The determination of N- nitrosamines in food
Main Article Content
Keywords
analytical methods, contamitants, food safety, nitrosamines
Abstract
Introduction N-nitrosamines are formed in food as a result of natural chemical interactions, but mainly through food processing activity. Most are potent carcinogens and their determination is therefore of considerable importance. They exist in various chemical forms and have been measured by colorimetric and spectroscopic methods following gas or liquid chromatography or as a total N-nitroso group by measurement of chemically released nitric oxide. Objectives To provide an overview of the available methods for the analysis of N-nitrosamines in food that includes recently developments. Methods The literature was reviewed from the discovery of the N-nitrosamine problem and the introduction on the N nitroso-specific detector. Results The evaluation shows that analytical detection methods for volatile N-nitrosamines in food have changed little since the introduction on the N-nitroso-specific detector and that research into the occurrence and formation of both non-volatile N-nitrosamines and the apparent total N-nitroso content (ATNC) have declined. Methods for measuring the apparent total N-nitroso content have not been improved significantly in recent years. Conclusion Modern sample extraction techniques and mass spectrometric
methods for the volatile N-nitrosamines have been applied more extensively to water analysis and offer a good opportunity to improve the determination of these carcinogens in food and make the analysis more widely available. Developments in liquid chromatography-mass spectrometry should provide an avenue for renewed interest in non-volatile N-nitrosamines, and could help with the identification of novel compounds whose presence is suggested by the high apparent total N-nitroso content of some foods.
References
Althorpe J., Goddard D.A., Sissons D.J., Telling G.M. (1970) The gas chromatographic determination of nitrosamines at the picogram level by conversion to their corresponding nitramines. Journal of Chromatography, 53, 371–373.
Andrade R., Reyes F.G.R., Rath S. (2005) A method for the determination of volatile N–nitrosamines in food by HS–SPME–GC–TEA. Food Chemistry,91, 173–179.
AOAC (2004) Official Methods of Analysis of the Association of Official Analytical Chemists, 19th Edition. Association of Official Analytical Chemists, USA.
Bartsch H., Spiegelhalder B. (1996) Environmental exposure to N-nitroso compounds (NNOC) and precursors: an overview. European Journal of Cancer Prevention,5, 11–17.
Baxter E.D., Slaiding I.R., Travers V. (2007) Current incidence of N-nitrosodimethylamine in beers worldwide. Food Additives and Contaminants, 24, 807–811.
Bellec G., Cauvin J.M., Salaun M.C., LeCalve K., Dreano Y., Gouerou H., Menez J.F., Berthou F. (1996) Analysis of N–nitrosamines by high-performance liquid chromatography with post–column photohydrolysis and colorimetric detection. Journal of Chromatography A,727, 83–92.
Biaudet H., Mavelle T., Debry G. (1994) Mean daily intake of N-nitrosodimethylamine from foods and beverages in France in1987–1992. Food Chemistry and Toxicology,32, 417–421.
Borwitzky H. (1986) Some improvements in the determination of volatile nitrosamines by fused silica capillary-GC in combination with a thermal energy analyzer. Chromatographia, 22, 65–72.
Bouchikhi B., Mavelle T., Debry G. (1989) Precautions to be taken in the analysis of total N-nitroso compounds. Food Additives and Contaminants, 6, 209–217.
Budeveska B.O., Rizov N.A., Gheoghiev G.K. (1986) Photolytic chemiluminescence detector for gas chromatographic analysis of N-nitroso compounds. Journal of Chromatography, 351,501–505.
Cardenes L., Ayala J.H., Gonzalez V., Afonso A.M. (2002a) Fastmicrowave–assisted dansylation of N-nitrosamines – Analysisby high-performance liquid chromatography with fluorescence detection. Journal of Chromatography A,946,133–140.
Cardenes L., Ayala J.H., Gonzalez V., Afonso A.M. (2002b)Determination of N-nitrosodimethylamine by HPLC, with fluorescence detection. A survey of N-nitrosodimethylaminein commercial beers. Journal of Liquid Chromatography andRelated Technologies,25, 977–984.
Castegnaro M., Massey R.C., Walters C.L. (1987) The collaborative evaluation of a procedure for the determination of N-nitroso compounds as a group. Food Additives and Contaminants, 4, 37–43.
Castegnaro M., Webb K.S. (1983) Detection techniques –Introduction. In: Environmental carcinogens – selected methods of analysis.6.N-nitroso compounds, Vol. 45 eds Preussman R, O’Neil L, Eisenbrand G, Spiegelhalder B, Bartsch B. pp.439–447, International Agency for Research on Cancer, Lyon, France.
Challis B.C., Colling J., Cromie D.D.O., Guthrie W.G., PollockJ.R.A., Taylor P., Telling G.M., Wallace L. (1995) A screening procedure for total N-nitroso contaminants in personal care products: results of collaborative studies undertaken by a CTPA Working Group. International Journal of Cosmetic Science,17, 219–231.
Choi J., Valentine R.L. (2002) Formation of N-nitrosodimethylamine (NDMA) from reaction of monochloroamine: a new disinfection by-product. Water Research, 36, 817–824.
Conboy J.J., Hotchkiss J.H. (1989) Photolytic interface for high–performance liquid-chromatography chemiluminescence detection of non-volatile N-nitrosocompounds. Analyst, 114, 155–159.
Crosby N.T. (1976) Nitrosamines in foodstuffs. Residue Reviews, 64, 77–135.
Crosby N.T, Sawyer R. (1976)N-nitrosamines: a review of chemical and biological properties and their estimation in foodstuffs. Advances in Food Research,22, 1–71.
Cutaia A.J. (1982) Malt beverages and brewing materials: screening and confirmatory methods for nitrosamines in beer. Journal of the Association of Official Analytical Chemists, 65,584–587.
Eisenbrand G., Arch M., Brunnemann K.D., Fine D.H., HechtS.S., Hoffmann D., Krull J., Webb K.S. (1983) Problems of contamination and artifact formation in nitrosamine sampling and analysis. In: N-Nitroso Compounds, IARC Scientific Publication No. 45, Vol. 6eds Preussmann R., O’Neill I.K., Eisenbr and G., Spiegelhalder B., Bartsch H. pp. 25–34, International Agency for Research on Cancer, Lyon, France.
Eisenbrand G., Janzowski C., Preussmann R. (1976) Gas chromatographic determination of nitrosamino acids by trimethylsilylation and single-ion monitoring in a gas chromatography-mass spectrometry system. In: Environmental N-Nitroso Compounds: Analysis and Formation, IARC Scientific Publication No. 14eds Walker E.A., Bogovski P., Griciute L. pp. 21–26, International Agency for Research on Cancer, Lyon, France.
Ender F., Havre G., Helgebostad A., Koppang N., Masden R., CehL. (1964) Isolation and identification of a hepatotoxic factor in herring meat produced from sodium nitrite preserved herring. Naturwissenschaften, 51, 637–638.
EPA (1997) US Environmental Protection Agency, N-Nitrosodimethylamine, CASRN 62–75–9, Integrated Risk Information System (IRIS) Substance File, 1993. Available at http://www.epa.gov/iris/subst/0045.htm
EPA (2004) Method 521: Determination of nitrosamines in drinking water by solid phase extraction and capillary column gas chromatography with large volume injection and chemical ionization tandem mass spectrometry (MS/MS), Ver.1.0, EPA Document # EPA/600/R–05/054. Available at http://www.epa.gov/nerlcwww/m_521.pdf
Fan T.Y., Krull I.S., Ross R.D., Wolf M.H., Fine D.H. (1978) Comprehensive analytical procedures for the determination of volatile and non-volatile, polar and non- polarN-nitrosocompounds. In: Environmental Aspects of N-Nitroso Compounds, IARC Scientific Publication No. 19eds WalkerE.A., Castegnaro M., Griciute L., Lyle R.E. pp. 3–17, International Agency for Research on Cancer, Lyon, France.
Fiddler W., Pensabene J.W. (1996) Supercritical fluid extraction of volatile N-nitrosamines in fried bacon and its drippings:method comparison. Journal of AOAC International, 79,895–901.
Fine D.H., Huffman D.P., Rounbehler F., Belcher N.M. (1976a)Analysis of N-nitroso compounds by combined high-performance liquid chromatography and thermal energy analysis. In: Environmental N-Nitroso Compounds: Analysis and Formation, IARC Scientific Publication No. 14edsWalker E.A., Bogovski P., Griciute L. pp. 43–50, International Agency for Research on Cancer, Lyon, France.
Fine D.H., Lieb F.R., Rounbehler D.P. (1975) Description of the thermal energy analyzer (TEA) for trace determination of volatile and non-volatile N-nitroso compounds. Analytical Chemistry, 47, 1188–1191.
Fine D.H., Ross R., Rounbehler D.P., Silvergleid A., Song L.(1976b) Analysis of non-ionic nonvolatile N-nitroso compounds in foodstuffs. Journal of Agricultural and Food Chemistry, 24, 1069–1071.
Fine D.H., Rounbehler D.P. (1975) Trace analysis of volatile N-nitroso compounds by combined gas chromatography and thermal energy analysis. Journal of Chromatography,109,271–279.
Fine D.H., Rounbehler D.P., Yu W.C., Goff E.U. (1984) A new thermal energy analyzer for direct high-performance liquid chromatographic and gas chromatographic analysis of N-nitrosamides. In: N-Nitroso Compounds: Occurrence, BiologicalEffects and Relevance to Human Cancer, IARC Scientific Publication No. 57eds O’Neill I.K., von Borstel R.C., MillerC.T., Long J., Bartsch H. pp. 121–129, International Agency for Research on Cancer, Lyon, France.
Fine D.H., Rounbehler D.R., Sen N.P. (1976c) A comparison of some chromatographic detectors for the analysis of volatile N-nitrosamines. Journal of Agricultural and Food Chemistry, 24,980–984.
Fishbein L. (1979) Overview of some aspects of occurrence, formation and analysis of nitrosamines. Science of the Total Environment, 13, 157–188.
Gloria M.B.A., Barbour J. F., Scanlan R.A. (1997) N-Nitrosodimethylamine in Brazilian, U.S. domestic, and U.S. imported beers. Journal of Agricultural and Food Chemistry, 45,814–816.
Gough T.A. (1978) Determination of N-nitroso compounds by mass spectrometry. Analyst,103, 785–806.
Grebel J.E., Suffet I.H.M. (2007) Nitrogen–phosphorus detection and nitrogen chemiluminescence detection of volatile nitrosamines in water matrices: optimization and performance comparison.Journal of Chromatography A,1175, 141–144.
Greenfield E.L., Smith W.J., Malanoski A.J. (1982a) Mineral–oil vacuum distillation method for nitrosamines in fried bacon, with thermal-energy analyzer– Collaborative study. Journal of the Association of Official Analytical Chemists, 65,1319–1332.
Greenfield E.L., Vasco G.A., Legette L., Malanoski A. (1982b)Screening procedure for detection of volatile N-nitrosamines in cooked bacon by 1-trap mineral oil vacuum distillation and thermal energy analyzer. Journal of the Association of Official Analytical Chemists, 65, 1316–1318.
Hansen T., Archer M.C., Tannenbaum S.R. (1979)Characterization of pyrolysis conditions and interference by other compounds in the chemiluminescence detection of nitrosamines. Analytical Chemistry, 51, 1526–1528.
Hotchkiss J.H. (1981a) Review of analytical methods for N-nitrosamines. Journal of the Association of Official Analytical Chemists, 64, 1037–1054.
Hotchkiss J.H. (1981b) Analytical methodology for sample preparation, detection, quantitation, and confirmation of N-nitrosamines in foods. Journal of the Association of Official Analytical Chemists, 64, 1037–1054.
Hotchkiss J.H., Havery D.C., Fazio T. (1981) A rapid method for estimation of N-nitrosodimethylamine in malt beverages. Journal of the Association of Official Analytical Chemists, 64,929–932.
IARC (1987)Evaluation of the carcinogenic risk of chemicals to humans. Some N-Nitroso Compounds. International Agency for Research on Cancer, IARC Monographs. IARC, Lyon, France.
Izquierdo–Pulido M., Barbour J.F., Scanlan R.S. (1996) N-nitrosodimethylamine in Spanish beers. Food and Chemical Toxicology, 34, 297–299.
Jurado–Sanchez B., Ballesteros E., Gallego M. (2007) Gas chromatographic determination of N-nitrosamines in beverages following automatic solid–phase extraction.Journal of Agricultural and Food Chemistry,55, 9758–9763.
Kimoto W.I., Dooley C.J., Carre J., Fiddler W. (1980) Role of strong ion exchange resins in nitrosamine formation in water. Water Research,14, 869–876.
Kimoto W.I., Fiddler W. (1982) Confirmatory method for N-nitrosodimethylamine and n-nitrosopyrrolidine in food by multiple ion analysis with gas-chromatography low resolution mass-spectrometry before and after ultraviolet photolysis. Journal of the Association of Official Analytical Chemists, 65,1162–1167.
Kubacki S.J. (1979) A survey of methods for determination of non-volatile nitrosamines in food. Pure and Applied Chemistry, 51, 1367–1373.
Libbey L.M., Scanlan R.A. (1985) Mass spectrometry of N–nitrosamines. In Mass Spectrometry in Environmental Sciences eds Karasek F.W., Hutzinger O., Safe S. pp. 537–549, Plenum Publishing Corporation, New York, USA.
Magee P.N., Barnes J.M. (1956) The production of malignant primary hepatic tumours in the rat by feeding dimethylnitrosamine. British Journal of Cancer,10,114–122.
Massey R.C., Key P.E., Jones R.A., Logan G.L. (1991) Volatile, nonvolatile and total N-nitroso compounds in bacon. Food Additives and Contaminants, 8, 585–598.
Massey R.C., Key P.E., McWeeny D.J., Knowles M.E. (1984a) The application of a chemical denitrosation and chemiluminescence detection procedure for estimation of the apparent concentration of total N-nitroso compounds in foods and beverages. Food Additives and Contaminants, 1,11–16.
Massey R.C., Key P.E., McWeeny D.J., Knowles M.E. (1984b)N–nitrosamine analysis in foods: N–nitrosamino acids by high–performance liquid chromatography/thermal energy analysis and total N-nitroso compounds by chemicaldenitrosation/thermal energy analysis. In:N-NitrosoCompounds: Occurrence, Biological Effects and Relevance to Human Cancer, IARC Scientific Publication No. 57eds O’NeillI.K., von Borstel R.C., Miller C.T., Long J., Bartsch H. pp.131–136, International Agency for Research on Cancer, Lyon, France.
Mavelle T., Bouchikhi B., Debry G. (1991a) The occurrence of volatile N-nitrosamines in French foodstuffs.
Food Chemistry, 42, 321–338.
Mavelle T., Bouchikhi B., Debry G. (1991b) Contamination of beer by N-nitrosodimethylamine. Sciences des Aliments, 11,163–170.
Maxwell R.J., Pensabene J.W., Fiddler W. (1993) Multiresidue recovery at ppb levels of 10 nitrosamines from frankfurters by supercritical fluid extraction. Journal of Chromatographic Science, 31, 212–215.
Ohshima H., Kawabata T. (1979) Gas chromatographic separation of hydroxylated N-nitrosamines. Journal of chromatography, 169, 279–286.
Osterdahl B.G. (1991) Occurrence of and exposure to N-nitrosamines in Sweden: a review. IARC Scientific Publications,105, 235–237.
Pan J.W., Song Q., Shi H.H., King M., Junga H., Zhou S.L., WengN.D. (2004) Development, validation and transfer of ahydrophilic interaction liquid chromatography/tandem mass spectrometric method for the analysis of the tobacco-specific nitrosamine metabolite NNAL in human plasma at low picogram per milliliter concentrations. Rapid Communications in Mass Spectrometry,18, 2549–2557.
Pensabene J.W., Fiddler W. (1982) Dual column chromatographic method for determination of N-nitrosothiazolidine in fried bacon. Journal of the Association of Official Analytical Chemists, 65, 1346–1349.
Pensabene J.W., Fiddler W. (2000) Supercritical fluid extraction of nitrosamines from cured meats. In: Supercritical Fluid Methods and Protocols. Methods in Biotechnology, Vol. 13edsWilliams J.R., Clifford A.A. pp. 23–29, Humana Press, Totowa, US.
Pensabene J.W., Green field E.L., Fiddler W. (1982) Rapid dry column method for determination N-nitrosopyrrolidine in fried bacon. Journal of the Association of Official Analytical Chemists,65, 151–156.
Pensabene J.W., Fiddler W., Maxwell R.J., Lightfield A.R., Hampson J.W. (1995) Supercritical-fluid extraction of N-nitrosamines in hams processed in elastic rubber nettings. Journal of AOAC International,78, 744–748.
Perez D.M., Alatorre G.G., Alvarez E.B., Silva E.E., Alvarado J.F.J. (2008) Solid–phase microextraction of N-nitrosodimethylamine in beer. Food Chemistry,107,1348–1352.
Pignatelli B., Richard I., Bourgade M.C., Bartsch H. (1987) An improved method for analysis of total N-nitroso compounds in gastric juice. In: Relevance of N-nitroso Compounds to Human Cancer: Exposures and Mechanisms, IARC Scientific Publication No. 87eds Bartsch H., O’Neill I.K.,Schultz–Hermann R. pp. 209–215, International Agency for Research on Cancer, Lyon, France.
Pignatelli B., Walters C.L. (1996) Analytical techniques for total N-nitroso compounds. European Journal of Cancer Prevention, 5, 51–58.
Preussmann R., Stewart B.W. (1984) N-nitroso carcinogens. In: Chemical Carcinogens. ACS Monograph 182,Vol. 2ed Searle C.E. pp. 643–828, American Chemical Society, Washington, US.
Rainey W.T, Christie W.H., Lijinsky W. (1978) Mass spectrometry of N-nitrosamines. Biomedical Mass Spectrometry, 5, 395–408.
Raoul S., Gremaud E., Biaudet H., Turesky R.J. (1997) Rapidsolid-phase extraction method for the detection of volatile nitrosamines in food. Journal of Agricultural and Food Chemistry, 45, 4706–4713.
Rath S., Reyes F.G. (2009) Nitrosamines. In: Handbook of Processed Meats and Poultry Analysis eds Nollet L.M.L., ToldraF. pp. 687–704, CRC Press, Boca Raton, US.
Scanlan R.A. (1984) Chemiluminescence for measurement of N–nitrosamines in foods. In: Analysis of Food Contaminants ed Gilbert J. pp. 321–376, Elsevier, UK.
Scanlan R.A., Reyes F.G. (1985) An update on analytical techniques for N-nitrosamines. Food Technology, 39, 95–99.
Sen N.P. (1970) Gas–liquid chromatographic determination of dimethylnitrosamine as dimethylnitramine at picogram levels. Journal of Chromatography,51, 301–304.
Sen N.P. (1984) Recent trends in the analysis of nitrosamines in food. In: Food Constituents and Food Residues: Their Chromatographic Determination ed Lawrence J.F. pp. 453–488, Marcel Dekker Inc., US.
Sen N.P., Seaman S. (1981) An investigation into the possible presence of volatile nitrosamines in cooking oils, margarine and butter. Journal of Agricultural and Food Chemistry, 29,787–789.
Sen N.P., Seaman S.W., Bergeron C., Brousseau R.J. (1996) Trends in the levels of N-nitrosodimethylamine in Canadian and imported beers. Journal of Agricultural and Food Chemistry, 44,1498–1501.
Sen N.P., Seaman S.W., Page B.D. (1997) Rapid semi–quantitativeestimation of N-nitrosodibutylamine and N-nitrosodibenzylamine in smoked hams by solid-phase microextraction followed by gas chromatography-thermal energy analysis.Journal of Chromatography A,788, 131–140.
Song P.J., Hu J.F. (1988) N-Nitrosamines in Chinese foods. Food and Chemical Toxicology, 26, 205–208.
Takatsuki K., Kikuchi T. (1990) Determination of N-nitrosodimethylamine in fish products using gas-chromatography with nitrogen phosphorus detection. Journal of Chromatography, 508, 357–362.
Tricker A.R. (1997)N-nitroso compounds and man: sources of exposure, endogenous formation and occurrence in body fluids. European Journal of Cancer Prevention, 6, 226–268.
Tricker A.R., Kubacki S.J. (1992) Review of the occurrence and formation of nonvolatile N-nitroso compounds in foods. Food Additives and Contaminants, 9, 39–69.
USDA (2005) Code of Federal Regulations – Title 21: Food and Drugs – 21 CFR 179.26 – Ionizing radiation for the treatment of food. Title 9 – Animals and animal products. Chapter III –Food Safety and Inspection Service, Department ofAgriculture. Subchapter E – Regulatory requirements under the federal meat inspection act and the poultry products inspection act. Part 424 – Preparation and processing operations. Subpart c – Food ingredients and sources of radiation. 424.22 – Certain other permitted uses. Available at http://cfr.vlex.com/vid/22-certain-other-permitted-uses-19611025
Ventanas S., Martin D., Estevez M., Ruiz J. (2006) Analysis of volatile nitrosamines from a model system using SPME-DED at different temperatures and times of extraction. Food Chemistry,99, 842–850.
Walker E.A., Castegnaro M. (1975) A report on the present status of a collaborative study of methods for the trace analysis of volatile nitrosamines. In: N-Nitroso Compounds in the Environment, IARC Scientific Publication No. 9eds Bogovski P., Walker E.A. pp. 57–62, International Agency for Research on Cancer, Lyon, France.
Walker E.A., Castegnaro M. (1980) Response of nitramines in the thermal analyzer. Journal of Chromatography,187, 229–231.
Walters C.L. (1996) Analytical techniques for the determination of total N-nitroso compounds. European Journal of Cancer Prevention, 5, 59–61.
Walters C.L., Hart R.J., Smith P.L.R. (1983) Analysis of total N-nitroso compounds as a group by denitrosation to nitric oxide, with detection using a chemiluminescence analyser. In: N-Nitroso Compounds, IARC Scientific Publication No. 45, Vol. 6eds Preussmann R., O’Neill I.K., Eisenbrand G., Spiegelhalder B., Bartsch H. pp. 295–308, International Agency for Research on Cancer, Lyon, France.
Walters C.L., Smith P.L.R., Reed P.I. (1984) Pitfalls to avoid in determining N-nitroso compounds as a group. In: N-nitroso Compounds: Occurrence, Biological Effects and Relevance to Human Cancer, IARC Scientific Publication No. 57eds O’NeillI.K., von Borstel R.C., Miller C.T., Long J., Bartsch H.pp. 113–120, International Agency for Research on Cancer, Lyon, France.
Webb K.S., Gough T.A. (1979) Suppression of chemiluminescent detector response toward nitrosamines. Journal of Chromatography, 177, 349–352.
Webb K.S., Libbey L.M., Hotchkiss J.H., Scanlan R.A., Fazio T., Castegnaro M. (1983) Mass spectrometric analysis of N–nitroso compounds and derivatives. In: Environmental Carcinogens: Selected Methods of Analysis, Vol. 6 N-nitroso Compounds eds Egan H., Preussmann R., O’Neill I.K., Eisenbrand G., Spiegelhalder B., Bartsch H. pp. 449–462, International Agency for Research on Cancer, Lyon, France.
Yurchenko S. (2006) Determination of some carcinogenic contaminants in food. Dissertationes Chimicae Universitatis Tartuensis 51, Tartu University Press. Available at https://dspace.utlib.ee/xmlui/bitstream/handle/10062/1268/jurchenko.pdf?sequence=5
Yurchenko S., Molder U. (2005)N-nitrosodimethylamineanalysis in Estonian beer using positive-ion chemical ionization with gas chromatography mass spectrometry. Food Chemistry, 89, 455–463.
Yurchenko S., Molder U. (2007) The occurrence of volatile N-nitrosamines in Estonian meat products. Food Chemistry, 100,1713–1721.
Andrade R., Reyes F.G.R., Rath S. (2005) A method for the determination of volatile N–nitrosamines in food by HS–SPME–GC–TEA. Food Chemistry,91, 173–179.
AOAC (2004) Official Methods of Analysis of the Association of Official Analytical Chemists, 19th Edition. Association of Official Analytical Chemists, USA.
Bartsch H., Spiegelhalder B. (1996) Environmental exposure to N-nitroso compounds (NNOC) and precursors: an overview. European Journal of Cancer Prevention,5, 11–17.
Baxter E.D., Slaiding I.R., Travers V. (2007) Current incidence of N-nitrosodimethylamine in beers worldwide. Food Additives and Contaminants, 24, 807–811.
Bellec G., Cauvin J.M., Salaun M.C., LeCalve K., Dreano Y., Gouerou H., Menez J.F., Berthou F. (1996) Analysis of N–nitrosamines by high-performance liquid chromatography with post–column photohydrolysis and colorimetric detection. Journal of Chromatography A,727, 83–92.
Biaudet H., Mavelle T., Debry G. (1994) Mean daily intake of N-nitrosodimethylamine from foods and beverages in France in1987–1992. Food Chemistry and Toxicology,32, 417–421.
Borwitzky H. (1986) Some improvements in the determination of volatile nitrosamines by fused silica capillary-GC in combination with a thermal energy analyzer. Chromatographia, 22, 65–72.
Bouchikhi B., Mavelle T., Debry G. (1989) Precautions to be taken in the analysis of total N-nitroso compounds. Food Additives and Contaminants, 6, 209–217.
Budeveska B.O., Rizov N.A., Gheoghiev G.K. (1986) Photolytic chemiluminescence detector for gas chromatographic analysis of N-nitroso compounds. Journal of Chromatography, 351,501–505.
Cardenes L., Ayala J.H., Gonzalez V., Afonso A.M. (2002a) Fastmicrowave–assisted dansylation of N-nitrosamines – Analysisby high-performance liquid chromatography with fluorescence detection. Journal of Chromatography A,946,133–140.
Cardenes L., Ayala J.H., Gonzalez V., Afonso A.M. (2002b)Determination of N-nitrosodimethylamine by HPLC, with fluorescence detection. A survey of N-nitrosodimethylaminein commercial beers. Journal of Liquid Chromatography andRelated Technologies,25, 977–984.
Castegnaro M., Massey R.C., Walters C.L. (1987) The collaborative evaluation of a procedure for the determination of N-nitroso compounds as a group. Food Additives and Contaminants, 4, 37–43.
Castegnaro M., Webb K.S. (1983) Detection techniques –Introduction. In: Environmental carcinogens – selected methods of analysis.6.N-nitroso compounds, Vol. 45 eds Preussman R, O’Neil L, Eisenbrand G, Spiegelhalder B, Bartsch B. pp.439–447, International Agency for Research on Cancer, Lyon, France.
Challis B.C., Colling J., Cromie D.D.O., Guthrie W.G., PollockJ.R.A., Taylor P., Telling G.M., Wallace L. (1995) A screening procedure for total N-nitroso contaminants in personal care products: results of collaborative studies undertaken by a CTPA Working Group. International Journal of Cosmetic Science,17, 219–231.
Choi J., Valentine R.L. (2002) Formation of N-nitrosodimethylamine (NDMA) from reaction of monochloroamine: a new disinfection by-product. Water Research, 36, 817–824.
Conboy J.J., Hotchkiss J.H. (1989) Photolytic interface for high–performance liquid-chromatography chemiluminescence detection of non-volatile N-nitrosocompounds. Analyst, 114, 155–159.
Crosby N.T. (1976) Nitrosamines in foodstuffs. Residue Reviews, 64, 77–135.
Crosby N.T, Sawyer R. (1976)N-nitrosamines: a review of chemical and biological properties and their estimation in foodstuffs. Advances in Food Research,22, 1–71.
Cutaia A.J. (1982) Malt beverages and brewing materials: screening and confirmatory methods for nitrosamines in beer. Journal of the Association of Official Analytical Chemists, 65,584–587.
Eisenbrand G., Arch M., Brunnemann K.D., Fine D.H., HechtS.S., Hoffmann D., Krull J., Webb K.S. (1983) Problems of contamination and artifact formation in nitrosamine sampling and analysis. In: N-Nitroso Compounds, IARC Scientific Publication No. 45, Vol. 6eds Preussmann R., O’Neill I.K., Eisenbr and G., Spiegelhalder B., Bartsch H. pp. 25–34, International Agency for Research on Cancer, Lyon, France.
Eisenbrand G., Janzowski C., Preussmann R. (1976) Gas chromatographic determination of nitrosamino acids by trimethylsilylation and single-ion monitoring in a gas chromatography-mass spectrometry system. In: Environmental N-Nitroso Compounds: Analysis and Formation, IARC Scientific Publication No. 14eds Walker E.A., Bogovski P., Griciute L. pp. 21–26, International Agency for Research on Cancer, Lyon, France.
Ender F., Havre G., Helgebostad A., Koppang N., Masden R., CehL. (1964) Isolation and identification of a hepatotoxic factor in herring meat produced from sodium nitrite preserved herring. Naturwissenschaften, 51, 637–638.
EPA (1997) US Environmental Protection Agency, N-Nitrosodimethylamine, CASRN 62–75–9, Integrated Risk Information System (IRIS) Substance File, 1993. Available at http://www.epa.gov/iris/subst/0045.htm
EPA (2004) Method 521: Determination of nitrosamines in drinking water by solid phase extraction and capillary column gas chromatography with large volume injection and chemical ionization tandem mass spectrometry (MS/MS), Ver.1.0, EPA Document # EPA/600/R–05/054. Available at http://www.epa.gov/nerlcwww/m_521.pdf
Fan T.Y., Krull I.S., Ross R.D., Wolf M.H., Fine D.H. (1978) Comprehensive analytical procedures for the determination of volatile and non-volatile, polar and non- polarN-nitrosocompounds. In: Environmental Aspects of N-Nitroso Compounds, IARC Scientific Publication No. 19eds WalkerE.A., Castegnaro M., Griciute L., Lyle R.E. pp. 3–17, International Agency for Research on Cancer, Lyon, France.
Fiddler W., Pensabene J.W. (1996) Supercritical fluid extraction of volatile N-nitrosamines in fried bacon and its drippings:method comparison. Journal of AOAC International, 79,895–901.
Fine D.H., Huffman D.P., Rounbehler F., Belcher N.M. (1976a)Analysis of N-nitroso compounds by combined high-performance liquid chromatography and thermal energy analysis. In: Environmental N-Nitroso Compounds: Analysis and Formation, IARC Scientific Publication No. 14edsWalker E.A., Bogovski P., Griciute L. pp. 43–50, International Agency for Research on Cancer, Lyon, France.
Fine D.H., Lieb F.R., Rounbehler D.P. (1975) Description of the thermal energy analyzer (TEA) for trace determination of volatile and non-volatile N-nitroso compounds. Analytical Chemistry, 47, 1188–1191.
Fine D.H., Ross R., Rounbehler D.P., Silvergleid A., Song L.(1976b) Analysis of non-ionic nonvolatile N-nitroso compounds in foodstuffs. Journal of Agricultural and Food Chemistry, 24, 1069–1071.
Fine D.H., Rounbehler D.P. (1975) Trace analysis of volatile N-nitroso compounds by combined gas chromatography and thermal energy analysis. Journal of Chromatography,109,271–279.
Fine D.H., Rounbehler D.P., Yu W.C., Goff E.U. (1984) A new thermal energy analyzer for direct high-performance liquid chromatographic and gas chromatographic analysis of N-nitrosamides. In: N-Nitroso Compounds: Occurrence, BiologicalEffects and Relevance to Human Cancer, IARC Scientific Publication No. 57eds O’Neill I.K., von Borstel R.C., MillerC.T., Long J., Bartsch H. pp. 121–129, International Agency for Research on Cancer, Lyon, France.
Fine D.H., Rounbehler D.R., Sen N.P. (1976c) A comparison of some chromatographic detectors for the analysis of volatile N-nitrosamines. Journal of Agricultural and Food Chemistry, 24,980–984.
Fishbein L. (1979) Overview of some aspects of occurrence, formation and analysis of nitrosamines. Science of the Total Environment, 13, 157–188.
Gloria M.B.A., Barbour J. F., Scanlan R.A. (1997) N-Nitrosodimethylamine in Brazilian, U.S. domestic, and U.S. imported beers. Journal of Agricultural and Food Chemistry, 45,814–816.
Gough T.A. (1978) Determination of N-nitroso compounds by mass spectrometry. Analyst,103, 785–806.
Grebel J.E., Suffet I.H.M. (2007) Nitrogen–phosphorus detection and nitrogen chemiluminescence detection of volatile nitrosamines in water matrices: optimization and performance comparison.Journal of Chromatography A,1175, 141–144.
Greenfield E.L., Smith W.J., Malanoski A.J. (1982a) Mineral–oil vacuum distillation method for nitrosamines in fried bacon, with thermal-energy analyzer– Collaborative study. Journal of the Association of Official Analytical Chemists, 65,1319–1332.
Greenfield E.L., Vasco G.A., Legette L., Malanoski A. (1982b)Screening procedure for detection of volatile N-nitrosamines in cooked bacon by 1-trap mineral oil vacuum distillation and thermal energy analyzer. Journal of the Association of Official Analytical Chemists, 65, 1316–1318.
Hansen T., Archer M.C., Tannenbaum S.R. (1979)Characterization of pyrolysis conditions and interference by other compounds in the chemiluminescence detection of nitrosamines. Analytical Chemistry, 51, 1526–1528.
Hotchkiss J.H. (1981a) Review of analytical methods for N-nitrosamines. Journal of the Association of Official Analytical Chemists, 64, 1037–1054.
Hotchkiss J.H. (1981b) Analytical methodology for sample preparation, detection, quantitation, and confirmation of N-nitrosamines in foods. Journal of the Association of Official Analytical Chemists, 64, 1037–1054.
Hotchkiss J.H., Havery D.C., Fazio T. (1981) A rapid method for estimation of N-nitrosodimethylamine in malt beverages. Journal of the Association of Official Analytical Chemists, 64,929–932.
IARC (1987)Evaluation of the carcinogenic risk of chemicals to humans. Some N-Nitroso Compounds. International Agency for Research on Cancer, IARC Monographs. IARC, Lyon, France.
Izquierdo–Pulido M., Barbour J.F., Scanlan R.S. (1996) N-nitrosodimethylamine in Spanish beers. Food and Chemical Toxicology, 34, 297–299.
Jurado–Sanchez B., Ballesteros E., Gallego M. (2007) Gas chromatographic determination of N-nitrosamines in beverages following automatic solid–phase extraction.Journal of Agricultural and Food Chemistry,55, 9758–9763.
Kimoto W.I., Dooley C.J., Carre J., Fiddler W. (1980) Role of strong ion exchange resins in nitrosamine formation in water. Water Research,14, 869–876.
Kimoto W.I., Fiddler W. (1982) Confirmatory method for N-nitrosodimethylamine and n-nitrosopyrrolidine in food by multiple ion analysis with gas-chromatography low resolution mass-spectrometry before and after ultraviolet photolysis. Journal of the Association of Official Analytical Chemists, 65,1162–1167.
Kubacki S.J. (1979) A survey of methods for determination of non-volatile nitrosamines in food. Pure and Applied Chemistry, 51, 1367–1373.
Libbey L.M., Scanlan R.A. (1985) Mass spectrometry of N–nitrosamines. In Mass Spectrometry in Environmental Sciences eds Karasek F.W., Hutzinger O., Safe S. pp. 537–549, Plenum Publishing Corporation, New York, USA.
Magee P.N., Barnes J.M. (1956) The production of malignant primary hepatic tumours in the rat by feeding dimethylnitrosamine. British Journal of Cancer,10,114–122.
Massey R.C., Key P.E., Jones R.A., Logan G.L. (1991) Volatile, nonvolatile and total N-nitroso compounds in bacon. Food Additives and Contaminants, 8, 585–598.
Massey R.C., Key P.E., McWeeny D.J., Knowles M.E. (1984a) The application of a chemical denitrosation and chemiluminescence detection procedure for estimation of the apparent concentration of total N-nitroso compounds in foods and beverages. Food Additives and Contaminants, 1,11–16.
Massey R.C., Key P.E., McWeeny D.J., Knowles M.E. (1984b)N–nitrosamine analysis in foods: N–nitrosamino acids by high–performance liquid chromatography/thermal energy analysis and total N-nitroso compounds by chemicaldenitrosation/thermal energy analysis. In:N-NitrosoCompounds: Occurrence, Biological Effects and Relevance to Human Cancer, IARC Scientific Publication No. 57eds O’NeillI.K., von Borstel R.C., Miller C.T., Long J., Bartsch H. pp.131–136, International Agency for Research on Cancer, Lyon, France.
Mavelle T., Bouchikhi B., Debry G. (1991a) The occurrence of volatile N-nitrosamines in French foodstuffs.
Food Chemistry, 42, 321–338.
Mavelle T., Bouchikhi B., Debry G. (1991b) Contamination of beer by N-nitrosodimethylamine. Sciences des Aliments, 11,163–170.
Maxwell R.J., Pensabene J.W., Fiddler W. (1993) Multiresidue recovery at ppb levels of 10 nitrosamines from frankfurters by supercritical fluid extraction. Journal of Chromatographic Science, 31, 212–215.
Ohshima H., Kawabata T. (1979) Gas chromatographic separation of hydroxylated N-nitrosamines. Journal of chromatography, 169, 279–286.
Osterdahl B.G. (1991) Occurrence of and exposure to N-nitrosamines in Sweden: a review. IARC Scientific Publications,105, 235–237.
Pan J.W., Song Q., Shi H.H., King M., Junga H., Zhou S.L., WengN.D. (2004) Development, validation and transfer of ahydrophilic interaction liquid chromatography/tandem mass spectrometric method for the analysis of the tobacco-specific nitrosamine metabolite NNAL in human plasma at low picogram per milliliter concentrations. Rapid Communications in Mass Spectrometry,18, 2549–2557.
Pensabene J.W., Fiddler W. (1982) Dual column chromatographic method for determination of N-nitrosothiazolidine in fried bacon. Journal of the Association of Official Analytical Chemists, 65, 1346–1349.
Pensabene J.W., Fiddler W. (2000) Supercritical fluid extraction of nitrosamines from cured meats. In: Supercritical Fluid Methods and Protocols. Methods in Biotechnology, Vol. 13edsWilliams J.R., Clifford A.A. pp. 23–29, Humana Press, Totowa, US.
Pensabene J.W., Green field E.L., Fiddler W. (1982) Rapid dry column method for determination N-nitrosopyrrolidine in fried bacon. Journal of the Association of Official Analytical Chemists,65, 151–156.
Pensabene J.W., Fiddler W., Maxwell R.J., Lightfield A.R., Hampson J.W. (1995) Supercritical-fluid extraction of N-nitrosamines in hams processed in elastic rubber nettings. Journal of AOAC International,78, 744–748.
Perez D.M., Alatorre G.G., Alvarez E.B., Silva E.E., Alvarado J.F.J. (2008) Solid–phase microextraction of N-nitrosodimethylamine in beer. Food Chemistry,107,1348–1352.
Pignatelli B., Richard I., Bourgade M.C., Bartsch H. (1987) An improved method for analysis of total N-nitroso compounds in gastric juice. In: Relevance of N-nitroso Compounds to Human Cancer: Exposures and Mechanisms, IARC Scientific Publication No. 87eds Bartsch H., O’Neill I.K.,Schultz–Hermann R. pp. 209–215, International Agency for Research on Cancer, Lyon, France.
Pignatelli B., Walters C.L. (1996) Analytical techniques for total N-nitroso compounds. European Journal of Cancer Prevention, 5, 51–58.
Preussmann R., Stewart B.W. (1984) N-nitroso carcinogens. In: Chemical Carcinogens. ACS Monograph 182,Vol. 2ed Searle C.E. pp. 643–828, American Chemical Society, Washington, US.
Rainey W.T, Christie W.H., Lijinsky W. (1978) Mass spectrometry of N-nitrosamines. Biomedical Mass Spectrometry, 5, 395–408.
Raoul S., Gremaud E., Biaudet H., Turesky R.J. (1997) Rapidsolid-phase extraction method for the detection of volatile nitrosamines in food. Journal of Agricultural and Food Chemistry, 45, 4706–4713.
Rath S., Reyes F.G. (2009) Nitrosamines. In: Handbook of Processed Meats and Poultry Analysis eds Nollet L.M.L., ToldraF. pp. 687–704, CRC Press, Boca Raton, US.
Scanlan R.A. (1984) Chemiluminescence for measurement of N–nitrosamines in foods. In: Analysis of Food Contaminants ed Gilbert J. pp. 321–376, Elsevier, UK.
Scanlan R.A., Reyes F.G. (1985) An update on analytical techniques for N-nitrosamines. Food Technology, 39, 95–99.
Sen N.P. (1970) Gas–liquid chromatographic determination of dimethylnitrosamine as dimethylnitramine at picogram levels. Journal of Chromatography,51, 301–304.
Sen N.P. (1984) Recent trends in the analysis of nitrosamines in food. In: Food Constituents and Food Residues: Their Chromatographic Determination ed Lawrence J.F. pp. 453–488, Marcel Dekker Inc., US.
Sen N.P., Seaman S. (1981) An investigation into the possible presence of volatile nitrosamines in cooking oils, margarine and butter. Journal of Agricultural and Food Chemistry, 29,787–789.
Sen N.P., Seaman S.W., Bergeron C., Brousseau R.J. (1996) Trends in the levels of N-nitrosodimethylamine in Canadian and imported beers. Journal of Agricultural and Food Chemistry, 44,1498–1501.
Sen N.P., Seaman S.W., Page B.D. (1997) Rapid semi–quantitativeestimation of N-nitrosodibutylamine and N-nitrosodibenzylamine in smoked hams by solid-phase microextraction followed by gas chromatography-thermal energy analysis.Journal of Chromatography A,788, 131–140.
Song P.J., Hu J.F. (1988) N-Nitrosamines in Chinese foods. Food and Chemical Toxicology, 26, 205–208.
Takatsuki K., Kikuchi T. (1990) Determination of N-nitrosodimethylamine in fish products using gas-chromatography with nitrogen phosphorus detection. Journal of Chromatography, 508, 357–362.
Tricker A.R. (1997)N-nitroso compounds and man: sources of exposure, endogenous formation and occurrence in body fluids. European Journal of Cancer Prevention, 6, 226–268.
Tricker A.R., Kubacki S.J. (1992) Review of the occurrence and formation of nonvolatile N-nitroso compounds in foods. Food Additives and Contaminants, 9, 39–69.
USDA (2005) Code of Federal Regulations – Title 21: Food and Drugs – 21 CFR 179.26 – Ionizing radiation for the treatment of food. Title 9 – Animals and animal products. Chapter III –Food Safety and Inspection Service, Department ofAgriculture. Subchapter E – Regulatory requirements under the federal meat inspection act and the poultry products inspection act. Part 424 – Preparation and processing operations. Subpart c – Food ingredients and sources of radiation. 424.22 – Certain other permitted uses. Available at http://cfr.vlex.com/vid/22-certain-other-permitted-uses-19611025
Ventanas S., Martin D., Estevez M., Ruiz J. (2006) Analysis of volatile nitrosamines from a model system using SPME-DED at different temperatures and times of extraction. Food Chemistry,99, 842–850.
Walker E.A., Castegnaro M. (1975) A report on the present status of a collaborative study of methods for the trace analysis of volatile nitrosamines. In: N-Nitroso Compounds in the Environment, IARC Scientific Publication No. 9eds Bogovski P., Walker E.A. pp. 57–62, International Agency for Research on Cancer, Lyon, France.
Walker E.A., Castegnaro M. (1980) Response of nitramines in the thermal analyzer. Journal of Chromatography,187, 229–231.
Walters C.L. (1996) Analytical techniques for the determination of total N-nitroso compounds. European Journal of Cancer Prevention, 5, 59–61.
Walters C.L., Hart R.J., Smith P.L.R. (1983) Analysis of total N-nitroso compounds as a group by denitrosation to nitric oxide, with detection using a chemiluminescence analyser. In: N-Nitroso Compounds, IARC Scientific Publication No. 45, Vol. 6eds Preussmann R., O’Neill I.K., Eisenbrand G., Spiegelhalder B., Bartsch H. pp. 295–308, International Agency for Research on Cancer, Lyon, France.
Walters C.L., Smith P.L.R., Reed P.I. (1984) Pitfalls to avoid in determining N-nitroso compounds as a group. In: N-nitroso Compounds: Occurrence, Biological Effects and Relevance to Human Cancer, IARC Scientific Publication No. 57eds O’NeillI.K., von Borstel R.C., Miller C.T., Long J., Bartsch H.pp. 113–120, International Agency for Research on Cancer, Lyon, France.
Webb K.S., Gough T.A. (1979) Suppression of chemiluminescent detector response toward nitrosamines. Journal of Chromatography, 177, 349–352.
Webb K.S., Libbey L.M., Hotchkiss J.H., Scanlan R.A., Fazio T., Castegnaro M. (1983) Mass spectrometric analysis of N–nitroso compounds and derivatives. In: Environmental Carcinogens: Selected Methods of Analysis, Vol. 6 N-nitroso Compounds eds Egan H., Preussmann R., O’Neill I.K., Eisenbrand G., Spiegelhalder B., Bartsch H. pp. 449–462, International Agency for Research on Cancer, Lyon, France.
Yurchenko S. (2006) Determination of some carcinogenic contaminants in food. Dissertationes Chimicae Universitatis Tartuensis 51, Tartu University Press. Available at https://dspace.utlib.ee/xmlui/bitstream/handle/10062/1268/jurchenko.pdf?sequence=5
Yurchenko S., Molder U. (2005)N-nitrosodimethylamineanalysis in Estonian beer using positive-ion chemical ionization with gas chromatography mass spectrometry. Food Chemistry, 89, 455–463.
Yurchenko S., Molder U. (2007) The occurrence of volatile N-nitrosamines in Estonian meat products. Food Chemistry, 100,1713–1721.
Article Sidebar
Published
Mar 31, 2010
Article Details
Issue
Section
Review Article
