Sensitive hydrophilic interaction liquid chromatography/tandem mass spectrometry method for rapid detection, quantification and confirmation of cathinone-derived designer drugs for doping control in equine plasma

Rapid Communications in Mass Spectrometry

Volumn 28, Issue 2, 2014, Pages 217-229

  Li, Xiaoqing ^a   Uboh, Cornelius E ^a,b   Soma, Lawrence R ^a   Liu, Ying ^a   Guan, Fuyu ^a   Aurand, Craig R ^c   Bell, David S ^c   You, Youwen ^a   Chen, Jinwen ^a   Maylin, George A ^d  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b WEST CHESTER UNIVERSITY   (United States)

^c Pharmaceutical and Bioanalytical Research   (United States)

^d State University of New York   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COLUMN CHROMATOGRAPHY; CONTROLLED DRUG DELIVERY; DRUG PRODUCTS; HIGH PRESSURE LIQUID CHROMATOGRAPHY; HYDROPHILICITY; MASS SPECTROMETRY; SCREENING;

ANALYTES; BANNED SUBSTANCES; CATHINONE; DESIGNER DRUGS; DOPING CONTROL; HYDROPHILIC INTERACTION LIQUID CHROMATOGRAPHIES; LIQUID CHROMATOGRAPHY-TANDEM MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY/TANDEM MASS SPECTROMETRY; MULTIPLE REACTION MONITORING; RAPID DETECTION;

ELECTROSPRAY IONIZATION;

ALKALOID; CATHINONE; CENTRAL STIMULANT AGENT; DESIGNER DRUG; ETHER DERIVATIVE; TERT BUTYL METHYL ETHER;

ANIMAL; ANIMAL DISEASE; ARTICLE; BLOOD; CHEMICAL PHENOMENA; CHEMISTRY; DOPING; EVALUATION STUDY; HORSE; LIMIT OF DETECTION; LIQUID LIQUID EXTRACTION; METHODOLOGY; TANDEM MASS SPECTROMETRY;

ALKALOIDS; ANIMALS; CENTRAL NERVOUS SYSTEM STIMULANTS; DESIGNER DRUGS; DOPING IN SPORTS; HORSES; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIMIT OF DETECTION; LIQUID-LIQUID EXTRACTION; METHYL ETHERS; TANDEM MASS SPECTROMETRY;

EID: 84890530153     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.6778     Document Type: Article

References (56)

1. D. M. Wood, S. Davies, S. L. Greene, J. Button, D. W. Holt, J. Ramsey, P. I. Dargan,. Case series of individuals with analytically confirmed acute mephedrone toxicity. Clin. Toxicol. (Phila.) 2010, 48, 924.
2. P. D. Maskell, G. D. Paoli, C. Seneviratne, D. J. Pounder,. Mephedrone (4-methylmethcathinone)-related deaths. J. Anal. Toxicol. 2011, 35, 188.
3. I. Vardakou, C. Pistos, C. Spiliopoulou,. Spice drugs as a new trend: mode of action, identification and legislation. Toxicol. Lett. 2010, 197, 157.
4. H. Torrance, G. Cooper,. The detection of mephedrone (4- methylmethcathinone) in 4 fatalities in Scotland. Forensic Sci. Int. 2010, 202, e62.
5. P. Nencini,. Cathinone, active principle of the khat leaf: its effects on in vivo and in vitro lipolysis. Pharmacol. Res. Commun. 1980, 12, 855.
6. M. Odenwald, N. Warfa, K. Buhl, T. Elbert,. The stimulant khat-another door in the wall? A call for overcoming the barriers. J. Ethnopharmacol. 2010, 132, 615.
7. A. Klein, P. Metal,. A good chew or good riddance-how to move forward in the regulation of khat consumption. J. Ethnopharmacol. 2010, 132, 584.
8. K. Szendrei,. The chemistry of khat. Bull. Narcotics 1980, 32, 5.
9. European Monitoring Center for Drugs and Drug Addiction (EMCDDA), Synthetic cathinones. http://www.emcdda,europa.eu/publications/drug.profiles/ synthetic.cathinones (accessed May 2, 2013).
10. N. V. Cozzi, M. K. Sievert, A. T. Shulgin, P. Jacob III, A. E. Ruoho,. Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines. Eur. J. Pharmacol. 1999, 381, 63.
11. J. M. Prosser, S. Nelson,. The toxicology of bath salts: a review of synthetic cathinones. J. Med. Toxicol. 2012, 8, 33.
12. D. Kebede, A. Alem, G. Mitike, F. Enquselassie, F. Berhane, Y. Abebe, R. Ayele, W. Lemma, T. Assefa, T. Gebremichael,. Khat and alcohol use and risky sex behavior among in-school and out-of-school youth in Ethiopia. BMC Public Health 2005, 5, 109.
13. V. C. Freund-Michel, M. A. Birrell, H. J. Patel, I. M. Murray-Lyon, M. G. Belvisi,. Modulation of cholinergic contractions of airway smooth muscle by cathinone; potential beneficial effects in airway diseases. Eur. Respir. J. 2008, 32, 579.
14. C. D. Murphy, C. W. Le Roux, A. V. Emmanuel, J. M. Halkaet, A. M. Przyborrowska, M. A. Kamm, I. M. Murray-Lyon,. The effect of khat (Catha edulis) as an appetite suppressant is independent of ghrelin and PYY secretion. Appetite 2008, 51, 747.
15. S. Gardos, J. O. Cole,. Evaluation of pyrovalerone in chronically fatigued volunteers. Curr. Ther. Res. Clin. Exp. 1971, 13, 631.
16. H. A. Spiller, M. L. Ryan, R. G. Weston, J. Jansen,. Clinical experience with and analytical confirmation of 'bath salts' and 'legal highs' (synthetic cathinones) in the United States. Clin. Toxicol. (Phila.) 2011, 49, 499.
17. Department of Justice, Drug Enforcement Administration. 21 CFR Part 1308. Fed. Reg. 2011, 76, 204.
18. S. Strano-Rossi, A. B. Cadwallader, X. de la Torre, F. Botrè,. Toxicological determination and in vitro metabolism of the designer drug methylenedioxypyrovalerone (MDPV) by gas chromatography/mass spectrometry and liquid chromatography/quadrupole time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 2010, 24, 2076.
19. M. R. Meyer, C. Vollmar, A. E. Schwaninger, E. Wolf, H. H. Maurer,. New cathinone-derived designer drugs 3-bromomethcathinone and 3-fluoromethcathinone: studies on their metabolism in rat urine and human liver microsomes using GC-MS and LC-high-resolution MS and their detectability in urine. J. Mass Spectrom. 2012, 47, 253.
20. R. Brennelsen, H. U. Fisch, U. Koelbing, S. Geischuler, P. Kalix,. Amphetamine-like effects in humans of the khat alkaloid cathinone. Br. J. Clin. Pharmacol. 1990, 30, 825.
21. P. Widler, K. Mathys, R. Brennelsen, P. Kalix, H. U. Fisch,. Pharmacodynamics and pharmacokinetics of khat: a controlled study. Clin. Pharmacol. Ther. 1994, 55, 556.
22. A. N. Guantai, C. K. Maitai,. Metabolism of cathinone to d-norpseudoephedrine in humans. J. Pharm. Sci. 1983, 72, 1217.
23. K. Mathys, R. Brennelsen,. Determination of (S)-(-)-cathinone and its metabolites (R,S)-(-)-norephedrine and (R,R)-(-)-norpseudoephedrine in urine by high-performance liquid chromatography with photoiode-array detection. J. Chromatogr. 1992, 593, 79.
24. G. Frison, M. Gregio, L. Zamengo, F. Zancanaro, S. Frasson, R. Sciarrone,. Gas chromatography/mass spectrometry determination of mephedrone in drug seizures after derivatization with 2,2,2-trichloroethyl chloroformate. Rapid Commun. Mass Spectrom. 2011, 25, 387.
25. S. D. Brandt, S. Freeman,. Analysis of NRG 'legal highs' in the UK: identification and formation of novel cathinones. Drug Test. Anal. 2011, 3, 569.
26. D. Zuba,. Identification of cathinones and other active components of 'legal highs' by mass spectrometric methods. Trends Anal. Chem. 2012, 32, 15.
27. P. Jankovics, A. Váradi, L. Tölgyesi, S. Lohner, J. Németh-Palotás, H. Koszegi-Szalai,. Identification and characterization of the new designer drug 4'- methylethcathinone (4-MEC) and elaboration of a novel liquid chromatography-tandem mass spectrometry (LC-MS/MS) screening method for seven different methcathinone analogs. Forensic Sci. Int. 2011, 210, 213.
28. C. Bell, C. George, A. T. Kickman, A. Traynor,. Development of a rapid LC-MS/MS method for direct urinalysis of designer drugs. Drug Test. Anal. 2011, 3, 496.
29. S. Strano-Rossi, L. Anzillotti, E. Castrignanò, F. S. Romolo, M. Chiarotti,. Ultra high performance liquid chromatography-electrospray ionization-tandem mass spectrometry screening method for direct analysis of designer drugs, « spice» and stimulants in oral fluid. J. Chromatogr. A 2012, 1258, 37.
30. D. Ammann, M. J. McLaren, D. Gerostamoulos, J. Beyer,. Detection and quantification of new designer drugs in human blood: Part 2-Designer cathinones. J. Anal. Toxicol. 2012, 36, 381.
31. R. E. Jamt, A. Gjelstad, L. E. Eibak, E.L. Øiestad, A. S. Christophersen, K. E. Rasmussen, S. Pedersen-Bjergaard,. Electromembrane extraction of stimulating drugs from undiluted whole blood. J. Chromatogr. A 2012, 1232, 27.
32. J. Beyer, F. T. Peters, T. Kraemer, H. H. Maurer,. Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization. J. Mass Spectrom. 2007, 42, 150.
33. S. R. Needham, P. R. Brown, K. Duff, D. Bell,. Optimized stationary phases for the high-performance liquid chromatography-electrospray ionization mass spectrometric analysis of basic pharmaceuticals. J. Chromatogr. A 2000, 869, 159.
34. T. M. Brunt, A. Poortman, R. J. Neisink, W. van den Brink,. Instability of the ecstasy market and a new kid on the block: mephedrone. J. Psychopharmacol. 2011, 25, 1543.
35. The state of the drugs problem in Europe. EMCDDA, Lisbon, Portugal, 2009. http://www.emcdda.europa.eu/attachements.cfm/att-93236-EN-EMCDDA-AR2009-EN.pdf (accessed May 2, 2013).
36. J. DeRuiter, L. Hayes, A. Valaer, C. R. Clark,. Methcathinone and designer analogues: synthesis, stereochemical analysis, and analytical properties. J. Chromatogr. Sci. 1994, 32, 552.
37. T. Yoshida, T. Okada,. Peptide separation in normal-phase liquid chromatography. Study of selectivity and mobile phase effects on various columns. J. Chromatogr. A 1999, 840, 1.
38. K. Buck, P. Voehringer, B. Ferger,. Rapid analysis of GABA and glutamate in microdialysis samples using high performance liquid chromatography and tandem mass spectrometry. J. Neurosci. Methods 2009, 182, 78.
39. A. J. Alpert, A. K. Shukala, L. R. Zieskw, S. W. Yuen, M. A. J. Ferguson, A. Mehlert, M. Pauly, R. J. Orlando,. Hydrophilic-interaction chromatography of complex carbohydrates. J. Chromatogr. A 1994, 676, 191.
40. W. Jian, R. W. Edom, Y. Xu, N. Weng,. Recent advances in application of hydrophilic interaction chromatography for quantitative bioanalysis. J. Sep. Sci. 2010, 33, 681.
41. P. Li, W. D. Beck, P. M. Callahan, A. V. Terry Jr, M. G. Bartlett,. Quantitation of cotinine and its metabolites in rat plasma and brain tissue by hydrophilic interaction chromatography tandem mass spectrometry (HILIC-MS/MS). J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2012, 907, 117.
42. P. Nencini, A. M. Ajmed,. Khat consumption: a pharmacological review. Drug Alcohol Depend. 1989, 23, 19.
43. N. B. Patel,. Mechanism of action of cathinone: the active ingredient of khat (Catha edulis). East Afr. Med. J. 2000, 77, 329.
44. J. S. Chappell, M. M. Lee,. Cathinone preservation in khat evidence via drying. Forensic Sci. Int. 2010, 195, 108.
45. S. Gibbons, M. Zloh,. An analysis of the 'legal high' mephedrone. Bioorg. Med. Chem. Lett. 2010, 20, 4135.
46. A.J. Albert,. Hydrophilic-interaction chromatography for the separation of peptides, nucleic acids and other polar compounds. J. Chromatogr. A 1990, 499, 177.
47. P. Hemstrom, K. Irgum,. Hydrophilic interaction chromatography. J. Sep. Sci. 2006, 29, 1784.
48. Y. Guo, S. Gaiki,. Retention behavior of small polar compounds on polar stationary phases in hydrophilic interaction chromatography. J. Chromatogr. A 2005, 1074, 71.
49. P. Jandera,. Stationary phases for hydrophilic interaction chromatography, their characterization and implementation into multidimensional chromatography concepts. J. Sep. Sci. 2008, 31, 1421.
50. D. V. McCalley,. Is hydrophilic interaction chromatography with silica columns a viable alternative to reversed-phase liquid chromatography for the analysis of unstable compounds? J. Chromatogr. A 2007, 1171, 46.
51. N. Weng,. Bioanalytical liquid chromatography tandem mass spectrometry methods on underivatized silica columns with aqueous/organic mobile phases. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2003, 796, 209.
52. M. Storton, J. Exarchalkkis, T. Waters, Z. Hao, B. Parker, M. Knapp,. Lactic acid quantitation in hand dishwashing liquid using an HILIC-UV methodology. J. Sep. Sci. 2010, 33, 982.
53. U.S. Food and Drug Administration. Guidance for Industry Bioanalytical Method Validation. Available: http://www.fda.gov/downloads/Drugs/Guidances/ ucm070107.pdf.
54. Y. Liu, C. E. Uboh, L. R. Soma, X. Li, F. Guan, Y. You, J. W. Chen,. Efficient use of retention time for the analysis of 302 drugs in equine plasma by liquid chromatography-MS/MS with scheduled multiple reaction monitoring and instant library searching for doping control. Anal. Chem. 2011, 83, 6834.
55. F. Westphal,., T. Junge, P. Pösner, F. Sönnichsen, F. Schuster,. Mass and NMR spectroscopic characterization of 3,4- methylenedioxypyrolvalerone a designer drug with a pyrrolidinophenone structure. Forensic Sci. Int. 2009, 190, 1.
56. L. K. Sørensen,. Determination of cathinones and related ephedrines in forensic whole-blood samples by liquid-chromatography-electrospray tandem mass spectrometry. J. Chromatogr. B 2011, 879, 727.