1 -Methyl-3-nitro-1 -nitrosourea

A comparison of structures of V-methyl-V-nitroso-p-nitrobenzamide, N,N -dimethyl-V-nitrosourea, V-methyl-V-nitrosourea, 2-nitroso-2-azabicyclo[2.2.2]octan-3-one to those of V-methyl-V -nitro-V-nitrosoguanidine and V,V -dimethyl-V"-cyano-V-nitrosoguanidine shows that the N—N and C—NNO bond lengths in the nitroguanidines44 are similar to those found in the nitrosoamides, but that the corresponding bonds in... 

AOM, azoxymethane MNNG, JV-methyl-JV -nitro-JV-mtrosoguamdine DMH, 1,2-dimethyl-hydrazine MNU, W-methyl-W-nitrosourea PhIP, 2-amino-l-methyl-6-phenylimidazole[4,5-b] pyridine sc, subcutaneous ip, intra-peritoneal ir, intra-rectal po, by mouth. 

Major sources are the basic hydrolysis of V-methyl-V-nitrosourea (or V-methyl-V-nitroso-/)-toluenesulfonamide (Diazald ) or l-methyl-3-nitro-l-nitrosoguanidine (MNNG). 

Ethyl A-methyl-A-nitrosocarbamate, 1597 Lead(II) trinitrosobenzene-1,3,5-trioxide, 3594 l-Methyl-3-nitro-l-nitrosoguanidine, 0876 A-Methyl-A-nitrosourea, 0875... 

Tatematsu, M. et al.. Induction of glandular stomach cancers in Helicobacter pylori-sensitive Mongolian gerbils treated with N-methyl-N-nitrosourea and N-methyl-N-nitro-N-nitrosoguanidine in drinking water, Jpn. J. Cancer Res., 89, 97, 1998. 

Methylenedianiline dihydrochloride Methyl methanesidfonate JV-Methyl-iV -nitro-iV-nitrosoguanidine JV-Methyl-iV-nitrosourea Methyloxirane... 

MethylenedianiUne dihydrochloride Methyl methanesulfonate N-Methyl-AT -nitro-Af-nitrosoguanidine N-Methyl-Af-nitrosourea Methyloxirane... 

Analysis of Reagent Purity diazomethane is titrated by adding a known quantity of benzoic acid to an aliquot of the solution such that the solution is colorless and excess benzoic acid remains. Water is then added, and the amount of benzoic acid remaining is back-titrated with NaOH solution. The difference between the amount of acid added and the amount remaining reveals the amount of active diazomethane present in the aliquot. Preparative Methods diazomethane is usually prepared by the decomposition of various derivatives of IV-methyl-IV-nitrosoamines. Numerous methods of preparation have been described, but the most common and most frequently employed are those which utilize N-Methyl-N-nitroso-p-toluenesulfonamide (Diazald 1), l-Methyl-3-nitro-l-nitrosoguanidine (MNNG, 2), or N-methyl-N-nitrosourea (3). ... 

Gichner, T. Veleminsky, J. (1987) The organic solvents acetone, ethanol and dimethylformamide potentiate the mutagenic activity of V-methyl-V -nitro-V-nitrosoguanidine, but have no effect on the mutagenic potential of -mcthyl- -nitrosourea. Mutat. Res., 192, 31-35... 

Diazoethane and higher diazo-compounds may be used in much the same way as diazomethane. Diazoethane can be made from N-nitrosourea [54] or N-ethyl-3-nitro-N-nitrosoguanidine [58] using the same apparatus [49, 52]. There is not a great deal to choose between methyl and ethyl esters made this way, but the following example indicates one rationale for making the distinction. 

Treatment for two complete cell cycles with increasing SAB concentrations significantly elevated the SCE frequency in CHO cells (Fig. 2a). Exposure to the alkylating agents MMS (10" M), ethyl nitrosourea (ENU, 10" Af), ethyl methanesulfonate (EMS, 10"" M), or N-methyl-N -nitro-N-nitrosoguanidine (MNNG, 10" M), in combination with SAB resulted in synergistic increases in SCEs (Fig. 2b). 

Irradiation and Alkylation Conditions. X-ray doses of 3-6 Gy were delivered from a Phillip s RTIOO X-ray machine (200 kVp 15 mA with a nominal half value layer of 0.35 cm copper). Cultures were inadiated with an incident dose rate of 1.3 J m s UV light (254 nm). Cultures were exposed to various concentrations of N-methyl-N -nitro-N-nitrosoguanidine (MNNG) (Aldrich Chemical Co., Milwaukee, Wl), MMS (ICN Pharmaceuticals, Hainview, NY), ethyl methanesulfonate(EMS) (ICN Pharmaceuticals), or ethyl nitrosourea (ENU) (a gift of B. Singer, University of California, Berkeley), in tissue culture medium for 60 min to 4 h. 

Nduka N, Skodmore CJ, Shall S (1980) The enhancement of cytotoxicity of N-methyl-N -Nitro-N-nitrosourea and of 7-irradiation by inhibitors of poly(ADP-ribose) polymerase. Eur J Biochem 105 525-530... 

W-Ethyl-M-nitrosourea was decomposed faster with increasing concentrations of Cu (2.5-40 pmol/l) at pH 6 and 37 C in a concentration-dependent manner (Preussmann et al. 1975). Acceleration by NF was markedly weaker. In the presence of Cu the half life of M-methyl-N -nitro-hJ-nitrosoguanidin was only 39 min instead of 35 h. There was a linear relationship between the rate of degradation and the concentration of Cu or Ni ions. The metal ions enter the reaction in stoichiometric amounts. The elevation of the rate of decomposition completely agreed with the findings of Zeller and Ivankovich (1972) and Ivankovich etal. (1972) who observed an enhancement of the acute toxicity and the carcinogenicity of W-ethyl-W-nitrosourea administered simultaneously with CUSO4 or NiSO. ... 

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