Abstract
The dialkyl nitrosamines, of which dimethylnitrosamine and diethylnitrosamine are good examples, belong to the larger class of N-nitroso compounds, many of which are potent carcinogens in a large variety of animal species. In 1954 Barnes and Magee (1) demonstrated that dimethylnitrosamine was acutely hepatotoxic to laboratory animals. Subsequently, in 1956 they showed (2) that dimethylnitrosamine fed to rats produced a very high incidence of malignant liver tumor. These studies provided the impetus for extensive research on a whole range of nitroso compounds including their carcinogenity, pharmacology, chemistry, biochemistry, and mutagenic potential. The prodigious amount of literature that has accumulated in these different areas has been summarized in a number of excellent reviews (3–15).
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References
Barnes, J. M., and Magee, P. N. Brit. J. Ind. Med. 11: 167–174 (1954).
Magee, P. N., and Barnes, J. M. Brit. J. Cancer 114–122 (1956).
Bogovski, P., Preussmann, R., and Walker, E. A. N-Nitroso compounds: Analysis and Formation. International Agency for Research on Cancer, IARC Scientific Publ. 9, Lyon, 1974.
Druckrey, H., Preussmann, R., Ivanovic, S., et al. Z. Krebsforsch. 69: 103–201 (1967).
Heidelberger, C. Ann. Rev. Biochem. 44: 79–121 (1975).
Lijinsky, W. In: Chemical Mutagens: Principles and Methods for Their Detection, Vol. 4, A. Hollaender, Ed. Plenum Press, New York, 1976, pp. 193–215.
Lijinsky, W., and Singer, G. M. In: N-Nitroso Compounds in the Environment, P. Bogovski and E. A. Walker, Eds., IARC Scientific Publ. No. 9, Lyon, 1974, pp. 111–000.
Magee, P. N. In: In Vitro Metabolic Activation in Mutagenesis Testing, F. J. de Serres et al., Eds. North-Holland Publishers, Amsterdam, 1976, pp. 213–216.
Magee, P. N., and Barnes, J. M. Adv. Cancer Res. 10: 163–246 (1967).
Mirvish, S. S. In: Topics in Chemical Carcinogenesis, W. Nakahara et al., Eds., Univ. Tokyo Press, Tokyo, 1972, pp. 279–295.
Mirvish, S. S. J. Toxicol. Environ. Health 2: 1267–1277 (1977).
Montesano, R., and Bartsch, H. Mutat. Res. 32: 179–228 (1976).
Neale, S. Mutat. Res. 32: 229–266 (1976).
Singer, B. Trends Biochem. Sci. 2: 180–183 (1977).
Singer, B. J. Toxicol. Environ. Health 2: 1279–1295 (1977).
Druckrey, H., Steinhoff, D. et al. Arzneimittelforsch. 13: 320–323 (1963).
Lijinksy, W., Conrad, E., and Van de Bogart, R. Nature 239: 165–176 (1972).
Lijinsky, W., Keefer, L., Conrad, E., and Van de Bogart, R. J. Natl. Cancer Inst. 49: 1239–1249 (1972).
Magee, P. N., Montesano, R., and Preussmann, R. In: Chemical Carcinogens, C. Searle, Ed. American Chemical Society Monograph 173, Washington, D.C., 1976.
Lijinsky, W., and Epstein, S. Nature 225: 21–23 (1970).
IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man, Vol. 1, IARC, Lyon, 1972.
Montesano, R., and Magee, P. N. In: Chemical Carcinogenesis Assays, R. Montesano and L. Tomatis, Eds., IARC Scientific Publ. 10, Lyon, 1974, pp. 39–56.
Knecht, M. Z. Krebsforsch. 63:. 293–296 (1967).
Heath, D. F. Biochem. J. 85: 72–91 (1962).
Swann, P. F., and Magee, P. N. Biochem. J. 110: 39–47 (1968).
Swann, P. F., and Magee, P. N. Biochem. J. 125: 841–847 (1971).
Magee, P. N., and Vandekar, M. Biochem. J. 70: 600–605 (1958).
Montesano, R., and Magee, P. N. Nature 228: 173 (1970).
Brouwers, J. A. J., and Emmelot, P. Exptl. Cell Res. 19: 467 (1960).
Wilkinson, C. F., and Brattsen, L. B. Drug Metab. Rev. 1 (2): 153–228 (1972).
Baars, A. J., Zijlstra, J. A., Vogel, E., and Breimer, D. Mutat. Res. 44: 257–268 (1977).
Callen, D. F., and Philpot, R. M. Mutat. Res. 45: 309–324 (1977).
Magee, P. N., and Farber, E. Biochem. J. 83: 114–124 (1962).
Lijinsky, W., Loo, J., and Ross, A. E. Nature 218: 1174–1175 (1968).
Ross, A. E., Keefer, L. K., and Lijinsky, W. J. Natl. Cancer Inst. 47: 789–795 (1971).
Druckrey, H., Schildbach, A., Schmähl, D. et al. Arzneimettelforsch. K3: 841 (1963).
Krüger, F. W. Z. Krebsforsch. 19: 90–97 (1973).
Blattman, L., and Pressmann, R. Z. Krebsforsch. 79: 3–5 (1973).
Okada, M., and Suzuki, E. Gann 63: 391–392 (1972).
Druckrey, H. Chemische Struktur und Reaktionsmechanismen Kreserzeugender Substanzen. Umsch. Wiss. Tech., 1972, p. 94.
Lawley, P. D., and Thatcher, C. J. Biochem. J. 116: 693–707 (1970).
Lawley, P. D. Mutat. Res. 23: 283–295 (1974).
Goth, R., and Rajewsky, M. F. Z. Krebsforsch. 82: 37–64 (1974).
Nicoll, J. W., Swann, P. F., and Pegg, A. E. Nature 254: 261–262 (1975).
Goth, R., and Rajewsky, M. F. Proc. Natl. Acad. Sci. (U.S.A.) TU 639–643 (1974).
Kleihues, P., and Margison, G. P. J. Nat. Cancer Inst. 53: 1839–1841 (1974).
Margison, G. P., and Kleihues, P. Biochem. J. 148: 521–525 (1975).
Gerchman, L. L., and Ludlum, D. B. Biochem. Biophys. Acta 308: 310–316 (1973).
Lake, B. G., Minski, M. J. et al. Life Sci. 17: 1599–1606 (1976).
Roller, P. P., Shimp, D. R., and Keefer, L. K. Tetrahedron Letters 1975: 2065.
Wiessler, m. Angew. Chem. 86: 817 (1974).
Rice, J. M., Joshi, S. R. et al. Proc. Am. Assoc. Cancer Res. 16: 32 (1975).
Wiessler, M., and Schmaehl, D. Z. Krebsforsch. Klin. Onkol. 85: 47 (1976).
Magee, P. N. et al. Unpublished work.
Mailing, H. V. Mutat. Res. 3: 537–540 (1966).
Gabridge, M. G., and Legator, M. S. Proc. Soc. Exptl. Biol. Med. 130: 831–834 (1969).
Mohn, G., Ellenberger, J., and McGregor, D. Mutat. Res. 25: 187–196 (1974).
Mohn, G., Ellenberger, J., et al. Mutat. Res. 29: 221–233 (1975).
Nakajima, T., and Wahara, S. Mutat. Res. 18: 121–127 (1973).
Nakajima, T., Akira, T., and Tojyo, K. I. Mutat. Res. 26: 361–366 (1974).
Green, M. H. L. et al. Chem. Biol. Interact. 11: 63–65 (1975).
R. Osenkranz, H. S. In preparation.
Read, J. Mutat. Res. 33.: 107–112 (1975).
Longnecker, D. S., Curphey, T. J., Susan, J. T., et al. Cancer Res. 34: 1658–1663 (1974).
Fluck, E. R., Poirier, L. A., and Ruelius, H. W. Chem. Biol. Interact. 15: 219–231 (1976).
Natarajan, A. T. Mutat. Res. 46: 54 (1977).
Slater, E. E., Anderson, M. D., and Rosenkranz, H. S. Cancer Res. 31: 970–973 (1971).
Popper, H., Czygan, P. et al. Proc. Soc. Exptl. Biol. Med. 142: 727–729 (1973).
Kada, T., Tutikawa, K., and Sadaie, Y. Mutat. Res. 165–174 (1982).
Sadaie, Y., and Kada, T. J. Bacteriol. 125: 489–500 (1976).
Mailing, H. V. Mutat. Res. 13: 425–429 (1971).
Mailing, H. V. Mutat. Res. 26: 465–472 (1974).
Bartsch, H., Malaville, C., and Montesano, R. Cancer Res. 35: 644–651 (1975).
Gletten, F., Weekes, U., and Brusick, D. Mutat. Res. 28: 113–122 (1975).
Weekes, U., and Brusick, D. Mutat. Res. 31: 175–183 (1975).
Frantz, C. N., and Mailing, H. V. Cancer Res. 2307–2314 (1975).
Ames, B. Unpublished results.
Guttenplan, J. B., Huetterer, F., and Garro, A. J. Mutat. Res. 35: 415–422 (1976).
Bartsch, H., Malaville, C., and Montesano, R. Chem. Biol. Interact. 10: 377–382 (1975).
Frantz, C. N., and Mailing, N. V. Mutat. Res. 31: 365–380 (1975).
Mailing, H. V., and Frantz, C. N. Environ. Health Perspect. 6: 71–82 (1973).
Sugimura, T., Yahagi, T., et al. In: Screening tests in Chemical Carcinogenesis, R. Montesano, H. Bartsch, and L. Tomatis, Eds., IARC, Lyon, 1976.
Sugimura, T., Yahagi, T., et al. In: Screening tests in Chemical Carcinogenesis, R. Montesano, H. Bartsch, and L. Tomatis, Eds., IARC, Lyon, 1976.
Bartsch, H., Camus, A. et al. Mutat. Res. 37: 149–162 (1976).
Marquardt, H., Zimmermann, F. H., and Schwaier, R. Z. Vererbungsl. 95: 82–96 (1964).
Meyer, V. W. Mol. Gen. Genet. 112: 289–294 (1971).
Brusick, D., and Mayer, V. W. Environ. Health Perspect. 6: 83–96 (1973).
Mayer, V. W. Genetics 74: 433–442 (1973).
Brusick, D., and Andrews, H. Mutat. Res. 26: 491–500 (1974).
Mailing, H. V. Mutat. Res. 3: 537–540 (1966).
Ong, T. M., and Mailing, H. V. Mutat. Res. 31: 195–196 (1975).
Mohn, G., and Ellenberger, J. Mutat. Res. 19: 257–260 (1973).
Mazue, G., Vindel, J. A. et al. Arzenium Fosch. 24: 1422–1425 (1974).
Muenzer, R., and Renner, H. W. Int. J. Rad. Biol. 27: 371–375 (1975).
Propping, P., and Buselmaier, W. Arch. Toxikol. 28: 129–134 (1971).
Braun, R., and Schöneich, J. Unpublished results.
Couch, D. B., and Friedman, M. A. Mutat. Res. 26: 371–376 (1974).
Couch, D. B., and Friedman, M. A. Mutat. Res. 38: 89–96 (1976).
Zeiger, E. Dissert. Abstr. Int. B 34: 2108 (1973).
Propping, P., Röhrborn, G., and Buselmaier, W. Mol. Gen. Genet. 117: 197–209 (1972).
Fahrig, R. Mutat. Res. 21: 30 (1973).
Fahrig, R. Mutat. Res. 2(3: 29–36 (1974).
Fahrig, R. Mutat. Res. 31: 381–394 (1975).
Fumero, S., Mondino, A. et al. Paper presented at 2nd Int. Conf. Environ. Mutagens, Edinburgh, July 11–15, 1977.
Capizzi, R. L., Smith, W. J. et al. Mutat. Res. 21: 6 (1973).
Capizzi, R. L., Smith, W. J. et al. Mutat. Res. 21: 6 (1973).
Braun, R., and Schoeneich, J. Biol. Zentralbl. 94: 661–669 (1975).
Fahmy, O. J., and Fahmy, M. J. Chem. Biol. Interact. 11: 395–412 (1975).
Fahmy, O. J., and Fahmy, M. J. Cancer Res. 35: 3780–3785 (1975).
Ondrej, M. Folia Biol. (Prague) 15: 17–25 (1969).
Pasternak, L. Arzneimittelforsch. 802–804 (1964).
Vogel, E. Unpublished results.
Fahmy, O. G., and Fahmy, M. J. Mutat. Res. 6: 139–154 (1968).
Fahmy, O. J., Fahmy, M. J., et al. Mutat. Res. 3: 201–217 (1966).
Pasternak, L. Acta Biol. Med. Ger. 10: 436–438 (1963).
Pasternak, L. Arzneimittelforsch. L4: 802–804 (1964).
Vogel, E., and Leigh, B. Mutat. Res. 29: 383–396 (1975).
Vogel, E. In: The Origins of Human Cancer, Cold Spring Harbor Symp. Quant. Biol., to be published.
Russell, W. L. Unpublished data.
Dawson, G. W. P. Unpublished data.
Fahrig, R. Arch. Toxicol. 38: 87–98 (1977).
Russell, L. B. Arch. Toxicol. 38: 75–85 (1977).
Epstein, S., and Arnold, E., et al. Toxicol. Appl. Pharmacol. 23: 288–325 (1972).
Frantz, C. N., and Mailing, H. V. J. Toxicol. Environ. Health 2: 179–187 (1976).
Clive, D. Unpublished results.
Knaap, A. G. A. C. Unpublished results.
Abbondandolo, A., Bonatti, S., et al. Mutat. Res., in press.
Lilly, L. J., Bahner, B., and Magee, P. N. Nature 258: 611–612 (1975).
Bimboes, D., and Greim, H. Mutat. Res. 35: 155–160 (1976).
Brooks, A. L., and Grogger, V. Mutat. Res. 21 214 (1973).
Natarajan, A. T., Tates, A. D., et al. Mutat. Res. 37: 83–90 (1976).
Takayama, S., Hitachi, M., and Yamada, K. Gann Monographs on Cancer Res. 17: 343–354 (1975).
Zbar, B., Wepsic, H. T. et al. J. Natl. Cancer Inst. 43: 821–832 (1969).
Natarajan, A. T., van Buul, P. P., and Raposa, T. Paper presented at the Symposium on Actions of Physical and Chemical Mutagens on the Somatic Chromosomes of Man, Edinburgh, July 7 and 8, 1977.
Bauknecht, T., Vogel, W. et al. Hum. Genetics 35: 299–307 (1977).
Bauknecht, T., Vogel, W. et al. Hum. Genetics 35: 299–307 (1977).
Wild, D. Mutat. Res. 38: 105 (1976).
Lieberman, M. W., Baney, R. N. et al. Cancer Res. 31 1297–1306 (1971).
Laishes, B. A., and Stich, H. F. Biochem. Biophys. Res. Commun. 52: 827–833 (1973).
Stich, H. F., and Kieser, D. Proc. Soc. Exptl. Biol. Med. 145: 1339–1342 (1974).
Sega, G. A. Unpublished results.
Kihlman, B. A. Rad. Botany 1 35–41 (1961).
Kihlman, B. A. Rad. Botany: 43–50 (1961).
Arenaz, P. M. S. Thesis, Univ. Nevada, 1976, 102 pp.
Gichner, T. Unpublished results.
Veleminsky, J., and Gichner, T. Mutat. Res. 12: 65–70 (1971).
Veleminsky, J., and Gichner, T. Mutat. Res. 5: 429–431 (1968).
Mailing, H. V., and de Serres, F. J. Cancer Res. 32: 1273–1277 (1972).
Neubert, D. In: Progress in Genetic Toxicology, D. Scott et al., Eds., Elsevier/North-Holland, Amsterdam, 1977, pp. 95–115.
San, R. H. C., and Stich, H. F. Int. J. Cancer 16: 284–291 (1975).
Ichinotsubo, D., Mower, H. F., et al. Mutat. Res. 46: 53–62 (1977).
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Sankaranarayanan, K. (1981). Comparative Mutagenicity of Dimethylnitrosamine and Diethylnitrosamine. In: De Serres, F.J., Shelby, M.D. (eds) Comparative Chemical Mutagenesis. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-3409-5_27
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