W-nitrosamines

W-nitrosodiethylamine from soil by wheat, barley and several vegetable crops has been demonstrated (17,18). Rapid disappearance of the N-nitrosoamine absorbed by plants was observed. Sander et al. (19) observed that several W-nitrosoamines could be removed from water by cress, but the residues rapidly decreased when W-nitrosamine containing water was replaced with non-contaminated water. Dean-Raymond and Alexander (20) reported... 

SEN N p, BADDON p A and SEAMAN s w, Nitrosamines in cured pork products packaged in elastic rubber netting an update , Food Chemistry, 1993 47(4) 387-390. 

Sen, N.P., Donaldson, B.A., Seaman, S., Iyengar, J.R., Miles, W.F. Paper presented at Symp. Nitrosamines in Cheese, 1977, Ottawa, Canada... 

Hickman, D.H. Hardwick, W.A. Ladish, W.J. Meilgaard, M.C. Jangaard, N.O. "Technical Report of the United States Brewers Association Ad Hoc Committee on Nitrosamines Master Brewers Association of America, Technical Quart. In press (1981). Scanlan, R.A. O Brien, T.J. Unpublished data. 

The persistence of the N-nitrosamine that may be formed in soil will depend on a host of conditions, such as soil type, organic matter content, clay content, pH, the microflora present in the soil, moisture content and temperature, etc. Superimposed on all these factors will be the chemical nature of the pesticide. The N-nitrosoatrazine ( ) formed in soil from the herbicide atrazine ( ) was shown to be rapidly disappeared (1). Thus, in soil W-nitrosoatrazine was observed after one week, but was absent 4 and 10 weeks later (Table IV). In contrast, N-nitroso-butralin (11 ) persisted much longer than N-nitrosoatrazine (9) under the same conditions (Table V) and was still detectable after 6 months (3). Our studies demonstrated that N-nitrosoglyphosate is persistent in the soil. Fox soil treated with 20 ppm of nitrite nitrogen and 740 ppm glyphosate contained about 7 ppm of N-nitrosoglyphosate even after 140 days (6). 

B.G. Willoughby and K.W. Scott, Nitrosamines in Rubber, Rapra Technology Ltd, Shawbury (1997). 

Synonyms AI3-25308 BRN 1738979 CCRIS 261 Dimethylnitrosamine W-Dimethyl-nitrosamine A,A-Dimethylnitrosamine Dimethylnitrosomine DMN DMNA EINECS 200-549-8 A-Methyl-A/ nitrosomethanamine NDMA Nitrous dimethylamide NSC 23226 RCRA waste number P082. 

Letterman RD (ed) (1999) Water quality and treatment A handbook of community water supplies, 5th ed., Amer. Water Works Assoc., McGraw-Hill, New York Lijinsky W, Epstein SS (1970) Nitrosamines as environmental carcinogens. Nature 225 21-23 Lin S, Marshall EG, Davidson GK (1994) Potential parental exposure to pesticides and hmb reduction defects. Scand J Work Environ Health 20 166-179 Linak, E, Lutz, HJ, Nakamura E (1990) Chlorinated Solvents. In Linak E, Lutz HJ, Nakamura E, C2 chlorinated solvents, chemical economics handbook, Stanford Research Institute, Menlo Park, CA, pp. 632.30000a-632.3001z Lindsay WL (1979) Chemical equilibria in soils. John Wiley, New York... 

Lijinsky W, Reuber MD Comparative carcinogenesis by some aliphatic nitrosamines in Fischer rats. Cancer Lett 14 297-302, 1981... 

White, J. F. Foley, R. R. Maronpot, and NT108 M. W. Anderson. Role of Clara cells and type II cells in the development of pulmonary tumors in rats and mice following exposure to a tobacco-specific nitrosamine. Exp Lung Res 1991 ... 

Tannenbaum, S. R. Sinskey, A. J. Weisman, M. Bishop, W. Nitrite in human saliva. Its possible relationship to nitrosamine formation. J. Natl. Cancer Inst., 1974, 53, 79-84. 

Nitrosamines , Nakahara, W., Takayama S., Sugimura, T. and Odashima, S. Eds., Procedings of the Second International Symposium of the Princess Takamatsu Cancer Research Fund, Tokyo Press, Tokyo, 19l72, 213-235. 

Syndex, C.M./ Farelly, J.G. and Lijinsky, W., Metabolism of Three Cyclic Nitrosamines in Sprague Dawley Rats , Cancer Res, 1 77, 37, 3530--3532. 

AAF, 2-acetylaminofluorene BBN, W-butyl-W-(4-hydroxybutyl)nitrosamine EHEN, W-ethyl-W-hydroxyethylnitrosamine NDEA, W-nitrosodiethylamine F, female M, male i.p., intraperitoneal injection i.g., intragastric PEI, partial hepatectomy... 

Lethco, E.J., Wallace, W.C. Brouwer, E. (1982) The fate of V-nitrosodiethanolamine after oral and tropical administration to rats. Food chem. Toxicol, 20, 401 06 Lijinsky, W. Andrews, A.W (1983) The superiority of hamster liver microsomal fraction for activating nitrosamines to mutagens in Salmonella typhimurium. Mutat. Res., Ill, 135-144 Lijinsky, W. Kovatch, R. (1985) Induction of liver tumoms in rats by nitrosodiethanolamine at low doses. Carcinogenesis, 6, 1679-1681... 

Lijinsky, W., Losikoff, A.M. Sansone, E.B. (1981) Penetration of rat skin by A-nitrosodi-ethanolamine and A-nitrosomorpholine. J. natl Cancer Inst, 66, 125-127 Lijinsky, W., Saavedra, J.E. Kovateh, R.M. (1988) Careinogenesis and nucleic acid alkylation by some oxygenated nitrosamines in rats and hamsters. Chem.-biol Interact, 66, 37 7 Loeppky, R.N. (1999) The mechanism of bioactivation of A-nitrosodiethanolamine. Drug Metab. Rev., 31, 175-193... 

Mergens, W. J., Kamm, J. J., Newmark, H. L., Fiddler, W., and Pensabene, J. (1978). Alpha-tocopherol Uses in preventing nitrosamine formation. In Environmental Aspects of N-Nitroso Compounds (E. A. Walker, L. Griciute, M. Castegnaro, and R. E. Lyle, eds.), pp. 199-212. lARC Scientific Publication NO. 19. International Agency for Research on Cancer, Lyon, France. 

The GC-TEA conditions used for the detection of volatile nitrosamines have been described by Fine and Rounbehler (8). A 14 x 1/8" stainless steel column packed with 5% Carbowax 20M containing 2% NaOH on Chromosorb W HP (80-100 mesh) was operated at 175°C with argon gas as the carrier at a flow rate of 15 mL/min. A TEA was used as the detector with dry ice/ethanol as the cold trap. The HPLC-TEA was constructed by sequentially connecting a high pressure pump (Altex, model 110), an injector (Waters, model U6K), a yPorasil column (Waters), and a TEA. The operation of HPLC-TEA has been described by Fine, et al.( ). 

Rounbehler, D.P. Reisch, J.W. Coombs, J.R. and Fine, D.H., "Nitrosamine Air Sampling Sorbents Compared for Quantitative Collection and Artifact Formation" Anal. Chem. 1980, 52, 273-276. 

Zijlstra, J.A. Vogel, E.W (1988) Influence of inhibition of the metabolic activation on the mutagenicity of some nitrosamines, triazenes, hydrazines and seniciphylline in Drosophila melanogaster. Mutat. Res., 202, 251-267... 

N-Nitrosodiethylamine. Add 36-5 g. (51-5 ml.) of diethylamine slowly to the calculated quantity of carefully standardised 5IV-hydro chloric acid cooled in ice (1). Introduce the solution of the hydrochloride into a solution of 39 g. of sodium nitrite (assumed to be of 90 per cent, purity) in 45 ml. of w ater contained in a 250 ml. distilling flask. Distil the mixture rapidly to dryness. Separate the yellow upper layer of the nitrosamine from the distillate saturate the aqueous layer with solid potassium carbonate and remove the nitroso compound which separates and add it to the main product. Dry over anhydrous potassium carbonate and distil. Collect the diethylnitrosamine at 172 173-5°. The yield is 41 g. 

Fiddler, W., et al. Some Current Observations on the Occurrence and Formation of N-nitrosamines, Proc, 18th Meeting Meat Res. Workers, Guelph, Ontario, Canada, 1972. 

N 20.40%, crysts(from HN03), mp 87 8° easily sol in benz, chlf or boiling methanol or ethanol si sol in cold methanol. Can be prepared either by crystn of the corresponding nitrosamine from HN03 or by nitration of 2-nitro-N-butylamino-toluene with HNOg(d 1.5) as described in Ref 2. Its expl props were not investigated Refs l)Beil 12, (445) 2)J.Reilly W.J. Hickinbottom, JCS 113, 993(1918)... 

---