Rapid and Sensitive Quantitative Analysis of Alkyl Phosphates in Urine after Organophosphate Poisoning

Journal of Analytical Toxicology

Volumn 28, Issue 4, 2004, Pages 242-248

  Kupfermann, N ^a   Schmoldt, Achim ^a,b   Steinhart, H ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

^b UNIVERSITY MEDICAL CENTER HAMBURG EPPENDORF   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

O,O DIETHYLDITHIOPHOSPHATE; O,O DIETHYLTHIOPHOSPHATE; O,O DIMETHYLDITHIOPHOSPHATE; O,O DIMETHYLPHOSPHATE; O,O DIMETHYLTHIOPHOSPHATE; ORGANOPHOSPHATE INSECTICIDE; PHOSPHATE; PHOSPHORIC ACID DIETHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; GAS CHROMATOGRAPHY; HUMAN; INTOXICATION; MASS SPECTROMETRY; METABOLITE; SOLID PHASE EXTRACTION; TOXICOKINETICS; URINE LEVEL;

EID: 2342559918     PISSN: 01464760     EISSN: None     Source Type: Journal    
DOI: 10.1093/jat/28.4.242     Document Type: Article

References (33)

1. D. Blair and H.R. Roderick. An improved method for the determination of urinary dimethyl phosphate. J. Agric. Food Chem. 24: 1221-1223 (1976).
2. C.D. Brokopp, J.L. Wyatt, and J. Gabica. Dialkyl phosphates in urine samples from pesticide formulators exposed to disulfoton and phorate. Bull. Environ. Contam. Toxicol. 26: 524-529 (1981).
3. C.G. Daughton, D.G. Crosby, R.L. Garnas, and D.P.H. Hsieh. Analysis of phosphorus-containing hydrolytic products of organophosphorus insecticides in water. J. Agric. Food Chem. 24: 236-241 (1976).
4. V. Drevenkar, B. Stengl, and Z. Fröbe. Microanalysis of dialkylphosphorus metabolites of organophosphorus pesticides in human blood by capillary gas chromatography and by phosphorus-selective and ion trap detection. Anal. Chim. Acta. 290: 277-286 (1994).
5. C.A. Franklin, R.A. Fenske, R. Greenhalgh, L. Mathieu, H.V. Denley, J.T. Leffingwell, and R.C. Spear. Correlation of urinary pesticide metabolite excretion with estimated dermal contact in the course of occupational exposure to guthion. J. Toxicol. Environ. Health 7: 715-731 (1981).
6. Z. Fröbe, B. Stengl, V. Drevenkar, and A. Deljac. Accumulation of dialkylphosphorus anions from water by ion exchange on modified XAD-4 resin. J. Chromatogr. Sci. 28: 269-273 (1990).
7. E.M. Lores, D.E. Bradway, and R.F. Moseman. Organophosphorus pesticide poisonings in humans: determination of residues and metabolites in tissues and urine. Arch. Environ. Health 23: 270-276 (1978).
8. M.T. Shafik, D. Bradway, and H.F. Enos. A cleanup procedure for the determination of low levels of alkyl phosphates, thiophosphates, and dithiophosphates in rat and human urine. J. Agric. Food Chem. 19: 885-889 (1971).
9. L.E. St. John and D.J. Lisk. Determination of hydrolytic metabolites of organophosphorus insecticides in cow urine using an improved thermionic detector. J. Agric. Food Chem. 16: 48-49 (1968).
10. Z. Vasilik, V. Drevenkar, V. Rumenjak, B. Stengl, and Z. Fröbe, Urinary excretion of diethylphosphorus metabolites in persons poisoned by quinalphos or chlorpyrifos. Arch. Environ. Contam. Toxicol. 22: 351-357 (1992).
11. C. Aprea, G. Sciarra, D. Orsi, P. Boccalon, P. Sartorelli, and E. Sartorelli. Urinary excretion of alkylphosphates in the general population (Italy). Sci. Total Environ. 177: 37-41 (1996).
12. V. Bardarov and M. Mitewa. High-performance liquid and gas chromatography of dialkylphosphates, dialkylthiophosphates and dialkyldithiophosphates as their pentafluorobenzyl derivatives. J. Chromatogr. 462: 233-241 (1989).
13. R.E. Baynes and J.M. Bowen. Toxikinetics of methyl parathion in lactating goats. J. Agric. Food Chem. 43: 1598-1604 (1995).
14. R.A. Fenske and J.T Leffingwell. Method for the determination of dialkyl phosphate metabolites in urine for studies of human exposure to malathion. J. Agric. Food Chem. 37: 995-998 (1989).
15. T.F. Moate, C. Lu, R.A. Fenske, R.M.A. Hahne, and D.A. Kalman. Improved cleanup and determination of dialkyl phosphates in the urine of children exposed to organophosphorus insecticides. J. Anal. Toxicol. 23: 230-236 (1999).
16. A. Miki, H. Tsuchihashi, K. Ueda, and M. Yamashita. Gas chromatographic determination and gas chromatographic-mass spectrometric determination of dialkyl phosphates via extractive pentafluorobenzylation using a polymeric phasetransfer catalyst. J. Chromatogr. 718: 383-389 (1995).
17. J. Hardt and J. Angerer. Determination of dialkyl phosphates in human urine using gas chromatography-mass spectrometry. J. Anal. Toxicol. 24: 678-684 (2000).
18. A.N. Oglobline, G.E. O'Donnell, R. Geyer, G.M. Holder, and B. Tattam. Routine gas chromatographic determination of dialkylphosphate metabolites in the urine of workers occupationally exposed to organophosphorus insecticides. J. Anal. Toxicol. 25: 153-157 (2001).
19. F.C. Churchill, D.N. Ku, and J.W. Miles. Gas-liquid chromatographic inlet block derivatization of organophosphorus pesticides and related dialkyl phosphorothioates. J. Agric. Food Chem. 26: 1108-1112 (1978).
20. R.P. Moody, C.A. Franklin, D. Riedel, N.I. Muir, R. Greenhalgh, and A. Hladka. A new GC on-column methylation procedure for analysis of DMTP (O,O-dimethyl phosphorothioate) in urine of workers exposed to fenitrothion. J. Agric. Food Chem. 33: 464-467 (1985).
21. E.R. Richardson and J.N. Seiber. Gas chromatographic determination of organophosphorus insecticides and their dialkyl phosphate metabolites in liver and kidney samples. J. Agric. Food Chem. 41: 416-422 (1993).
22. S.S. Park, H. Pyo, K.-J. Lee, S.-J. Park, and T.K. Park. The analysis of common metabolites of organophosphorus pesticides in urine by gas chromatography/mass spectrometry. Bull. Korean Chem. Soc. 19: 45-50 (1998).
23. D.Y. Takade, J.M. Reynolds, and J.H. Nelson. 1-(4-Nitrobenzyl)-3-(4-tolyl)triazene as a derivatizing reagent for the analysis of urinary dialkyl phosphate metabolites of organophosphorus pesticides by gas chromatography. J. Agric. Food Chem. 27: 746-753 (1979).
24. R. Bravo, W.J. Driskell, R.D. Whitehead Jr., L.L. Needham, and D.B. Barr. Quantitation of dialkyl phosphate metabolites of organophosphate pesticides in human urine using GC-MS-MS with isotopic internal standards. J. Anal. Toxicol. 26: 245-252 (2002).
25. 14C-methyl] dichlorvos in the rat and mouse. Xenobiotica 2: 107-116 (1972).
26. H. Teichmann and G. Hilgetag. Zur Alkylierung des Thioharnstoffs mit Phosphorsäumestern. J. Praktische Chemie 16(4): 45 (1962).
27. E.I. Hoegberg and J.T. Cassaday. The reaction of O,O-dialkylthiophosphoric acid salts with some haloacyl derivatives. J. Am. Chem. Soc. 73: 557-559 (1951).
28. O. Foss. Di-O-alkylmonothiophosphates and di-alkylmonoselenophosphates and the corresponding pseudohalogenes. Acta Chem. Scand 1: 8-31 (1947).
29. X. Creary. Tosylhydrazone salt pyrolyses: phenyldiazomethanes. In Organic Synthesis, Vol. 64, A.S. Kende, Ed. John Wiley and Sons, New York, NY, 1986, pp 207-216.
30. D.S. Wulfman. The synthesis of aryl diazomethanes. Syn. Commun. 18: 2349-2352 (1988).
31. A. Jonczyk and J. Wlostowska. A simple method for generation of diazo compounds in an aqueous two-phase system. Syn. Commun. 8: 569-572 (1978).
32. C.C. Dudman and C.B. Reese. Preparation of aryldiazoalkanes from 2,4,6-triisopropylbenzenesulphonyl hydrazones. Synthesis 8: 419-421 (1982).
33. T. Shafik, D.E. Bradway, H.F. Enos, and A.R. Yobs. Human exposure to organophosphorus pesticides. A modified procedure for the gas-liquid chromatographic analysis of alkyl phosphate metabolites in urine. J. Agric. Food Chem. 21: 625-629 (1973).