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Chemical Compound Review

Naphthalidine     naphthalen-1-amine

Synonyms: Naphthalidam, Naphthylamine, SureCN9029, PubChem23886, CCRIS 423, ...
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Disease relevance of alpha-Naphthylamine

  • Gentamicin, kanamycin, and polymyxin B increased E. coli outer membrane permeability to the hydrophobic fluorescent compound 1-N-phenyl-naphthylamine (NPN) and the peptidoglycan-degrading enzyme lysozyme [1].
  • Some of the dogs receiving 1-naphthylamine (total dose 950 g) and the controls had focal cystitis or hyperplasia, but no neoplasia of the bladder [2].
  • In contrast with permeabilizers which are known to utilize the self-promoted uptake pathway, none of the quinolones studied permeabilized Gram-negative bacteria to lysozyme, caused enhanced fluorescence to 1-N-phenyl-naphthylamine (NPN) or increased the leakage of periplasmic beta-lactamase into the culture medium [3].
  • While all three toxicants produced perturbations in similar urinary metabolites, principal components analysis of the temporal progression identified that the rapid initial glycosuria associated with ANIT toxicity was also present with NI but not NA dosing [4].
  • Suramin, a polysulfonated naphthylamine, has been used for the chemotherapy of trypanosomiasis and onchocerciasis since about the 1920s [5].

High impact information on alpha-Naphthylamine

  • The rate of N-hydroxylation of 2-naphthylamine (2-NA) and 1-naphthylamine (1-NA) was compared in bovine bladder mucosa and was found to correlate well with the relative potency of these compounds as bladder carcinogens (4-BA greater than 2-NA greater than 1-NA) [6].
  • During the metaphase/anaphase transition, spindle membrane content remains constant, as evidenced by unchanging fluorescence with the hydrophobic probe, N-phenyl-1-naphthylamine (NPN) [7].
  • In addition, the hydrophobic fluorescent probe N-phenyl naphthylamine was rapidly embedded in the membranes of the SS-B strain but was poorly embedded in those of the parent strain [8].
  • To test this possibility, aqueous solutions of 1-naphthylamine (1-NA) were first exposed to air or O3 in the absence of cells and then used to treat cultured human lung cells, i.e., the diploid fibroblasts CCD-18Lu and the transformed type II epithelial cells A549 [9].
  • Significant decreases in BPD(-) glucuronidation activity (P < 0.02) were observed in subjects with the UGT1A1(*28/*28) genotype compared with subjects having the wild-type UGT1A1(*1/*1) genotype in assays of liver microsomes that included 0.1 mM alpha-naphthylamine, a competitive inhibitor of UGT1A9 and not UGT1A1 [10].

Chemical compound and disease context of alpha-Naphthylamine

  • In comparison with Fast Blue B and Fast Garnet GBC HP is a faster coupler, furnishes azodyes which are stable, amorphous (even without lipid extractions from sections), more substantive and in the case of 1-naphthylamine almost insoluble in ordinary lipid solvents used for the dehydration and clearing of sections before mounting [11].

Biological context of alpha-Naphthylamine


Anatomical context of alpha-Naphthylamine


Associations of alpha-Naphthylamine with other chemical compounds


Gene context of alpha-Naphthylamine


Analytical, diagnostic and therapeutic context of alpha-Naphthylamine

  • The incidence of bladder cancer in dogs fed mixtures of both naphthylamines explains why previous experimental and epidemiological studies of impure 1-naphthylamine have revealed carcinogenicity [2].
  • Soluble exopeptidases present in bovine and human lenses were identified and characterized using starch gel electrophoresis separation followed by activity staining with an L-aminoacid oxidase/peroxidase system or a naphthylamine fluorescence system [26].
  • Determination of naptalam and its metabolite in foods, as 1-naphthylamine, using liquid chromatography with oxidative electrochemical detection [14].
  • A rapid and sensitive high-performance liquid chromatographic (HPLC) assay for the determination of alpha-naphthylisothiocyanate (1-NITC) and two metabolites alpha-naphthylamine (1-NA) and alpha-naphthylisocyanate (1-NIC) in rat plasma and urine has been developed [27].


  1. Interaction of aminoglycosides with the outer membranes and purified lipopolysaccharide and OmpF porin of Escherichia coli. Hancock, R.E., Farmer, S.W., Li, Z.S., Poole, K. Antimicrob. Agents Chemother. (1991) [Pubmed]
  2. Lifetime carcinogenicity study of 1- and 2-naphthylamine in dogs. Purchase, I.F., Kalinowski, A.E., Ishmael, J., Wilson, J., Gore, C.W., Chart, I.S. Br. J. Cancer (1981) [Pubmed]
  3. Interaction of divalent cations, quinolones and bacteria. Marshall, A.J., Piddock, L.J. J. Antimicrob. Chemother. (1994) [Pubmed]
  4. Chemometric analysis of biofluids following toxicant induced hepatotoxicity: a metabonomic approach to distinguish the effects of 1-naphthylisothiocyanate from its products. Azmi, J., Griffin, J.L., Shore, R.F., Holmes, E., Nicholson, J.K. Xenobiotica (2005) [Pubmed]
  5. Teratogenic effects of suramin on the chick embryo. Männer, J., Seidl, W., Heinicke, F., Hesse, H. Anat. Embryol. (2003) [Pubmed]
  6. Organ, species, and compound specificity in the metabolic activation of primary aromatic amines. Poupko, J.M., Radomski, T., Santella, R.M., Radomski, J.L. J. Natl. Cancer Inst. (1983) [Pubmed]
  7. Ionic changes in the mitotic apparatus at the metaphase/anaphase transition. Wolniak, S.M., Hepler, P.K., Jackson, W.T. J. Cell Biol. (1983) [Pubmed]
  8. Antimicrobial susceptibility of Salmonella typhimurium carrying the outer membrane permeability mutation SS-B. Vaara, M. Antimicrob. Agents Chemother. (1990) [Pubmed]
  9. Induction of DNA damage in cultured human lung cells by tobacco smoke arylamines exposed to ambient levels of ozone. Kozumbo, W.J., Agarwal, S. Am. J. Respir. Cell Mol. Biol. (1990) [Pubmed]
  10. Correlation between the UDP-glucuronosyltransferase (UGT1A1) TATAA box polymorphism and carcinogen detoxification phenotype: significantly decreased glucuronidating activity against benzo(a)pyrene-7,8-dihydrodiol(-) in liver microsomes from subjects with the UGT1A1*28 variant. Fang, J.L., Lazarus, P. Cancer Epidemiol. Biomarkers Prev. (2004) [Pubmed]
  11. The use of hexazonium-p-rosanilin in the histochemical demonstration of peptidases. Lojda, Z. Histochemistry (1975) [Pubmed]
  12. Total synthesis of the calphostins: application of fischer carbene complexes and thermodynamic control of atropisomers. Merlic, C.A., Aldrich, C.C., Albaneze-Walker, J., Saghatelian, A., Mammen, J. J. Org. Chem. (2001) [Pubmed]
  13. The binding of a neutral aromatic molecule to a negatively-charged lipid membrane II. Kinetics and mechanism. Woolley, P., Diebler, H. Biophys. Chem. (1979) [Pubmed]
  14. Determination of naptalam and its metabolite in foods, as 1-naphthylamine, using liquid chromatography with oxidative electrochemical detection. Worobey, B.L., Shields, J.B. Journal - Association of Official Analytical Chemists. (1987) [Pubmed]
  15. 1H-NMR and protection studies of interactions between ligands and bovine pancreatic phospholipase A2. Williamson, M.P., Davis, P.D., Broadhurst, M.J., Nixon, J.S. Biochim. Biophys. Acta (1989) [Pubmed]
  16. Sodium hexametaphosphate sensitizes Pseudomonas aeruginosa, several other species of Pseudomonas, and Escherichia coli to hydrophobic drugs. Vaara, M., Jaakkola, J. Antimicrob. Agents Chemother. (1989) [Pubmed]
  17. Effects of interferon on natural killer (NK) cells assessed by fluorescent probes and flow cytometry. McGinnes, K., Chapman, G., Penny, R. J. Immunol. Methods (1988) [Pubmed]
  18. Biochemical interaction of human neutrophil peptide-1 with Mycobacterium tuberculosis H37Ra. Sharma, S., Verma, I., Khuller, G.K. Arch. Microbiol. (1999) [Pubmed]
  19. Brucella-Salmonella lipopolysaccharide chimeras are less permeable to hydrophobic probes and more sensitive to cationic peptides and EDTA than are their native Brucella sp. counterparts. Freer, E., Moreno, E., Moriyón, I., Pizarro-Cerdá, J., Weintraub, A., Gorvel, J.P. J. Bacteriol. (1996) [Pubmed]
  20. In vitro effects of organophosphorus compounds on calmodulin activity. Pala, I., Vig, P.J., Desaiah, D., Srinivasan, A. Journal of applied toxicology : JAT. (1991) [Pubmed]
  21. Specific aromatic amines as occupational bladder carcinogens. Clayson, D.B. National Cancer Institute monograph. (1981) [Pubmed]
  22. The selective serotonin reuptake inhibitor sertraline: its profile and use in psychiatric disorders. MacQueen, G., Born, L., Steiner, M. CNS drug reviews. (2001) [Pubmed]
  23. Cholesterol-lipid interactions in membranes. The saturation concentration of cholesterol in bilayers of various lipids. Reiber, H. Biochim. Biophys. Acta (1978) [Pubmed]
  24. Effect of various chemicals on the aldehyde dehydrogenase activity of the rat liver cytosol. Marselos, M., Vasiliou, V. Chem. Biol. Interact. (1991) [Pubmed]
  25. Histochemical and biochemical studies of dipeptidyl peptidase I (DPP I) in laboratory rodents. Gossrau, R. Acta Histochem. (1991) [Pubmed]
  26. Soluble exopeptidases of bovine and human lens: characterization by electrophoresis. Lafferty, M.A., Raducha, M., Harris, H. Curr. Eye Res. (1984) [Pubmed]
  27. Determination of alpha-naphthylisothiocyanate and metabolites alpha-naphthylamine and alpha-naphthylisocyanate in rat plasma and urine by high-performance liquid chromatography. Hu, K., Morris, M.E. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. (2003) [Pubmed]
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