permentier HP, Bruins AP (2004) J Am Soc Mass Spectrom 15:1707CrossRefGoogle Scholar
  22. 22.
    Chen H, Zhang Y, Mutlib AE, Zhong M (2006) Anal Chem 78:2413CrossRefGoogle Scholar
  23. 23.
  24. 24.
    Smyth WF, Joyce C, Ramachandran VN, O’Kane E, Coulter D (2004) Anal Chim Acta 506:203CrossRefGoogle Scholar
  25. 25.
    Johansson T, Weidolf L, Jurva U (2007) Rapid Commun Mass Spectrom 21:2323CrossRefGoogle Scholar
  26. 26.
    Hrbac J, Halouzka V, Trnkova L, Vacek J (2014) Sensors 14:13943CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Wien 2015

Authors and Affiliations

  • Jakub Táborský
    • 1
  • Martin Švidrnoch
    • 1
  • Ondřej Kurka
    • 1
  • Lucie Borovcová
    • 1
  • Petr Bednář
    • 1
  • Petr Barták
    • 1
  • Jana Skopalová
    • 1
  1. 1.Regional Centre of Advanced Technologies and Materials, Department of Analytical Chemistry, Faculty of SciencePalacký UniversityOlomoucCzech Republic

Personalised recommendations