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Chemical Compound Review

Hempa     N- bis(dimethylamino)phosphoryl- N-methyl...

Synonyms: HMPTA, Hexametapol, HMPA, HMPT, PubChem13752, ...
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Disease relevance of Hexametapol


High impact information on Hexametapol


Chemical compound and disease context of Hexametapol


Biological context of Hexametapol


Anatomical context of Hexametapol

  • The ciliated cells of the airway epithelium were denuded, and microulcerative lesions in the epithelium were induced in the HMPA-treated rats [14].
  • Significant dose-dependent increases in DPXL formation were observed in respiratory and olfactory epithelial cells exposed to > or = 0.5 and 1 mM HMPA, respectively, for 3 h at 37 degrees C. This resulted in DPXL accumulation at 18-20% higher levels than untreated cells [15].
  • Both test chemicals produced a statistically significant increase (P 0.001) in the incidence of micronuclei in bone marrow cells in all strains at both sampling times but the response with HMPA in C57Bl/6J mice appears to occur earlier than in the other two strains [16].
  • Hexamethylphosphoramide (HMPA) is a rat nasal carcinogen that induces squamous cell carcinomas in the anterior portions of the nasal cavity following chronic inhalation exposures as low as 50 ppb [17].
  • Using a filter binding assay, we demonstrated that microsomal activation is necessary for HMPA-induced crosslink formation between plasmid DNA and calf thymus histones, presumably through metabolic N-demethylation of HMPA and the formation of formaldehyde [15].

Associations of Hexametapol with other chemical compounds

  • Rearrangements, mostly deletions, represented by far the most frequent type of mutational events induced by HMPA that are detected as vermilion mutations [7].
  • They provided lower frep-/frep+ indices than would be anticipated on the basis of their nucleophilic selectivity (MC, BCNU, Thio-TEPA) or were even inactive (FA, MCT, HMPA) in the Drosophila repair assay [12].
  • 3. The Fe-S core of component C was extruded by treating the protein with p-methoxybenzenethiol in hexamethyl phosphoramide/50mM-Tris/HCl buffer, pH 8.5 (4:1, v/v), under anaerobic conditions [18].
  • The reaction of fluorobenzene with Me3Si- anion (1) in HMPA at room temperature surprisingly affords o- and p-fluorotrimethylsilylbenzenes (substitution of aromatic H for TMS, 76% yield) 7a and 7b and also 14% of trimethylsilylbenzene (2) [19].
  • The response of 3 strains of mouse (C57Bl/6J, C3H/C57 hybrid and BALBC/CBA) to cyclophosphamide (75 mg/kg) and hexamethylphosphoramide (HMPA) (1.28 ml/kg) were compared in the micronucleus test [16].

Gene context of Hexametapol


Analytical, diagnostic and therapeutic context of Hexametapol


  1. Biochemical and cytotoxic actions of 3,6-dihydroxy-4,5-dimethylphthalaldehyde in sarcoma 180 cells. Newman, E.M., Sartorelli, A.C. Cancer Res. (1981) [Pubmed]
  2. Enhancement of natural and experimental respiratory mycoplasmosis in rats by hexamethylphosphoramide. Overcash, R.G., Lindsey, J.R., Cassel, G.H., Baker, H.J. Am. J. Pathol. (1976) [Pubmed]
  3. Metaplastic changes of nasal respiratory epithelium in rats exposed to hexamethylphosphoramide (HMPA) by inhalation. Lee, K.P., Trochimowicz, H.J. Am. J. Pathol. (1982) [Pubmed]
  4. Induction of nasal tumors in rats exposed to hexamethylphosphoramide by inhalation. Lee, K.P., Trochimowicz, H.J. J. Natl. Cancer Inst. (1982) [Pubmed]
  5. Deuterium-labeling and NMR study of the dearomatization of N-alkyl-N-benzyldiphenylphosphinamides through anionic cyclization: ortho and benzylic lithiation directed by complex-induced proximity effects. Fernández, I., González, J., López-Ortiz, F. J. Am. Chem. Soc. (2004) [Pubmed]
  6. Immunochemical characterization of multiple forms of cytochrome P-450 in rabbit nasal microsomes and evidence for tissue-specific expression of P-450s NMa and NMb. Ding, X.X., Coon, M.J. Mol. Pharmacol. (1990) [Pubmed]
  7. The cross-linking agent hexamethylphosphoramide predominantly induces intra-locus and multi-locus deletions in postmeiotic germ cells of Drosophila. Aguirrezabalaga, I., Nivard, M.J., Comendador, M.A., Vogel, E.W. Genetics (1995) [Pubmed]
  8. Baculovirus-mediated expression and characterization of rat CYP2A3 and human CYP2a6: role in metabolic activation of nasal toxicants. Liu, C., Zhuo, X., Gonzalez, F.J., Ding, X. Mol. Pharmacol. (1996) [Pubmed]
  9. Characterization and stability of hydrogenase from Chromatium. Strekas, T., Antanaitis, B.C., Krasna, A.I. Biochim. Biophys. Acta (1980) [Pubmed]
  10. Detection of postural cerebral hypoperfusion with technetium-99m-HMPAO brain SPECT in patients with cerebrovascular disease. Hayashida, K., Hirose, Y., Kaminaga, T., Ishida, Y., Imakita, S., Takamiya, M., Yokota, I., Nishimura, T. J. Nucl. Med. (1993) [Pubmed]
  11. Formaldehyde generators: relationship between stability, lipophilicity and carcinogenic potency. Ashby, J., Lefevre, P.A. Carcinogenesis (1982) [Pubmed]
  12. Nucleophilic selectivity of carcinogens as a determinant of enhanced mutational response in excision repair-defective strains in Drosophila: effects of 30 carcinogens. Vogel, E.W. Carcinogenesis (1989) [Pubmed]
  13. Synthesis of [ethylene-1-(eta(5)-4,5,6,7-tetrahydro-1-indenyl)-2- (eta(5)-4',5',6',7'-tetrahydro-2'-indenyl)]titanium dichloride, the elusive isomer of the Brintzinger-type ansa-titanocenes. Kelly, P.A., Berger, G.O., Wyatt, J.K., Nantz, M.H. J. Org. Chem. (2003) [Pubmed]
  14. Chronic colonization of rat airways with Pseudomonas aeruginosa. Boyd, R.L., Ramphal, R., Rice, R., Mangos, J.A. Infect. Immun. (1983) [Pubmed]
  15. DNA-protein crosslink formation in rat nasal epithelial cells by hexamethylphosphoramide and its correlation with formaldehyde production. Kuykendall, J.R., Trela, B.A., Bogdanffy, M.S. Mutat. Res. (1995) [Pubmed]
  16. A comparison of the incidence of micronuclei in blood and bone marrow in 3 strains of mouse dosed with cyclophosphamide or hexamethylphosphoramide (HMPA). Styles, J.A., Richardson, C.R., Burlinson, B. Mutat. Res. (1983) [Pubmed]
  17. Mitogenic responses of rat nasal epithelium to hexamethylphosphoramide inhalation exposure. Harman, A.E., Voigt, J.M., Frame, S.R., Bogdanffy, M.S. Mutat. Res. (1997) [Pubmed]
  18. Characterization of the second prosthetic group of the flavoenzyme NADH-acceptor reductase (component C) of the methane mono-oxygenase from Methylococcus capsulatus (Bath). Colby, J., Dalton, H. Biochem. J. (1979) [Pubmed]
  19. A novel type of nucleophilic substitution reactions on nonactivated aromatic compounds and benzene itself with trimethylsiliconide anions. Postigo, A., Rossi, R.A. Org. Lett. (2001) [Pubmed]
  20. Hexamethylphosphoric triamide as a solubilizing agent. Purification and reactivation of diglyceride kinase. König, B., Bohnenberger, E., Sandermann, H. FEBS Lett. (1981) [Pubmed]
  21. Nasal cytochrome P450 2A: identification, regional localization, and metabolic activity toward hexamethylphosphoramide, a known nasal carcinogen. Thornton-Manning, J.R., Nikula, K.J., Hotchkiss, J.A., Avila, K.J., Rohrbacher, K.D., Ding, X., Dahl, A.R. Toxicol. Appl. Pharmacol. (1997) [Pubmed]
  22. Fmoc SPPS using Perloza beaded cellulose. Englebretsen, D.R., Harding, D.R. Int. J. Pept. Protein Res. (1994) [Pubmed]
  23. Selection of an in vitro carcinogenicity test for derivatives of the carcinogen hexamethylphosphoramide. Ashby, J., Styles, J.A., Anderson, D. Br. J. Cancer (1977) [Pubmed]
  24. Gel filtration of protected peptides on sephadex G-50 in hexamethylphosphoramide containing 5% water. Galpin, I.J., Kenner, G.W., Ohlsen, S.R., Ramage, R. J. Chromatogr. (1975) [Pubmed]
  25. Negative ion fast atom bombardment mass spectrometry for native gangliosides using a neutral matrix. Isobe, R., Kawano, Y., Higuchi, R., Komori, T. Anal. Biochem. (1989) [Pubmed]
  26. Detection of human immunodeficiency virus-1 nucleic acid on inactivated filter paper disks by polymerase chain reaction and microtiter plate assay. Kunisada, T., Ando, S., Saito, K., Eshita, Y., Röder, W., Kruse, M., Müller, W.E., Ushijima, H. Microbiol. Immunol. (1994) [Pubmed]
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