Determination of tuaminoheptane in doping control urine samples

European Journal of Mass Spectrometry

Volumn 13, Issue 3, 2007, Pages 213-221

  Thevis, Mario ^a   Sigmund, Gerd ^a   Koch, Anja ^a   Schänzer, Wilhelm ^a  

^a GERMAN SPORT UNIVERSITY COLOGNE   (Germany)

Author keywords

Amine; Gas chromatography; Mass spectrometry; Sport; Stimulant

Indexed keywords

DECONGESTIVE AGENT; HEPTANE;

ARTICLE; DOPING; HUMAN; MASS FRAGMENTOGRAPHY; METHODOLOGY; REPRODUCIBILITY; SENSITIVITY AND SPECIFICITY; SUBSTANCE ABUSE; URINALYSIS; URINE;

DOPING IN SPORTS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HEPTANES; HUMANS; NASAL DECONGESTANTS; REPRODUCIBILITY OF RESULTS; SENSITIVITY AND SPECIFICITY; SUBSTANCE ABUSE DETECTION; URINALYSIS;

EID: 34748826883     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.875     Document Type: Article

References (42)

1. J.E.F. Reynolds, Martindale - The Extra Pharmacopoeia. The Pharmaceutical Press, London. UK (2002).
2. Documed, "Arzneimittel-Kompendium der Schweiz", www.kompendium.ch/MonographieTxt.aspx?lang=de&MonType=fi, 30.1.2007.
3. D. Klaus, "Treatment of hypotensive regulation disorders", Internist Prax 17, 438 (1977).
4. D.A. Durden, L.E. Dyck, B.A. Davis, Y.D. Liu and A.A. Boulton, "Metabolism and pharmacokinetics, in the rat, of (R)-N-(2-Heptyl)Methyl- propargylamine (R-2HMP), a new potent monoamine oxidase inhibitor and antiapoptotic agent", Drug Metab. Dispos. 28, 147 (2000).
5. World Anti-Doping Agency, "The 2007 Prohibited List", http://www.wada-ama.org/rtecontent/document/2007_List_ En.pdf, 30-01-2007
6. E. Brochmann-Hanssen and A.B. Svendsen, "Separation and identification of sympathomimetic amines by gas-liquid chromatography", J. Pharm. Sci. 51, 938 (1962). doi: 10.1002/ jps.2600511007
7. E. Brochmann-Hanssen and A.B. Svendsen, "Gas chromatography of sympathomimetic amines", J. Pharm. Sci. 51, 393 (1962). doi: 10.1002/jps.2600510427
8. J. Pietsch, S. Hampel, W. Schmidt, H.J. Brauch and E. Worch, "Determination of aliphatic and alicyclic amines in water by gas and liquid chromatography after derivatization by chloroformates", Anal. Bioanal. Chem. 355, 164 (1996). doi: 10.1007/s0021663550164
9. K. Ohta, A. Towata, M. Ohashi and T. Takeuchi, "Separation and conductimetric detection of C1-C7 aliphatic monocarboxylic acids and C1-C7 aliphatic monoamines on unfunctionized polymethacrylate resin columns", J. Chromatogr. A 1039, 171 (2004). doi: 10.1016/j.chroma.2003.12. 066
10. M. Thevis and W. Schänzer, "Mass Spectrometry in Doping Control Analysis", Curr. Org. Chem. 9, 825 (2005). doi: 10.2174/1385272054038318
11. M. Thevis and W. Schänzer, "Mass spectrometry in sports drug testing: Structure characterization and analytical assays", Mass Spectrom. Rev. 26, 79 (2007). doi: 10.1002/ mas.20107
12. E. Nolteernsting, G. Opfermann and M. Donike, in Recent Advances in Doping Analysis, Vol. 3, Ed by M. Donike, H. Geyer, A. Gotzmann and U. Mareck-Engelke. Sport&Buch Strauss, Cologne, Germany, p. 369 (1996).
13. 2-agonists in human or equine urine", J. Mass Spectrom. 38, 1197 (2003). doi: 10.1002/jms.542
14. G.J. Dutton, Glucuronidation of Drugs and Other Compounds. CRC Press, Boca Raton, Florida, USA (1980).
15. C.A. Marsh, in Glucuronic Acid - free and combined, Ed by G.J. Dutton. Academic Press, New York, USA, p. 3 (1966).
16. M. Donike, L. Jaenicke, D. Stratmann and W. Hollmann, "Gas Chromatographic detection of Nitrogen-Containing Drugs in Aqueous Solutions by Means of the Nitrogen Detector", J. Chromatogr. 52, 237 (1970).
17. M. Donike and J. Derenbach, "Die Selektive Derivatisierung Unter Kontrollierten Bedingungen: Ein Weg zum Spurennachweis von Aminen", Z. Anal. Chem. 279, 128 (1976). doi: 10.1007/BF00440797
18. M. Donike, "Acylierung mit Bis(Acylamiden); N-Methyl- Bis(Trifluoracetamid) und Bis(Trifluoracetamid), zwei neue Reagenzien zur Trifluoracetylierung", J. Chromatogr. 78, 273 (1973).
19. J.T. Cody, "Determination of methamphetamine enantiomer ratios in urine by gas chromatography-mass spectrometry", J. Chromatogr. 580, 77 (1992). doi: 10.1016/0378-4347(92)80529-Y
20. F.T. Delbeke, M. Debackere, J.A. Jonckheere and A.P. De Leenheer, "Pentafluorobenzoyl derivatives of doping agents. I. Extractive benzoylation and gas chromatography with electron-capture detection of primary and secondary amines", J. Chromatogr. 273, 141 (1983). doi: 10.1016/S0378-4347(00)80930-5
21. A.H. Beckett, G.T. Tucker and A.C. Moffat, "Routine Detection and Identification in Urine of Stimulants and Other Drugs, Some of Which May be Used to Modify Performance in Sport", J. Pharm. Pharmacol. 19, 273 (1967).
22. J.L. Valentine and R. Middleton, "GC-MS identification of sympathomimetic amine drugs in urine: rapid methodology applicable for emergency clinical toxicology", J. Anal. Toxicol. 24, 211 (2000).
23. H.S. Shin and M. Donike, "Stereospecific derivatization of amphetamines, phenol alkylamines and hydroxyamines and quantification of the enantiomers by capillary GC/MS", Anal. Chem. 68, 3015 (1996). doi: 10.1021/ac960365v
24. T. Gunnar, K. Ariniemi and P. Lillsunde, "Validated toxicological determination of 30 drugs of abuse as optimized derivatives in oral fluid by long column fast gas chromatography/ electron impact mass spectrometry", J. Mass Spectrom. 40, 739 (2005). doi: 10.1002/jms.846
25. D.A. Durden, B.A. Davis and A.A. Boulton, "Enantioselective gas chromatographic assay of 2-alkylamines using N-(trifluoroacetyl)prolyl derivatives and a chiral capillary column", J. Chromatogr. B 689,165 (1997). doi: 10.1016/S0378-4347(96)00397-0
26. A. Kromidas, Validierung in der Analytik. Wiley-VCH, Weinheim, Germany (1999).
27. J. Mandel, The Statistical Analyses of Experimental Data. John Wiley & Sons, New York, USA (1964).
28. R.S. Gohlke and F.W. McLafferty, "Mass Spectrometric Analysis - Aliphatic Amines", Anal. Chem. 34, 1281 (1962). doi: 10.1021/ac60190a025
29. S. Hammerum, "Distonic Radical Cations in Gaseous and Condensed Phase", Mass Spectrom. Rev. 7, 123 (1988). doi: 10.1002/mas.1280070202
30. S. Hammerum, "Rearrangement and hydrogen abstraction reactions of amine cation radicals - a gas-phase analogy to the Hofmann-Löffler-Freytag reaction". Tetrahedron Lett. 22, 157 (1981). doi: 10.1016/0040-4039(81)80175-X
31. S. Hammerum and C.B. Nielsen, "Intramolecular hydrogen bonding and hydrogen atom abstraction in gas-phase aliphatic amine radical cations", J. Phys. Chem. A 109, 12046 (2005). doi: 10.1021/jp0550614
32. S. Hammerum and T. Henriksen, "The rearrangement and simple cleavage of metastable octanamine radical cations", Int. J. Mass Spectrom. 199, 79 (2000). doi: 10.1016/S1387-3806(00)00166-4
33. S. Hammerum, K. Norrman, T.I. Solling, P.E. Andersen, L.B. Jensen and T. Vulpius, "Competing simple cleavage reactions: the elimination of alkyl radicals from amine radical cations", J. Am. Chem. Soc. 127, 6466 (2005). doi: 10.1021/ ja0434811
34. +• en phase gazeuse", Tetrahedron 42, 1179 (1986). doi: 10.1016/S0040-4020(01)87523-2
35. T. Barry and G. Petzinger, "Structure and fragmentation mechanisms of some ions in the mass spectrum of ephedrine", Biomed. Mass Spectrom. 4, 129 (1977). doi: 10.1002/ bms.1200040302
36. P. Hemmersbach and R. de la Torre, "Stimulants, narcotics and β-blockers: 25 years of development in analytical techniques for doping control", J. Chromatogr. B Biomed. Appl. 687, 221 (1996). doi: 10.1016/S0378-4347(96)00276-9
37. W. Gottwald, Statistik für Anwender. Wiley-VCH, Weinheim, Germany (2000).
38. M.D. Green and T.R. Tephly, "Glucuronidation of amine substrates by purified and expressed UDP-glucuronosyltransferase proteins", Drug Metab. Dispos. 26, 860 (1998).
39. A. Orzechowski, D. Schrenk and K.W. Bock, "Metabolism of 1- and 2-naphthylamine in isolated rat hepatocytes", Carcinogenesis 13, 2227 (1992). doi: 10.1093/ carcin/13.12.2227
40. A.G. Staines, M.W. Coughtrie and B. Burchell, "N- glucuronidation of carbamazepine in human tissues is mediated by UGT2B7", J. Pharmacol. Exp. Ther. 311, 1131 (2004). doi: 10.1124/jpet.104.073114
41. U. Mareck, H. Geyer, S. Guddat, N. Haenelt, A. Koch, M. Kohler, G. Opfermann, M. Thevis and W. Schänzer, "Identification of the aromatase inhibitors anastrozole and exemestane in human urine using liquid chromatography/tandem mass spectrometry", Rapid Commun. Mass Spectrom. 20, 1954 (2006). doi: 10.1002/rcm.2545
42. World Anti-Doping Agency, "Minimum Required Performance Limits for Detection of Prohibited Substances", http://www.wada-ama.org/rtecontent/ document/perf_limits_2.pdf, 06-02-2007