Abstract
The addition of a nitroso group (−N=O) to a nitrogen atom is termed N-nitrosation: its product is an N-nitroso compound. These compounds include the nitrosamines (RR′−N−N=O), nitrosamides
, nitrosoureas
, and derivatives.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Freund, H. A. (1937). Clinical manifestations and studies in parenchymatous hepatitis. Ann. Intern. Med., 10, 1144
Hamilton, A. and Hardy, H. L. (1949). Industrial Toxicology. 2nd edn. p. 301. ( New York: Paul B. Hoeber, Inc. )
Barnes, J. M. and Magee, P. N. (1954). Some toxic properties of dimethylnitrosamine. Br. J. Ind. Med., 11, 167
Magee, P. N. and Barnes, J. N. (1956). The production of malignant primary hepatic tumors in the rat by feeding dimethylnitrosamine. Br. J. Cancer, 10, 114
Heath, D. F. (1962). The decomposition and toxicity of dialkylnitrosamines in rats. Biochem. J., 85, 72
Magee, P. N. and Hultin, T. (1962). Toxic liver injury and carcinogenesis. Biochem. J.„ 83, 106
Magee, P. N. and Farber, M. (1962). Toxic liver injury and carcinogenesis: methylation of rat liver nucleic acids by dimethylnitrosamine in vivo. Biochem. J., 83, 114
Hansen, M. A. (1964). An outbreak of toxic liver injury in ruminants. Nord. Vet. Med., 16, 323
Koppang, N. (1964). An outbreak of toxic liver injury in ruminants. Nord. Vet. Med., 16, 305
Ender, F., Havre, G., Helgebostad, A., Koppang, N., Madsen, R. and Cen, L. (1964). Isolation and identification of a hepatotoxic factor in herring meal produced from sodium nitrite preserved herring. Naturwissenschaften, 51, 637
Sakshaug, J., Sognen, E., Hansen, M. A. and Koppang, N. (1965). Dimethylnitrosamine; its hepatotoxic effect in sheep and its occurrence in toxic batches of herring meal, Nature (London), 206, 1261
Ender, F., Havre, G., Madsen, R., Ceh, L. and Helgebostad, A. (1967). Studies on conditions under which N-nitrosodimethylamine is formed in herring meal produced from nitrite preserved herring. The risk of using nitrite uncritically as a preservative agent. Tierphysiol. Tieremahr. Futtermittelk., 22, 181
Terracini, B., Magee, P. N. and Barnes, J. M. (1967). Hepatic pathology in rats on low dietary levels of dimethylnitrosamine. Br. J. Cancer, 21, 559
Crampton, R. F. (1980). Carcinogenic dose-related response to nitrosamines. Oncology, 37, 251
Diaz Gomez, M. I., Swann, P. E. and Magee, P. N. (1977). The absorption and metabolism in rats of small oral doses of dimethylnitrosamine. Biochem. J., 164, 497
Pegg, A. E. and Hui, G. (1978). Formation and subsequent removal of O6-methylguanine from deoxyribonucleic acid in rat liver and kidney after small doses of dimethylnitrosamine. Biochem. J., 173, 739
Montesano, R. and Magee, P. N. (1970). Metabolism of dimethylnitrosamine by human liver slices in vitro. Nature (London), 228, 173
Magee, P. N., Montesano, R. and Preussmann, R. (1976). N-Nitroso compounds and related carcinogens. In Searle, C. E. (ed.) Chemical Carcinogens, pp. 491–625. American Chemical Society Monograph 173, ( Washington: American Chemical Society )
International Agency for Research on Cancer Working Group (1978). Some N-Nitroso Compounds. I ARC Pub. No. 17 ( Lyon: I ARC )
Mirvish, S. S. (1975). Formation of N-nitroso compounds: chemistry, kinetics and in vivo occurrence. Toxicol. Appl. Pharmacol, 31, 325
Druckrey, H., Preussmann, R., Ivankovic, S. and Schmahl, D. (1967). Organotrope carcinogene Wirkungen bei 65 venschildenen N-nitroso-verbindungen an BD-ratten. Z. Krebsforsch., 69, 103
Ridd, J. H. (1961). Nitrosation, diazotisation and deamination. Q. Rev. Chem. Soc., (London), 15, 418
Mirvish, S. S. (1970). Kinetics of dimethylamine nitrosation in relation to nitrosamine carcinogenesis. J. Natl. Cancer Inst., 44, 633
Lijinsky, W., Keefer, L., Conrad, E. and Van de Bogart, R. (1972). Nitrosation of tertiary amines and some biologic implications. J. Natl. Cancer Inst., 49, 1239
Lijinsky, W. and Breenblatt, M. (1972). Carcinogen dimethylnitrosamine produced in vivo from nitrite and aminopyrine. Nature New Biol., 236, 177
Fiddler, W., Pensabene, J. W., Doerr, R. C. and Wasserman, A. E. (1972). Formation of N-nitrosodimethylamine from naturally occurring quaternary ammonium compounds and tertiary amines. Nature (London), 236, 307
Obiedzinski, M. W., Wishnok, J. S. and Tannenbaum, S. R. (1980). N-Nitroso compounds from reactions of nitrite with methylamine. Food Cosmet. Toxicol (In press)
Scanlan, R. A. (1975). iV-Nitrosamines in foods. Crit. Rev. Food Technol, 5, 357
Fan, T. Y. and Tannenbaum, S. R. (1973). Factors influencing the rate of formation of nitrosomorpholine from morpholine and nitrite: Acceleration by thiocyanate and other anions. J. Agr. Food Chem., 21, 237
Keefer, L. K. and Roller, P. P. (1973). N-Nitrosation by nitrite ion in neutral and basic medium. Science, 181, 1245
Archer, M. C., Tannenbaum, S. R. and Wishnok, J. S. (1976). Nitrosamine formation in the presence of carbonyl compounds. In Environmental N-Nitroso Compounds Analysis and Formation. IARC Sci. Pub. No. 14, pp. 141–145. ( Lyon: IARC )
Bogovski, P., Castegnaro, M., Pignatelli, B. and Walker, E. A. (1972). The inhibiting effect of tannins on the formation of nitrosamines. In Bogovski, P., Preussmann, R. and Walker, E. A. (eds.) N-Nitroso Compounds: Analyses and Formation. IARC Sci. Pub. No. 3, pp. 127–129. ( Lyon: IARC )
Challis, B. C. (1973). Rapid nitrosation of phenols and its implications for health hazards from dietary nitrites. Nature (London), 244, 466
Davies, R. and McWeeny, D. J. (1977). Catalytic effect of nitrosophenols on N-nitrosamine formation. Nature (London), 266, 657
Challis, B. C. and Kyrtopoulos, S. A. (1979). Nitrosation of Amines by the Two Phase Interaction of Amines in Solution with Gaseous Oxides of Nitrogen. J. Chem. Soc. Perkins Trans. I, 299
Mirvish, S. S., Wallcave, L., Eagen, M. and Shubik, P. (1972). Ascorbate-nitrite reaction: Possible means of blocking the formation of carcinogenic N-nitroso compounds. Science, 177, 65
Tannenbaum, S. R. and Mergens, W. (1980). Reaction of nitrite with vitamins C and E. Presented at Conference on Micro-nutrient Interactions: Vitamins, Minerals and Hazardous Elements, The New York Academy of Sciences, NY (In press)
Invankovic, S., Preussmann, R., Schmahl, D. and Zeller, J. (1974). Prevention by ascorbic acid of in vivo formation of N-nitroso compounds. In Bogovski, P., Walker, E. A. and Davis, W. (eds.) N-Nitroso Compounds in the Environment. IARC Sci. Pub. No. 9, pp. 101–102. ( Lyon: IARC )
Mirvish, S. S., Cardesa, A., Wallcave, L. and Shubik, P. (1973). Effect of sodium ascorbate on lung adenoma induction by amines plus nitrite. Proc. Am. Assoc. Cancer Res., 14, 102
Fiddler, W., Pensabene, J. W., Piotrowski, E. G., Doerr, R. C. and Wasserman, A. E. (1973). Use of sodium ascorbate or erythorbate to inhibit formation of N-nitrosodimethylamine in frankfurters. J. Food Sci., 38, 1084
Sen, N. P. and Donaldson, B. (1974). The effect of ascorbic acid and glutathione on the formation of nitrosopiperazines from piperazine adipate and nitrite. In Bogovski, P., Walker, E. A. and Davis, W. (eds.) N-Nitroso Compounds in the Environment. IARC Sci. Pub. No. 9, pp. 103–106. ( Lyon: IARC )
Kamm, J. J., Dashman, T., Kewmark, H. and Megens, W. J. (1977). Inhibition of amine-nitrite hepatotoxicity by α-Tocopherol. Toxicol. Appl. Pharmacol., 41, 575
Tannenbaum, S. R., Moran, D., Rand, W., Cuello, C. and Correa, P. (1979). Gastric cancer in Colombia. IV. Nitrite and other ions in gastric contents of residents from a high-risk region. J. Natl Cancer Inst., 62, 9
Walters, C. L., Hill, M. J. and Ruddell, W. S. (1978). Gastric juice nitrite: its source and relationship to hydrogen ion concentration. In Walker, E. A., Castegnaro, M., Briciute, L. and Lyle, R. E. (eds.) Environmental Aspects of N-Nitroso Compounds. IARC Sci. Pub. No. 19, pp. 279–288. ( Lyon: IARC )
Sander, J. (1967). Kann Nitrit in der menschlichen Nahrung Ursache einer Krebsenstenhung durch Nitrosaminbildung sein? Arch. Hyg. Baku, 151, 22
Fine, D. H., Ross, R., Rounbehler, D. P., Silvergleid, A. and Song, L. (1977). Formation in vivo of volatile N-nitrosamines in man after ingestion of cooked bacon and spinach. Nature (London), 265, 753
Lakritz, L., Simenhoff, M. L., Dunn, S. R. and Fiddler, W. (1980). N-Nitrosodimethylamine in human blood. Food Cosmet. Toxicol., 18, 77
Sen, N. P., Smith, D. C. and Schwinghamer, L. (1969). Formation of N-nitrosamines from secondary amines and nitrite in human and animal gastric juice. Food Cosmet. Toxicol, 7, 301
Golovnya, R. V. (1976). Analysis of volatile amines contained in foodstuffs as possible precursors of iV-nitroso compounds. In Walker, E. A. and Bogovski, P. (eds.) Environmental N-Nitroso Compounds Analyses and Formation. IARC Pub. No. 14, pp. 237–245. ( Lyon: IARC )
Elespuru, R. K. and Lijinsky, W. (1973). Formation of carcinogenic nitroso compounds from nitrite and some types of agricultural chemicals. Food Cosmet. Toxicol., 11, 807
Eisenbrand, G., Unger, O. and Preussmann, R. (1974). Formation of N-nitroso compounds from agricultural chemicals and nitrite. In Bogovski, P., Walker, E. A. and Davis, W. (eds.) N-Nitroso Compounds in the Environment. IARC Sci. Pub. No. 9, pp. 71–74. ( Lyon: IARC )
Lijinsky, W. (1974). Reaction of drugs with nitrous acid as a source of carcinogenic nitrosamines. Cancer Res., 34, 255
Archer, M. C., Clark, S. D., Thilly, J. E. and Tannenbaum, S. R. (1971). Environmental nitroso compounds: Reaction of nitrite with creatine and creatinine. Science, 174, 1341
Endo, H., Takahashi, K. and Aoyagi, H. (1973). Identification and property of the mutagenic principle formed from a food component, methylguanidine, after nitrosation in simulated gastric juice. Biochem. Biophys. Res. Commun., 54, 1384
Knowles, M. E., McWeeney, D. J., Couchman, L. and Thorogood, M. (1974). Interaction of nitrite with proteins at gastric pH. Nature (London), 247, 288
Mohler, K. and Hallermayer, E. (1973). Buildung von Nitrosaminen aus Lecithin und Nitrit. Z. Lebensmitteluntersuch. Forsch., 151, 52
Bills, D. D., Hildrum, K. L, Scanlan, R. A. and Libbey, L. M. (1973). Potential precursors of N-nitrosopyrrolidine in bacon and other fried foods. Agr. Food Chem., 21 (5), 876
Pensabene, J. W., Fiddler, W., Gates, R. A., Fagan, J. C. and Wasserman, A. E. (1974). Effect of frying and other cooking conditions on nitrosopyrrolidine formation in bacon. J. Food Sci., 39, 314
Fiddler, W., Pensabene, J. W., Fagan, J. C., Thorne, E. J., Piotrowski, E. G. and Wasserman, A. E. (1974). The role of lean and adipose tissue on the formation of nitrosopyrrolidine in fried bacon. J. Food Sci., 39, 1070
Sen, N. P., Seaman, S. and Miles, W. F. (1976). Dimethylnitrosamine and nitrosopyrrolidine in fumes produced during the frying of bacon. Food Cosmet. Toxicol, 14, 167
Hansen, T., Iwaoka, W., Green, L. and Tannenbaum, S. R. (1977). Analysis of N-nitrosoproline in raw bacon. Further evidence that nitrosoproline is not a major precursor of nitrosopyrrolidine. J. Agric. Food Chem., 25 (6), 1423
Hwang, L. S. and Rosen, J. D. (1976). Nitrosopyrrolidine formation in fried bacon. J. Agric. Food Chem., 24, 1152
Spiegelhalder, B., Eisenbrand, G. and Preussmann, R. (1979). Contamination of beer with trace quantities of N-nitrosodimethylnitrosamine. Food Cosmet. Toxicol., 17, 29
Scanlan, R. A., Barbour, J. F., Hotchkiss, J. H. and Libbey, L. M. (1980). N-Nitrosodimethylamine in beer. Food Cosmet. Toxicol., 18, 27
Hotchkiss, J. H., Barbour, J. F. and Scanlan, R. A. (1980). Analysis of malted barley for N-nitrosodimethylamine. J. Agr. Food Chem., 28, 678
Preussman, R., Spiegelhalder, B. and Eisenbrand, G. (1980). Reduction of human exposure to environmental N-nitrosocarcinogens. Examples of possibilities for cancer prevention. Carcinogenesis: Fundamental Mechanisms and Environmental Effects, The 13th Jerusalem Symposium, Jerusalem, April 28–May 2, 1980 (In press)
Hoffmann, D., Rathkamp, C. and Liu, Y. Y. (1974). Chemical studies on tobacco smoke. XXVI. On the isolation and identification of volatile and nonvolatile N-nitrosamines and hydrazine in cigarette smoke. In Bogovski, P., Walker, E. A. and Davis, W. (eds.) N-Nitroso Compounds in the Environment. IARC Sci. Pub. No. 9, pp. 159–165. ( Lyon: IARC )
Brunneman, K. D. and Hoffman, D. (1978). Chemical studies on tobacco smoke. LIX. Analysis of volatile nitrosamines in tobacco smoke and polluted indoor environments. In Walker, E. A., Castegnaro, M., Griciute, L. and Lyle, R. E. (eds.) Environmental Aspects of N-nitroso Compounds, IARC Sci. Pub. No. 19, pp. 343–356. ( Lyon: IARC )
Archer, M. C. and Wishnok, J. S. (1976). Nitrosamine formation in corrosion-inhibiting compositions containing nitrite salts of secondary amines. J. Environ. Sci. Hlth., A11 (10 & 11), 583
Fan, T. Y., Morrison, J., Rounbehler, D. P., Ross, R. and Fine, D. H. (1977). N-nitrosodiethanolamine in synthetic cutting fluids: A part-per-hundred impurity. Science, 196, 70
Rappe, C. and Zingmark, P.-A. (1978) Formation of N-nitrosamines in cutting fluids. In Walker, E. A., Castegnaro, M., Griciute, L. and Lyle, R. E. (eds.) Environmental Aspects of N-Nitroso Compounds, IARC Sci. Pub. No. 19, pp. 213–217. ( Lyon: IARC )
Fajen, J. M., Carson, G. A., Rounbehler, D. P., Fan, T. Y., Vita, R., Goff, U. E., Wolf, M. H., Edwards, O. S., Fine, D. H., Reinhold, V. and Biemann, K. (1979). N-Nitrosamines in the rubber and tire industry. Science, 205, 1262
Pitts, J. N., Grosjean, D., VanCauwenberghe, K., Schmid, J. P. and Fitz, D. R. (1978). Photooxidation of aliphatic amines under simulated atmospheric conditions: formation of nitrosamines, nitramines, amides, and photochemical oxidant. Environ. Sci. Technol, 12, 946
Tannenbaum, S. R. (1980). A model for estimation of human exposure to endogenous N- nitrosodimethylamme, Oncology, 37, 232
Appel, B. R, Kothny, E. L., Hoffer, E. M., Hidy, G. M. and Wesolowsk, J. J. (1978). Sulfate and nitrate data from the California aerosol characterization experiment. Environ. Sci. TechnoL, 12, 418
Fishbein, L. (1976). Atmospheric mutagens. I. Sulfur oxides and nitrogen oxides. Mutation Res., 32, 309
National Research Council (1978). Nitrates: An Environmental Assessment ( Washington, DC: National Academy of Sciences )
White, J. W. (1975). Relative significance of dietary sources of nitrate and nitrite. J. Agric. Food Chem., 23, 886
White, J. W. (1976). Relative significance of dietary sources of nitrate and nitrite: correction. J. Agric. Food Chem., 24, 202
American Meat Institute Survey. (Personal communication, Dr J. Birdsall)
Cassens, R. G., Greaser, M. L., Ito, T. and Lee, M. (1979). Reactions of nitrite in meat. Food Technol., 33, 42
Miller, W. D. (1980). The Microorganisms of the Human Mouth, p. 364. ( Philadelphia: White )
Bokhoven, C. and Niessen, H. J. (1961). Amounts of oxides of nitrogen and carbon monoxide in cigarette smoke, with and without inhalation. Nature (London), 192, 458
Svorcova, S. and Kaut, V. (1971). Arteriovenous differences in the nitrite and nitrate ion concentrations in rabbits after inhalation of nitrogen oxides. Cesk. Hyg., 16, 71; (Chem. Abstr. 75, 33253 m)
Iqbal, Z. M., Dahl, K. and Epstein, S. S. (1980). Role of nitrogen dioxide in the biosynthesis of nitrosamines in mice. Science. 207, 1475
Schmidt, E. L. (1978). Nitrifying microorganisms and their methodology. In Schlessinger, D. (ed.) Microbiology, pp. 288–291. ( Washington, DC: American Society for Microbiology )
Hooper, A. B. (1978). Nitrogen oxidation and electron transport in ammonia oxidizing bacteria. In Schlessinger, D. (ed.) Microbiology, pp. 299–304. ( Washington, DC: American Society for Microbiology )
Ritchie, G. A. F. and Nicholas, D. J. D. (1972). Identification of the sources of nitrous oxide produced by oxidative and reductive processes in Nitrosomonas europaea. Biochem. J., 126, 1181
Nicholas, D. J. D. (1978). Intermediary metabolism of nitrifying bacteria with particular reference to nitrogen, carbon and sulfur compounds. In Schlessinger, D. (ed.) Microbiology. pp. 305–309. ( Washington, DC: American Society for Microbiology )
Rees, M. R. (1968). Studies of the hydroxylamine metabolism of Nitrosomonas europaea. Biochemistry 7, 366
Butt, W. D. and Lees, H. (1958). Cytochromes of Nitrobacter. Nature (London), 182, 732
Focht, D. D. and Verstraete, W. (1977), Biochemical ecology of nitrification and denitrification. Adv. Microbiol. Ecol. 1, 135
Obaton, M., Amarger, N. and Alexander, M. (1968). Heterotrophic nitrification of Pseudomonas aeruginosa. Arch. Mikrobiol., 63, 122
Verstraete, W. and Alexander, M. (1972). Heterotrophic nitrification by Arthrobacter sp. J. BacterioL, 110, 955
Weisburger, J. H. and Weisburger, E. K. (1973). Biochemical formation and pharmacological, toxieological, and pathological properties of hydroxylamine and hydroxamic acids. Pharmacol. Rev., 25, 1
Heubner, W. (1913). Studien uber methamoglobinbildung. Naunyn-Schmiedebergs Arch. Pharmakol. Exp. Pathol., 72, 241
Masters, B. S. S. and Ziegler, D. M. (1971). The distinct nature and function of NADPH-Cytochrome c reductase and NADPH-dependent mixed function amine oxidase of porcine liver microsomes. Arch. Biochem. Biophys., 145, 358
Coutts, R. T. and Beckett, A. H. (1977). Metabolic N-oxidation of primary and secondary aliphatic medicinal amines. Drug Metabol. Rev., 6, 51
Udenfriend, S., Clark, C. T., Axelrod, J. and Brodie, B. B. (1954). Ascorbic acid in aromatic hydroxylation. J. Biol. Chem., 208, 731
Rait, D. and Tannenbaum, S. R. (1980). Unpublished data.
Kosaka, H., Imaizumi, K., Imai, K. and Tyuma, I. (1979). Stoichiometry of the reaction of oxyhemoglobin with nitrite. Biochim. Biophys. Acta, 581, 184
Hewitt, E. J. (1975). Assimilatory nitrate-nitrite reduction. Ann. Rev. Plant Physiol., 26, 73
Hewitt, E. J. (1974). Aspects of trace element requirements in plants and micro-organisms: The metallo enzymes of nitrate and nitrite reduction. Plant Biochem., 11, 199
Beevers, L., Schrader, L. E., Flesher, D. and Hageman, R. H. (1965). Aspects of trace element requirements in plants and micro-organisms: The metallo enzymes of nitrate and nitrite reduction. Plant Physiol, 40, 691
MacGregor, C. H. and Schnaitman, C. A. (1972). Restoration of reduced nicotinamide adenine dinucleotide phosphate-nitrate reductase activity of a Neurospora mutant by extracts of various chlorate resistant mutants of E. coli. J. Bact., 112, 388
Villarreal-Moguel, E. I., Ibarra, V., Ruiz-Herrera, J. and Gitler, C. (1973). Resolution of the nitrate reductase complex from the membrane of E. coli. J. Bact., 113, 1264
Downey, R. J. (1972). Formation of NADPH nitrate reductase in Aspergillus nidulans. Am. Soc. Microbiol. Ann. Meet., Abst. No. P236, p. 175
Johnson, J. L., Hainline, B. E. and Rajagopalan, K. V. (1980). Characterization of the molybdenum cofactor of sulfite oxidase, xanthine oxidase and nitrate reduction. J. Biol Chem., 255, 1783
Solomonson, L. P. (1974). Regulation of nitrate reductase activity by NADH and cyanide. Biochim. Biophys. Acta, 334, 297
Herrera, T., Paneque, A., Maldonado, T. M., Barea, J. L. and Losada, M. (1972). Regulation by ammonia of nitrate reductase synthesis and activity in Chlamydomonas reinhardi. Biochem. Biophys. Res. Commun., 48, 996
Hucklesby, D. P. and Hewitt, E. J. (1970). Nitrite and hydroxylamine reduction in higher plants. Biochem. J., 119, 615
Prabhakararao, K. and Nicholas, D. J. D. (1970). The reduction of sulphite, nitrite and hydroxylamine by an enzyme from Baker’s yeast. Biochim. Biophys. Acta, 216, 122
Abou-Jaoude, A., Pascal, M. C. and Chippaux, M. (1979). Formate-nitrite reduction in E. coli K12. E.R. J. Biochem., 95, 315
Zumft, W. G. (1972). Ferredoxin: nitrite reduction in E. coli. Biochim. Biophys. Acta, 276, 363
Singh, J. (1973). Cytochrome oxidase from Pseudomonas aeruginosa. III. Reduction of hydroxylamine. Biochim. Biophys. Acta, 333, 28
Losada, M. (1973). Interconversion of nitrate and nitrite reductase of the assimilatory type. 3rd Int. Symp. Metab. Interconversion of Enzymes, pp. 257–270. Seattle, Washington
Cohen, B. S. and Weinhouse, S. (1971). Reduction of nitrate to nitrite in tissues of the rat. Abstract No. 179 162nd American Chemical Society Natl Meeting, Washington, DC
Rajagopalan, K. V., Fridovich, I. and Handler, P. (1962). Hepatic aldehyde oxidase. I. Purification and properties. J. Biochem. Chem., 237, 922
Krenitsky, T. A. (1978). Aldehyde oxidase and xanthine oxidase: functional and evolutionary relationships. Biochem. Pharmacol, 27, 2763
Kato, R., Iwasaki, K. and Noguchi, H. (1978). Reduction of tertiary amine N-oxides by cytochrome R-450. Molec. Pharmacol, 14, 654
Bernheim, M. L. C. and Hochstein, P. (1968). Reduction of hydroxylamine by rat liver mitochondria. Arch. Biochem. Biophys., 124, 436
Mitchell, H. H., Shonle, H. A. and Grindley, H. S. (1916). The origin of the nitrates in the urine. J. Biol Chem., 24, 461
Orii, Y. and Shimada, H. (1978). Nitrite metabolism by muscle in vitro. J. Biochem., 84, 1543
Walters, C. L. and Taylor, A. M. (1963). Nitrite metabolism by muscle in vitro. Biochim. Biophys. Acta, 86, 448
Nobbs, C. L., Watson, H. C. and Kendrew, J. C. (1966). Structure of deoxymyoglobin: A crystallographic study. Nature (London), 209, 339
Weiss, J. J. (1964). Nature of the iron-oxygen bond in oxyhaemoglobin. Nature (London), 202 83
Wittenberg, J. B., Wittenberg, B. A., Peisach, J. and Blumber, W. E. (1970). On the state of the iron and the nature of the ligand in oxyhemoglobin. Proc. Natl Acad. Sci., 67, 1846
Pauling, L. and Coryell, C. D. (1936). The magnetic properties and structure of hemoglobin, oxyhemoglobin and carbon-monoxyhemoglobin. Proc. Natl. Acad. Sci., 22, 210
Viale, R. O., Maggiora, G. M. and Ingraham, L. L. (1964). Molecular orbital evidence for Weiss’s oxyhemoglobin structure (Letter). Nature (London), 203, 183
Perutz, M. F. (1970). Stereochemistry of cooperative effects in haemoglobin. Nature (London), 228, 726
Perutz, M. F. (1978). Hemoglobin structure and respiratory transport. Sci. Am., 239 (6), 92
Bard, H. and Teasdale, F. (1979). Red cell oxygen affinity, hemoglobin type, 2,3-diphosphoglycerate, and pH as a function of fetal development. Pediatrics, 64, 483
Schwartz, J. M. and Jaffe, E. R. (1978). Hereditary methemoglobinemia with deficiency of NADH dehydrogenase. In Stanburg, J. et al (eds.) The Metabolic Basis of Inherited Disease, pp. 1452–1464.
Neill, J. M. (1925). Studies on the oxidation-reduction of hemoglobin and methemoglobin. J. Exp. Med., 41, 561
Conant, J. B. (1923). An electrochemical study of hemoglobin. J. Biol. Chem., 401
Peters, J. P. and Van Slyke, D. D. (1931). Quantitative Clinical Chemistry, Interpretation, pp. 631–632. ( London: Baillière, Tindall and Cox )
Paul, W. D. and Kemp, C. R. (1944). Methemoglobin: a normal constituent of blood. Proc. Soc. Exp. Biol. Med., 56, 55
VanSlyke, D. D., Hiller, A., Weisiger, J. R. and Cruz, W. O. (1946). Determination of carbon monoxide in blood and of total and active hemoglobin by carbon monoxide capacity: Inactive hemoglobin and methemoglobin contents of normal blood. J. Biochem., 166, 121
Scott, E. M. (1968). Congenital methemoglobinemia due to DPNH-diaphorase deficiency. In Beutler, E. (ed.) Hereditary Disorders of Erythrocyte Metabolism. ( New York: Grüne and Stratton )
Goldsmith, J. H., Rokaw, S. N. and Shearer, L. A. (1975). Distributions of percentage methaemoglobin in several population groups in California. Int., J. Epidemiol., 4, 207
Cox, W. W. and Wendel, W. G. (1942). The normal rate of reduction of methemoglobin in dogs. J. Biol. Chem., 143, 331
Francois (1844–1845) Cas de cyanose congeniale sans cause apparente. Bull. Acad. R. M. Belg., 4, 698
Slosse, A. and Wybauw, R. (1912). Un cas de methemoglobinemie idiopathique. Ann. Bull. Soc. R. Sci. Med. Nat. Bruxelles, 70, 206
Sievers, R. F. and Ryan, J. B. (1945). Congenital idiopathic methemoglobinemia: favorable response to ascorbic acid therapy. Arch. Intern. Med., 76, 299
Gibson, Q. H. (1943). The reduction of methaemoglobin by ascorbic acid. Biochem. J., 37, 615
Deeny, J., Murdock, E. T. and Rogan, J. J. (1943). Familial idiopathic methaemoglobinaemia with a note on the treatment of two cases with ascorbic acid. Br. Med. J., 1, 721
King, E. J., Gikhrest, M. and White, J. C. (1944). A case of methemoglobinemia. Biochem. J., 38
Scott, E. M. and Griffith, I. V. (1959). The enzymic defect of hereditary methemoglobinemia: Diaphorase. Biochim. Biophys. Acta, 34, 584
Scott, E. M. (1960). The relation of diaphorase of human erythrocytes to inheritance of methemoglobinemia. J. Clin. Invest., 39, 1176
Jaffe, E. R. (1963). The reduction of methemoglobin in erythrocytes of a patient with congenital methemoglobinemia, subjects with erythrocyte glucose-6-phosphate dehydrogenase deficiency and normal individuals. Blood, 21, 561
Ross, J. D. and Desforges, J. F. (1959). Reduction of methemoglobin by erythrocytes from cord blood. Pediatrics, 23, 718
Ross, J. D. (1963). Deficient activity of DPNH dependent methemoglobin diaphorase in cord blood erythrocytes. Blood, 21, 51
Bartos, H. R. and Desforges, J. F. (1966). Erythrocyte DPNH dependent diaphorase levels in infants. Pediatrics, 37, 991
Scott, E. M., Duncan, I. W. and Ekstrand, V. (1965). The reduced pyridine nucleotide dehydrogenases of human erythrocytes. J. Biol. Chem., 240, 481
Kanazawa, Y., Hattori, M, Kosaka, K. and Nakao, K. (1968). The relationship of NADH- dependent diaphorase activity and methemoglobin reduction in human erythrocytes. Clin. Chim. Acta, 19, 524
Petragnani, N., Nogueira, O. C. and Raw, I. (1959). Methaemoglobin reduction through cytochrome b5. Nature (London), 184, 1651
Hultquist, D. E. and Passon, P. G. (1971). Catalysis of methaemoglobin reduction by erythrocyte cytochrome b5 and cytochrome b5 reductase. Nature New Biol, 229, 252
Hultquist, D. E. (1978). Erythrocyte cytochrome b5; structure, role in methemoglobin reduction, and solubilization from endoplasmic reticulum. Prog. Clin. Biol. Res., 21, 199
Leroux, A., Torlinski, L. and Kaplan, J. C. (1977). Soluble and microsomal forms of NADH-cytochrome b5 reductase from human placenta: similarity with NADH-methemoglobin reductase from human erythrocytes. Biochim. Biophys. Acta, 481, 50
Abe, K. and Sugita, Y. (1979). Properties of cytochrome b5 and methemoglobin reduction in human erythrocytes. Eur. J. Biochem., 101, 423
Hultquist, D. E. (1978). Methemoglobin reduction system of erythrocytes. Methods Enzymol., 52, 463
Warburg, O. and Christian, W. (1931). Uber Aktivierung der Robisonschen Hexose-mono- phosphorsaure in roten Blutzellen und die Gewinnung aktivierender Fermentlosungen. Biochem. Z., 242, 206
Warburg, O. and Griese, A. (1935). Wasserstoffubertragendes Co ferment, seine Zusammensetzung und Wirkungsweise. Biochem. Z., 282, 157
Kiese, M. (1944). Die Reduktion des Hamoglobins. Biochem. Z., 316, 264
Huennekens, F. M., Caffrey, R. W., Basford, R. E. and Gabrio, B. W. (1957). Erythrocyte metabolism. IV. Isolation and properties of methemoglobin reductase. J. Biol Chem., 227, 261
Huennekens, F. M., Lin, L., Myers, H. A. P. and Gabrio, B. W. (1957). Erythrocyte metabolism. III. Oxidation of glucose. J. Biol. Chem., 227, 253
Sass, M. D., Caruso, C. J. and Farhangi, M. (1967). TPNH-methamoglobin reductase deficiency: A new red-cell enzyme defect. J. Lab. Clin. Med., 70, 760
Sass, M. D., Caruso, C. J. and Axelrod, D. R. (1969). Mechanism of the TPNH-linked reduction of methemoglobin by methylene blue. Clin. Chim. Acta, 24, 77
Tomoda, A., Takeshita, M. and Yoneyama, Y. (1978). Analysis of met-form hemoglobin in glucose-deleted human red cells. FEBS Lett., 88, 247
Mansouri, A. and Winterhalter, K. H. (1973). Nonequivalence of chains in hemoglobin oxidation. Biochemistry, 12, 4946
Isselbacher, K. J., Adams, R. D., Braunwald, E., Petersdorf, R. G. and Wilson, J. D. (1980). Harrison’s Principles of Internal Medicine, 9th ed., p. 1552. ( New York: McGraw-Hill )
Kaplan, J. C. and Chirouze, M. (1979). Therapy of recessive congenital methaemoglo- binaemia by oral riboflavin, (letter). Lancet, 2, 1043
Jaffe, E. R. and Neumann, G. (1964). A comparison of the effect of menadione, methylene blue and ascorbic acid on the reduction of methaemoglobin in vivo. Nature (London), 202, 607
Tarlov, A. R., Brewer, G. J., Carson, P. E. and Alving, A. S. (1962). Primaquine sensitivity. Glucose-6-phosphate dehydrogenase deficiency: an inborn error of metabolism of medical and biological significance. Arch. Intern. Med., 109, 209
Brewer, G. J., Tarlov, A. R., Kellermeyer, R. W. and Alving, A. S. (1962). The hemolytic effect of primaquine. XV. Role of methemoglobin. J. Lab. Clin. Med., 59, 905
Douglas, C. G., Haldane, J. S. and Haldane, J. B. S. (1912). The laws of combination of haemoglobin with carbon monoxide and oxygen. J. Physiol 44, 275
Darling, R. C. and Roughton, F. J. W. (1942). The effect of methemoglobin on the equilibrium between oxygen and hemoglobin. Am. J. Physiol, 137, 56
Brewer, G. J. (1971). Clinical implications of variation in erythrocyte oxygen affinity: A. Blood storage and B. Arteriosclerosis. In Astrup, P. and Rorth, M. (eds.) Oxygen Affinity of Hemoglobin and Red Cell Acid Base Status, pp. 629–645. ( New York: Academic Press )
Enoki, Y., Tokui, H. and Tyuma, I. (1969). Oxygen equilibria of partially oxidized hemoglobin. Respir. Physiol, 7, 300
Kiese, M. (1966). The biochemical production of ferrihemoglobin forming derivatives from aromatic amines, and mechanisms of ferrihemoglobin formation. Pharmacol Rev., 18, 1091
Smith, R. P. and Olson, M. V. (1973). Drug-induced methemoglobinemia. Semin. Hematol, 10, 253
Castro, C. E., Wade, R. S. and Belser, N. O. (1978). Conversion of oxyhemoglobin to methemoglobin by organic and inorganic reductants. Biochemistry, 17, 225
Wind, M. and Stern, A. (1977). Comparison of human adult and fetal hemoglobin: Aminophenol-induced methemoglobin formation. Experientia, 33, 1500
Gamgee, A. (1880). A Text-book of the Physiological Chemistry of the Animal Body. pp. 109–112. ( London: Macmillan and Co. )
Haldane, J., Makgill, R. H. and Mavrogordato, A. E. (1897). The action as poisons of nitrites and other physiologically related substances. J. Physiol, 21, 160
Greenberg, L. A., Lester, D. and Haggard, H. W. (1943). The reaction of hemoglobin with nitrite. J. Biol Chem., 151, 665
Meier, R. (1925). Studien uber Methamolgobinbildung. VII. Nitrit. Arch. Exp. Pathol Pharmakol, 110, 241
Harvey, J. W. and Kaneko, J. J. (1976). Oxidation of human and animal haemoglobins with ascorbate, acetylphenylhydrazine, nitrite, and hydrogen peroxide. Br. J. Haematol, 32, 193
Cohen, G., Martinez, M. and Hochstein, P. (1964). Generation of hydrogen peroxide during the reaction of nitrite with oxyhemoglobin. Biochemistry, 3, 901
Smith, R. P. (1970). Some features of the reaction between cobalt, nitrite and hemoglobin. Toxicol. Appl Pharmacol., 17, 634
Betke, K., Greinacher, I. and Tietze, O. (1956). Oxidation menschlicher und tierischer oxyhamoglobin durch natrium nitrit. Arch. Exp. Pathol. Pharmakol, 229, 220
Kiese, M. (1967), Reactions of N,N-dimethylamine-N-oxide with hemoglobin. Molec. Pharmacol., 3, 9
Rodkey, F. L. (1976). A mechanism for the conversion of oxyhemoglobin to methemoglobin by nitrite. Clin. Chem., 72, 1986
Mansouri, A. (1979). Oxidation of human hemoglobin by sodium nitrite—effect of beta-93 thiol groups. Biochem. Biophys. Res. Commun., 89, 441
Austin, J. H. and Drabkin, D. L. (1935). Spectrophotometry studies. III. Methemoglobin. J. Biol. Chem., 112, 67
Jung, F. and Remmer, H. (1949). Uber die Umsetzung zwischen Nitrit und Hamoglobin. Arch. Exp. Pathol. Pharmakol., 206, 459
Assendelft, O. W. V. and Ziljstra, W. G. (1965). The formation of hemiglobin using nitrites. Clin. Chim. Acta, 11, 571
Smith, R. P. (1967). The nitrite methemoglobin complex—its significance in methemoglobin analysis and its possible role in methemoglobinemia. Biochem. Pharmacol., 16, 1655
Gibson, Q. H., Parkhurst, L. G. and Gevaci, G. (1969). The reaction of methemoglobin with some ligands. J. Biol. Chem., 244, 4668
Uchida, H. and Klapper, M. H. (1970). Evidence for an irreversible reaction between nitrite and human methemoglobin. Biochim. Biophys. Acta, 221, 640
Smith, R. P. and Gosselin, R. E. (1966). On the mechanism of sulfide inactivation by methemoglobin. Toxicol Appl Pharmacol, 8, 159
Coryell, C. D., Pauling, L. and Dodson, R. W. (1939). The magnetic properties of intermediates in the reactions of hemoglobin. J. Phys. Chem., 43, 825
Imaizumi, K., Tyuma, I., Imai, K., Kosaka, H. and Ueda, Y. (1980). In vivo studies on methemoglobin formation by sodium nitrite. Int. Arch. Occup. Environ. Hlth, 45, 97
Chien, J. C. W. (1969). Reactions of nitric oxide with methemoglobin. J. Am. Chem. Soc., 91, 2156
Benesch, R., Benesch, R. E. and Yu, C. I. (1968). Reciprocal binding of oxygen and diphosphoglycerate by human hemoglobin. Proc. Natl Acad. Sci., 59, 526
Perutz, M. F., Ferscht, A. R., Simon, S. R. and Roberts, G. C. K. (1974). Influence of globin structure on the state of heme. II. Allosteric transitions in methemoglobin. Biochemistry, 13, 2174
Martin, H. and Huisman, T. H. J. (1963). Formation of ferri-haemoglobin of isolated haemoglobin types by sodium nitrite. Nature (London), 200, 898.
Tomoda, A., Matsukawa, S., Takeshita, M. and Yoneyama, Y. (1977). Effect of inositol hexaphosphate on hemoglobin oxidation by nitrite and ferricyanide. Biochem. Biophys. Res. Commun., 74, 1469
Smith, R. P., Alkaitis, A. A. and Shafer, P. R. (1967). Chemically induced methemoglobinemias in the mouse. Biochem. Pharmacol, 16, 317
Smith, R. P. and Layne, W. R. (1969). A comparison of the lethal effects of nitrite and hydroxylamine in the mouse. J. Pharmacol Exp. Therap., 165, 30
Bunn, H. F., Forget, B. G. and Ranney, H. M. (1977). Human Hemoglobins ( Philadelphia: W. B. Saunders )
Kravitz, H., Elegant, L. D., Kaiser, E. and Kagan, B. M. (1956). Methemoglobin values in premature and mature infants and children. Am. J. Dis. Child., 91, 1
Kunzer, W., Schuzz, A. and Schutz, E. (1956). Vergleichende Untersuchung der Spontanoxydation edes Blutfarbstoffes in Nabelschnur- und Erwachsenen-erythrocyten nach Glykolysehemmung. Acta Haematol, 16, 137
Bennecke and Hoffman (1906). First fatal case of bismuth subnitrate poisoning reported in the literature. Muench. Med. Wochenschr.
Boehme (1907). Report of fatal case of Bismuth Subnitrate poisoning. Arch. Exp. Pathol Pharmakol
Beck, E. G. (1909). Toxic effects from bismuth subnitrate. J. Am. Med. Assoc., 52, 14
Eusterman, G. B. and Keith, N. M. (1929). Transient methemoglobinemia following administration of ammonium nitrate. Med. Clin. North Am., 12, 1489
Roe, H. E. (1933). Methemoglobinemia following the administration of bismuth subnitrate: report of a fatal case. J. Am. Med. Assoc., 101, 352
Comly, H. H. (1945). Cyanosis in infants caused by nitrates in well water. J. Am. Med. Assoc., 129, 112
Lecks, H. L. (1950). Methemoglobinemia in infancy. Am. J. Dis. Child., 79, 117
Cornblath, M. and Hartmann, A. F. (1948). Methemoglobinemia in young infants. J. Pediatr., 33, 421
Marriott, M. W., Hartmann, A. F. and Senn, M. J. E. (1933). Observations on the nature and treatment of diarrhoea and the associated systemic disturbances. J. Pediatr., 3, 181
Robertson, H. E. and Riddell, W. A. (1949). Cyanosis of infants produced by high nitrate concentration in rural waters of Saskatchewan. Cañad. J. Pub. Hlth, 40, 72
Knotek, Z. and Schmidt, P. (1964). Pathogenesis, incidence and possibilities of preventing alimentary nitrate methemoglobinemia in infants. Pediatrics, 34, 78
Walton, G. (1951). Survey of literature relating to infant methemoglobinemia due to nitrate- contaminated water. Am. J. Pub. Hlth, 41, 986
Simon, C., Manzke, H., Kay, H. and Mrowetz, G. (1964). Uber Vorkommen, Pathogenese und Möglichkeiten zur Prophylaxe der durch Nitrit verursachten Methämoglobinämie. Z. Kinderheilkd., 91, 124
Shuval, H. I. and Gruener, N. (1972). Epidemiological and toxicological aspects of nitrates and nitrites in the environment. Am. J. Pub. Hlth, 62, 1045
Simon, C. (1966). Nitrite poisoning from spinach (letter). Lancet, 1, 872
Paneque, A., DelCampo, F. F., Ramirez, J. M. and Losada, M. (1965). Flavin nucleotide nitrate reductase from spinach. Biochim. Biophys. Acta, 109, 79
Schuphan, W. (1965). Der Nitrategehalt von Spinat (Spinacia oler aces L.) in Beziehung zur Methamoglobinanamie. Z. Ernaehrungsmss., 5, 207
Phillips, W. E. J. (1968). Changes in the nitrate and nitrite contents of fresh and processed spinach during storage. J. Agr. Food Chem., 16, 88
Phillips, W. E. J. (1969). Lack of nitrite accumulation in partially consumed jars of baby food. Canad. Inst. Food Tech. J., 2, 160
Phillips, W. E. J. (1971). Naturally occurring nitrate and nitrite in foods in relation to infant methaemoglobinaemia. Food Cosmet. Toxicol, 9, 219
Heisler, E. G., Siciliano, J., Krulick, S., Feinberg, J. and Schwartz, J. H. (1974). Changes in nitrate and nitrite content, and search for nitrosamines in storage-abused spinach and beets. Agrie. Food Chem., 22, 1029
Holscher, P. M. and Natzschka, J. (1964). Methamoglobinanamie bei jungen Säuglingen durch nitrithaltigen Spinat. Dtsch. Med. Wochenschr., 89, 1751
Sinious, A. and Wodsak, W. (1965). Die Spinatvergiftung des Säuglings. Dtsch. Med. Wochenschr., 90, 1856
Keating, J. P., Lell, M. E., Stauss, A. W., Zarkowsky, H. and Smith, G. E. (1973). Infantüe methemoglobinemia caused by carrot juice. N. Engl. J. Med., 288, 824
Orgeron, J. D., Martin, J. D., Caraway, C. T., Martine, R. M. and Hanser, G. H. (1957). Methemoglobinemia from eating meat with high nitrite content. Pub. Hlth Rep., 72, 189
Golba, J., Klecha, I., Kurowski, M. and Waluszkiewicz, H. (1977). Mass food poisoning with sodium nitrite. Pol. Tyg. Lek., 32, 1275
Greenberg, M., Birnkrant, W. G. and Schiftner, J. J. (1945). Outbreak of sodium nitrite poisoning. Am. J. Pub. Hlth, 35, 1217
Roueche, B. (1954). Eleven blue men and other narratives of Medical Detection. ( Boston: Little Brown )
Tepperman, J., Marquardt, R., Reifenstein, G. and Lozner, E. (1951). Methemoglobinemic cyanosis-report of an epidemic due to corning extract substituted for maple syrup. J. Am. Med. Assoc., 146, 923
Bakshi, S. P., Fahey, J. L. and Pierce, L. E. (1967). Sausage cyanosis-acquired methemoglobinemic nitrite poisoning. N. Engl. J. Med., 277, 1072
Hill, T. W. (1878). Poisoning from an overdose of sweet spirits of nitre, resembling a case of acute alcoholic poisoning. Lancet, 2, 766
Chilcote, R. R., Williams, B., Wolf, L. J. and Baenher, R. L. (1977). Sudden death in an infant from methemoglobinemia after administration of’sweet spirits of nitre’. Pediatrics, 59, 280
Naidu, S. R. and Venkatrao, P. (1936). Case of nitrite poisoning. Br. Med. J., 1, 1300
Naidu, S. R. and Venkatrao, P. (1945). The toxicology of nitrites. Calcutta Med. J., 42, 79
Huziter-Kramer, H. (1936). Sodium nitrite poisoning. Samml. Vergiftungsfaellen, 7, 15
McQuiston, T. A. C. (1936). Fatal poisoning by sodium nitrite. Lancet, 2, 1153
Padberg, L. E. and Martin, T. (1939). Three fatal cases of poisonings. J. Am. Med. Assoc., 113, 1733
Ruegg, H. (1935). Nitrite poisoning. Schweiz. Med. Wochenchschr., 16, 809
Wilson, L. G. (1976). Accidental sodium nitrite ingestion. Med. J. Aust., 1, 505
Sevier, J. N. and Berbatis, G. G. (1976). Accidental sodium nitrite ingestion. Med. J. Aust., 1, 847
Standefer, J. C., Jones, A. M., Street, E. and Inserra, R. (1979). Death associated with nitrite ingestion: report of a case. J. Forensic Sci., 24, 768
Harris, J. C., Rumack, B. H., Peterson, R. G. and McGuire, B. M. (1979). Methemoglobinemia resulting from absorption of nitrates. J. Am. Med. Assoc., 242, 2869
Henderson, W. R. and Raskin, N. H. (1972). ‘Hot-dog’ headache: individual susceptibility to nitrite. Lancet, 2, 1162
Sollman, T. (1957). A Manual of Pharmacology. 8th edn. ( Philadelphia: W. B. Saunders )
Zimmermann, F. E. (1977). Genetic effects of nitrous acid. Mutat. Res., 39, 127
Wittmann-Liebold, B. and Wittman, H. G. (1965). Localization of amino acid exchanges of nitrite mutants of tobacco mosaic virus. Z. Vererbungsl., 97, 305
Barnet, W. E. and DeBusk, A. G. (1960). Nitrous acid induced reverse mutation in Neurospora crassa. Genetics, 45, 973
Gutz, H. (1961). Nitrous acid induced mutations in the genetic fine structure of the ad-7 locus of Schizosaccharomyces pombe. Nature (London), 191, 1125
Kaudewitz, F. (1958). Production of bacterial mutants with nitrous acid. Nature (London), 183, 1829
Zahmenhof, S. (1958). Induction of mutations by deamination. Microb. Genet. Bull., 16, 33
Ishidate, M. and Odashima, S. (1977). Chromosome Tests with 134 compounds on Chinese hamster cells in vitro -a screening for chemical carcinogens. Mutat. Res., 48, 337
Kodama, F., Umeda, M. and Tsutsui, T. (1976). Mutagenic effect of sodium nitrite on cultured mouse cells. Mutat. Res., 40, 119
Utakoji, T. (1974). Chromosomal aberrations caused by sodium nitrite ( -2 ) in PHA cultures of human peripheral blood lymphocytes (meeting abstract). Gann Proceedings of the Japanese Cancer Assoc., 33rd Annual Meeting, p. 27, Sendai, Japan
Sauro, F., Friedman, L. and Green, S. (1973). Biochemical, mutagenic and pathological effects of nitrosamines in rats (meeting abstract). Toxicol Appl. Pharmacol, 25, 449
Knudsen, I. and Meyer, O. A. (1977). Mutagenicity studies on rats and mice given canned, heated nitrite-treated pork. Mutat. Res., 56, 177
Druckrey, H., Steinhoff, D., Beuthner, H., Schneider, H. and Klarner, P. (1963). Prufung von Nitrit auf chronisch toxische Wirkung an Ratten. Arzneim. Forsch., 13, 320
Van Logten, M. J., Den Tonkelaar, E. M., Kroes, R., Berkvens, J. M. and Van Esch, G. J. (1972). Long-term experiment with canned meat treated with sodium nitrite and glucono-ω-lactone in rats. Food Cosmet. Toxicol, 10, 475
Taylor, H. W. and Lijinsky, W. (1975). Tumor induction in rats by feeding heptamethyleneimine and nitrite in water. Cancer Res., 35, 812
Olsen, P. and Meyer, O. (1976). Carcinogenicity study on rats fed on canned heated nitrite- treated meat: preliminary communication. Proc. 2nd Intl. Symp. Nitrite Meat Prod., pp. 275–278.
Inai, K., Aoki, Y. and Tokuoka, S. (1979). Chronic toxicity of sodium nitrite in mice, with reference to its tumorigenicity. Gann, 70, 203
Sander, J. (1970). Induction of malignant tumors in rats by oral administration of N,N′-Dimethylurea and sodium nitrite. Arzneim. Forsch., 20, 418
Greenblatt, M., Mirvish, S. and So, B. (1971). Nitrosamine studies: Induction of lung adenomas by concurrent administration of sodium nitrite and secondary amines in Swiss mice. J. Natl Cancer Inst., 46, 1029
Scheunig, G., Horn, K. H. and Mehnert, W. H. (1979). Induction of tumors in Wistar-rats after oral application of amino pyrine and nitrite. Arch. Geschwulstforsch., 49, 220
Shank, R. C. and Newberne, P. M. (1976). Dose-response study of the carcinogenicity of dietary sodium nitrite and morpholine in rats and hamsters. Food Cosmet. Toxicol, 14, 1
Matsukura, N., Kawachi, T., Sasajima, K., Sano, T., Sugimura, T. and Ho, N. (1977). Induction of liver tumors in rats by sodium nitrite and methylguanidine. Z. Krebsforsch., 90, 87
Newberne, P. M. (1979). Nitrite promotes lymphoma incidence in rats. Science, 204, 1079
Lachance, P. A. (1978). Nitrites: The Newberne Report (letter). Science, 202, 576
Food and Drug Administration and U.S. Department of Agriculture. (1978). FDA’s and USD A* s Action Regarding Nitrite, August, 1978
Hartman, S. L. (1979). Case history of FDA actions on M.I.T. nitrite study. Congressional Record, September 12, 1979, p. H7787–7792
Expert Panel on Nitrites and Nitrates. (1978). Final Report on Nitrites and Nitrosamines. Report to the Secretary of the US Department of Agriculture, February, 1978
Council for Agricultural Science and Technology. (1978). Nitrite in meat curing: risks and benefits. Congressional Record, 124, 95th Congress, 2nd Session
Committee on Government Operations. (1972). Nineteenth Report. Regulation of food additives-nitrites and nitrates. Union Calendar No. 701, 92nd Congress, 2nd Session, House Report No. 92–1338 ( Washington, DC: US Govt. Printing Office )
Culliton, B. J. (1978). Nitrites—to ban or not to ban ? Br. Med. J., 2, 1613
Anonymous (1980). Plan to ban nitrites in foods dropped for now. Chem. Eng. News, p. 11. August 25, 1980
Taylor, J. M. and Morgenroth, V. H. (1979). Comparison of studies on saccharin and sodium nitrite. J. Assoc. Off. Anal. Chem., 62, 883
Globus, M. and Samuel, D. (1978). Effect of maternally administered sodium nitrite on hepatic erythropoiesis in fetal CD-I mice. Teratology, 18, 367
Sleight, S. D. and Atallah, O. A. (1968). Reproduction in the guinea pig as affected by chronic administration of potassium nitrate and potassium nitrite. Tox. Appl. Pharmacol., 12, 179
Sinha, D. P. and Sleight, S. D. (1971). Pathogenesis of abortion in acute nitrite toxicosis in guinea pigs. Toxicol. Appl. Pharmacol, 18, 340
Anderson, L. M., Giner-Sorolla, A., Ebeling, D. and Budinger, J. M. (1978). Effects of imipramine, nitrite and dimethylnitrosamine of reproduction in mice. Res. Commun. Pathol Pharmacol, 19, 311
Kawabata, T., Oshima, H., Uibu, J., Nakamura, M., Matsui, M. and Hamano, M. (1979). Occurrence, formation and precursors of N-nitroso compounds in Japanese diet. In Miller, E. C. et al. (eds.) Naturally Occurring Carcinogens-Mutagens and Modulators of Carcinogenesis, pp. 195–209. ( Baltimore: University Park Press )
Hill, M. J., Hawksworth, G. and Tattersall, G. (1973). Bacteria, nitrosamines and cancer of the stomach. Br. J. Cancer, 28, 562
Ville, J. and Mestrezat, W. (1907). Origine des nitrites contenus dans la salive; leur formation par reduction microbrenne des Nitrates éliminés par ce liquide. C. R. Soc. Biol., 73, 231
Keith, N. M., Whelan, M. and Bannick, E. G. (1930). The action and excretion of nitrates. Arch. Intern. Med., 46, 797
Goaz, P. W. and Biswell, H. A. (1961). Nitrate reduction in whole saliva. J. Dent. Res., 40, 355
Ishidate, M., Harada, M., Ishiwata, H., Nakamura, Y. and Tanimura, A. (1975). Studies on in vivo formation of nitrite. Proc. Japan Cancer Assoc., p. 66.33rd Annual Meeting, October, 1974
Harada, M., Ishiwata, H., Nakamura, Y., Tanimura, A. and Ishidate, M. (1975). Studies on in vivo formation of nitroso compounds. I. Changes of nitrite and nitrate concentration in human saliva after ingestion of salted Chinese cabbage. J. Food Hyg. Soc., 16, 11
Tannenbaum, S. R., Weisman, M. and Fett, D. (1976). The effect of nitrate intake on nitrite formation in human saliva. Food Cosmet. Toxicol, 14, 549
Spiegelhalder, B., Eisenbrand, G. and Preussmann, R. (1976). Influence of dietary nitrate on nitrite content of human saliva: possible relevance in vivo formation of N-nitroso compounds. Food Cosmet. Toxicol, 14, 545
Fett, D. R. (1977). The effect of diet on nitrate metabolism in man. (Masters Thesis. Massachusetts Institute of Technology)
Okabe, S. (1973). Fundamental studies on nitrite contents in human saliva. Hikone-Ronso, 162, 165
Hayashi, N., Watanabe, K., Ishiwata, H., Mizushiro, H., Tanimura, A. and Kurata, H. (1978). Fate of nitrate, and nitrite in saliva and blood of monkey administered orally sodium nitrate, solution, and microflora of oral cavity of the monkey. J. Food Hyg. Soc., Japan, 19, 391
Lowenfels, A. B., Tuyns, A. J., Walker, E. A. and Roussel, A. (1978). Nitrite studies in oesophageal cancer. Gut, 19, 199
Tannenbaum, S. R., Sinskey, A. J., Weisman, M. and Bishop, W. (1974). Nitrite in human saliva. Its possible relationship to nitrosamine formation. J. Natl. Cancer Inst., 53, 79
Ruddell, W. S. J., Blendis, L. M. and Walters, C. L. (1977). Nitrite and thiocyanate in the fasting and secreting stomach and in saliva. Gut, 18, 73
Klein, D., Gaconnet, N., Poullain, B. and Derby, G. (1978). Effet d’une charge en nitrate sur le nitrite salivaire et gastrique chez l’homme. Food Cosmet. Toxicol., 16, 111
Sander, J. and Seif, F. (1969). Bacterial reduction of nitrate in the human stomach as a cause for nitrosamine formation. Arzneim. Forsch., 19, 1091
Ruddell, W. S. J., Bone, E. S., Hill, M. J., Blendis, L. M. and Walters, C. L. (1976). Gastric- juice nitrite: A risk factor for cancer in the hypochlorhydric stomach? Lancet, 1, 1037
Ruddell, W. S. J., Bone, E. S., Hill, M. J. and Walters, C. L. (1978). Pathogenesis of gastric cancer in pernicious anaemia. Lancet, 1, 521
Jones, S. M., Davies, P. W. and Savage, A. (1978). Gastric-juice nitrite and gastric cancer [letter]. Lancet, 1, 1355
Schlag, P., Ulrich, H., Merkle, P., Bockler, R., Peter, M. and Herfarth, C. (1980). Are nitrite and N-nitroso compounds in gastric juice risk factors for carcinoma in the operated stomach? Lancet, 1, 727
Cruickshank, J. and Moyers, J. M. (1914). The presence and significance of nitrite in urine. Br. Med. J., 2, 712
Guignard, J. P. and Torrado, A. (1978). Nitrite indicator test strips for bacteria (letter). Lancet, 1, 47
Jogart, G. (1978). Screening for bacteriuria of school children by the nitrite reaction. Int. Urol. Nephrol., 10, 33
Kunin, C. M. and DeGroot, J. E. (1977). Sensitivity of a nitrite indicator strip method in detecting bacteriuria in preschool girls. Pediatrics, 60, 244
Scheifele, D. W. and Smith, A. L. (1978). Home-testing for recurrent bacteriuria using nitrite strips. Am. J. Dis. Child., 132, 46
Sinaniotis, C. A. (1978). Nitrite indicator strip test for bacteriuria [letter]. Lancet, 1, 776
Hill, M. J. and Hawksworth, G. (1972). Bacterial production of nitrosamines in vitro and in vivo. In Bogovski, P., Preussmann, R. and Walker, E. A. (eds.), N-Nitroso Compounds Analysis and Formation, IARC Scientific Publication No. 3, pp. 116–121. ( Lyon: IARC )
Brooks, J. B., Cherry, W. B., Thacker, L. and Alley, C. C. (1972). Analysis of gas-chromatography of amines and nitrosamines produced in vivo and in vitro by Proteus mirabilis. J. Infect. Dis., 126, 143
Hicks, R. M., Walters, C. L., Elsebai, I., El-Aasser, A. B., El-Merzabani, M. and Gough, T. A. (1977). Demonstration of nitrosamines in human urine: Preliminary observations on a possible etiology for bladder cancer in association with chronic urinary tract infections. Proc. R. Soc. Med., 70, 413
El-Merzabani, M. M., El-Aasser, A. A. and Zakhary, N. I. (1979). A study on the aetiological factors of Bilharzial bladder cancer in Egypt. 1. Nitrosamines and their precursors in urine. Eur. J. Cancer, 15, 287
Hill, M. J. and Hawksworth, G. (1974). Some studies on the production of nitrosamines in the urinary bladder and their subsequent effects. In Bogovski, P., Walker, E. A. and Davis, W. (eds.). N-Nitroso Compounds in the Environment, Int. Agency Res. Cancer Sci. Publ. 9, pp. 220–222. ( Lyon: IARC )
Burns, H. S. and Visscher, M. B. (1934). The influence of various anions of the lyotropic series upon the sodium and chloride content of fluid in the intestine. Am. J. Physiol., 110, 490
Hawksworth, G. M. and Hill, M. J. (1971). Bacteria and the N-nitrosation of secondary amines. Br. J. Cancer, 25, 520
Witter, J. P. and Balish, E. (1979). Distribution and metabolism of ingested NO3 and NO3 in germfree and conventional-flora rats. Appl Environ. Microbiol, 38, 861
Wang, C. F., Cassens, R. G. and Hoekstra, W. G. Metabolic fate of ingested 1,5-N-labeled nitrate and nitrite in the rat. J. Food Sci. (In press)
Saul, R. L., Kabir, S. H., Cohen, Z., Bruce, W. R. and Archer, M. C. A re-evaluation of nitrate and nitrite levels in the human intestine. (In preparation)
Tannenbaum, S. R., Fett, D., Young, V. R., Land, P. D. and Bruce, W. R. (1978). Nitrite and nitrate are formed by endogenous synthesis in the human intestine. Science, 200, 1487
Witter, J. P., Gatley, S. J. and Balish, E. (1979). Distribution of Nitrogen-13 from labeled nitrate (13NO3) in humans and rats. Science, 204, 411
Witter, J. P., Balish, E. and Gatley, S. J. (1979). Distribution of nitrogen-13 from labeled nitrate and nitrite in germfree and conventional-flora rats. Appl Environ. Microbiol., 38, 870
Fritsch, P. and DeSaint-Blanquat, G. (1976). Formation of nitrite from nitrates in the digestive tract. Ann. Nutr. Aliment., 30, 793
Friedman, M. A., Greene, E. J. and Epstein, S. S. (1972). Rapid gastric absorption of sodium nitrite in mice. J. Pharm. Sci., 61, 1492
Mirvish, S. S., Patil, K., Ghadirian, P. and Kommineni, V. R. C. (1975). Disappearance of nitrite from the rat stomach: contribution of emptying and other factors. J. Natl. Cancer Inst., 54, 869
Mysliwy, T. S., Wick, E. L., Archer, M. C., Shank, R. C. and Newberne, P. M. (1974). Formation of iV-nitrosopyrrolidine in a dog’s stomach. Br. J. Cancer, 30, 279
LeBar, J. and Sander, J. (1975). Carcinogenic N-Nitrosodimethylamine from the reaction of the analgesic amido pyrine and nitrite extracted from foodstuffs. Z. Krebsforsch., 84, 299
Gruener, N., Shuval, H. I., Behroozi, K., Cohen, S. and Shechter, H. (1973). Methemoglobinemia induced by transplacental passage of nitrites in rats. Bull. Environ. Contamin. Toxicol, 9, 44
Smith, P. L. R. and Walters, C. L. (1978). The transport of nitrite in the blood [proceedings]. Biochem. Soc. Trans., 6, 665
Kilgore, L., Almon, L. and Gieger, M. (1959). The effects of dietary nitrate on rabbits and rats. J. Nutr., 69, 39
Greene, I. and Hiatt, E. P. (1954). Behavior of the nitrate ion in the dog. Am. J. Physiol., 176, 463
Ruiz de Luzuriaga, K. F. (1980). Human nitrate metabolism: effect of dietary variables. ( Masters Thesis. Massachusetts Institute of Technology )
Tannenbaum, S. R., Green, L. C., Ruiz de Luzuriaga, K., Gordillo, G., Ullman, L. and Young, V. R. Endogenous carcinogenesis: nitrate, nitrite and N-nitroso compounds. In Carcinogenesis: Fundamental Mechanisms and Environmental Effects, Thirteenth Jerusalem Symposium, Jerusalem, April 28–May 2, 1980. (In press)
Cuello, C., Correa, P., Haenszel, W., Gordillo, G., Brown, C., Archer, M. and Tannenbaum, S. (1976). Gastric cancer in Colombia. I. Cancer risk and suspect environmental agents. J. Natl. Cancer Inst., 57, 1015
Ishiwata, H., Mizushiro, H., Tanimura, A. and Murata, T. (1978). Metabolic fate of precursors of N-nitroso compounds (III). Urinary excretion of nitrate in man. J. Food Hyg. Soc., Japan, 19, 318
Radomski, J. L., Palmiri, C. and Hearn, W. L. (1978). Concentrations of nitrate in normal human urine and the effect of nitrate ingestion. Tox. Appl. Pharmacol, 45, 63
Bartholomew, B., Caygill, C., Darbar, R. and Hill, M. J. (1979). Possible use of urinary nitrate as a measure of total nitrate intake. Proc. Nutr. Soc. (Engl.)
Maruyama, S., Shimizu, S. and Muramatsu, K. (1979). Dietary intake of nitrate and urinary excretion of nitrate in the population of several areas in Nagano prefecture. J. Food Hyg. Soc. Japan, 20, 276
Cahn, A. (1886). Die Magenverdauung im Chlorhunger. Z. Physiol Chem., 10, 522
Hiatt, E. P. (1940). Extreme hypochloremia in dogs induced by nitrate administration. Am. J, Physiol, 129, 597
Greene, I. and Hiatt, E. P. (1955). Renal excretion of nitrate and its effect on excretion of sodium and chloride. Am. J. Physiol, 180, 179
Berkman, P. M., deStrihou, C. Y., Needle, M. A., Gulyassy, P. F. and Schwartz, W. B. (1967). Factors which determine whether infusion of the sodium salt of an anion will induce metabolic alkalosis in dogs. Clin. Sci., 33, 517
Kahn, T., Bosch, J., Levitt, M. F. and Goldstein, M. H. (1975). Effect of sodium nitrate loading on electrolyte transport in the renal tubule. Am. J. Physiol., 229, 746
Weiner, M. W. (1978). Effects of chloride, nitrate and sulfate on ATPase of renal cortex and medulla. Proc. Soc. Exp. Biol. Med., 158, 370
Ganong, W. F. (1975). Review of Medical Physiology (Los Altos, California: Lange Medical Publications )
Wyngaarden, J. B., Wright, B. M. and Ways, P. (1952). The effect of certain anions upon the accumulation and retention of iodide by the thyroid gland. Endocrinology, 50, 537
Bloomfield, R. A., Weisch, C. W., Garner, G. B. and Muhrer, M. E. (1961). Effect of dietary nitrate on thyroid function. Science, 134, 1690
Brown-Grant, K. (1961). Extrathyroidal concentrating mechanisms. Physiol. Rev., 41, 189
Edwards, D. A., Fletcher, K. and Rowlands, E. N. (1954). Antagonism between perchlorate, iodide, thiocyanate and nitrate for secretion in human salvia. Lancet, 1, 498
Fletcher, K., Honour, A. J. and Rowlands, E. N. (1956). Studies on the concentration of radioiodide and thiocyanate in slices of the salivary gland. Biochem. J., 63, 194
Burgen, A. S. V. and Emmelin, N. E. (1961). Physiology of the Salivary Glands. ( Baltimore: Williams and Wilkins )
Cohen, B. and Myant, N. B. (1959). Concentration of salivary iodide: A comparative study. J. Physiol, 145, 595
Honour, A. J., Myant, N. B. and Rowlands, E. N. (1952). Secretion of radioiodine in digestive juices and milk in man. Clin. Sci., 11, 447
Brown-Grant, K. (1957). The iodide concentrating mechanism of the mammary gland. J. Physiol., 135, 644
Donahoe, W. E. (1949). Cyanosis in infants with nitrates in drinking water as cause. Pediatrics, 3, 308
Bloomfield, R. A., Hersey, J. R., Weisch, C. W., Garner, G. B. and Muhrer, M. E. (1962). Gastric concentration of nitrate in rats. (Meeting Abstract) J. Animal Sci., 21, 1019
Whelan, M. (1935). The nitrate content of animal tissues, and the fate of ingested nitrate. Biochem. J., 29, 782
Kurzer, M. and Calloway, D. H. (1979). Endogenous nitrate production in humans (Meeting Abstract), Fed. Proc., 38, 607
Green, L. C., Tannenbaum, S. R. and Goldman, P. (1981). Nitrate synthesis in the germfree and conventional rat. Science, 212, 56
Zaldivar, R. and Robinson, H. (1973). Epidemiological investigation on stomach cancer mortality in Chileans: association with nitrate fertilizer. Z. Krebsforsch., 80, 289
Doll, R. (1956). Environmental factors in the aetiology of cancer of the stomach. Gastroenterologia, 86, 320
Boyd, J., Langman, M. and Doll, R. (1964). The epidemiology of gastrointestinal cancer with special reference to causation. Gut, 5, 196
Dungal, N. (1961). The special problem of stomach cancer in Iceland. J. Am. Med. Assoc., 178, 789
Haenszel, W., Kurihara, M., Locke, F. B., Shimuzu, K. and Mitsuo, S. (1976). Stomach cancer in Japan. J. Natl Cancer Inst., 56, 265
Tempia, E., Health effects of water quality: a case study (personal communication)
Bogovski, P., Walker, E. A., Castegnaro, M. and Pignatelli, B. (1975). Some evidence of the presence of traces of nitrosamines in cider distillates. In N-Nitroso Compounds in the Environment, IARC Sci. Pub. No. 9, pp. 192–196. ( Lyon: IARC )
Fong, L. Y. Y. and Newberne, P. M. (1978). Nitrosobenzylmethylamine, zinc deficiency and oesophageal cancer. In Environmental Aspects of N-Nitroso Compounds, IARC Sci. Pub. No. 19, pp. 503–513. ( Lyon, France: IARC )
Song, Puju (1980). Personal communication
Haenszel, W., Correa, P., Cuello, C., Guzman, N., Burbano, L. C., Lores, H. and Munoz, J. (1976). Gastric cancer in Colombia. II. Case-control epidemiologic study of precursor lesions. J. Natl. Cancer Inst., 57, 1021
Correa, P., Cuello, C., Duque, E., Burbano, L. C., Garcia, F. T., Oscar, B., Brown, C. and Haenszel, W. (1976). Gastric cancer in Colombia. III. Natural history of precursor lesions. J. Natl Cancer Inst., 57, 1027
Correa, P., Cuello, C., Gordillo, G., Zarama, G., Lopez, J., Haenszel, W. and Tannenbaum, S. The gastric microenvironment in populations at high gastric cancer risk. JNCI Monographs on Cancer, in press
Tannenbaum, S. R. and Moran, D. (1980). Epidemiological studies of nitrate, nitrite and gastric cancer. In Proc. of Conference on Safety Evaluation of Nitrosatable Drugs and Chemicals, January 24 /25, London. ( In press )
Rifkind, R. A., Bank, A., Marks, P. A. and Nossel, H. L. (1976). Fundamentals of Hematology. ( Chicago: Year Book Medical Publishers )
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1982 MTP Press Limited
About this chapter
Cite this chapter
Green, L.C., Ralt, D., Tannenbaum, S.R. (1982). Nitrate, nitrite and N-nitroso compounds: biochemistry, metabolism, toxicity and carcinogenicity. In: Neuberger, A., Jukes, T.H. (eds) Human Nutrition. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-6258-6_4
Download citation
DOI: https://doi.org/10.1007/978-94-011-6258-6_4
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-011-6260-9
Online ISBN: 978-94-011-6258-6
eBook Packages: Springer Book Archive