Ethyl Methanesulfonate

A mixture of 2.3 parts of 2-(4-methoxyphenyl)ethyl methanesulfonate, 4.9 parts of 1-[(4-fluorophenyOmethyl] -N-(4-piperidinyl)-1H-benzimidazol-2-amine dihydrobromide, 3.2 parts of sodium carbonate, 0.1 part of potassium iodide and 90 parts of N,N-dimethylformamide is stirred overnight at 70°C. The reaction mixture is poured onto water. The product is extracted with methylbenzene. The extract is washed with water,dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloro-methane and methanol (98 2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2,2 -oxybispropane, yielding 2.2 parts (48%) of 1 -(4-fluorophenvlmethyl)-N-[1 - [2-(4-methoxvphenyl)ethvl] -4-piperidinyl] -1H-benzlmidazol-2-amine MP 149.1°C. 

Clark, M.W., R.P. Gildersleeve, J.P. Thaxton, C.R. Parkhurst, and D.I. McRee. 1988. Hematological effects of ethyl methanesulfonate, paraquat and phenylhydrazine in Japanese quail. Comp. Biochem. Physiol. 89C 15-30. 

H. G. Ramjit, M. M. Singh and A. B. Coddington, Gas chromatographic/mass spectro-metric analysis of methyl methanesulfonate and ethyl methanesulfonate in the bismesy-late salt of DPI 201-106, a positive inotropic agent for the treatment of heart failure. Journal of Mass Spectrometry, 31(8), 867-872.1996. 

W. Li, Trace analysis of residual methyl methanesulfonate, ethyl methanesulfonate and isopropyl methanesulfonate in pharmaceuticals by capillary gas chromatography with flame ionization detection. Journal of Chromatography A, 2004,1046(1-2), 297-301. 

Ethylene sulfide Ethylene thiourea 2-Ethylhexyl aerylate Ethyl methanesulfonate A-Ethyl-A-nitrosourea... 

Shaw, E.I. and Hsie, A.W. (1978). "Conditions necessary for quantifying ethyl methanesulfonate-induced mutations to pmine-analogue resistance in Chinese hamster V79 cells, Mutat. Res. 51, 237. 

Katoh M, Cacheiro NLA, Cornett CV, Cain KT, Rutledge JC, Generoso WM (1989) Fetal anomalies produced subsequent to treatment of zygotes with ethylene oxide or ethyl methanesulfonate are not likely due to the unusual genetic causes. Mutat Res, 210 337-344. 

Teaf, C.M., Bishop, J.B. Harbison, R.D. (1990) Potentiation of ethyl methanesulfonate induced germ cell mutagenesis and depression of glutathione in male reproductive tissues by 1,2-dibromoethane. Teratog. Carcinog. Mutag., 10, 427-438... 

Klungland, A., Laake, K., Hoff, E. Secbcrg, E. (1995) Spectrum of mutations induced by methyl and ethyl methanesulfonate at the hprt locus of nonnal and tag expressing Chinese hamster fibroblasts. Carcinogenesis, 16, 1281-1285... 

Effect of glabrene against ethyl methanesulfonate-induced revertants in E. coli JC5088 (rec- strain). 

One example does exist where the effects of ortho methyl groups are essentially additive. With ethyl methanesulfonate in water as the quatemizing agent, one methyl substituent suppresses reactivity by a factor of 2, the second by only 4.3. Moreover, the reaction is unusual in... 

Jacobs, M., Dolferus, R. Van Den Bossche, D. (1988). Isolation and biochemical analysis of ethyl methanesulfonate-induced alcohol dehydrogenase null mutants of Arabidopsis thaliana (L.) Heynh. Biochemical Genetics 26,105-22. 

When typhimurium was incubated with chemical mutagens such as N-methyl-N -nitro-N-nitrosoguanidine, nitrofurazone, methyl me-thanesulfonate, and ethyl methanesulfonate, for 10 h the current decrease of the electrode was measured. The response of the electrode increased with increasing concentration of chemical mutagens. Therefore, the mutagenicity of chemicals can be estimated with the microbial electrode. 

Ethinyloestradiol Ethyl acrylate Ethylene dibromide (EDB) Ethylene dichloride (EDC) Ethyleinimine Ethylene oxide Ethylene thiourea Ethyl methanesulfonate /V-Ethyl-/V-nitrosourea Formaldehyde 2-(2-Furyl)-3-(5-nitro-2-furyl) acrylamide... 

Wear protective gloves, laboratory coat, goggles, and breathing apparatus if necessary. Cover spill with a 1 1 1 mixture by weight of soda ash, clay cat litter (bentonite), and sand. Scoop the mixture into a plastic container and either label and send for disposal by burning,4 6 or, in the fume hood, add the mixture to a solution of potassium hydroxide in ethanol allowing 0.12 mol (7.9 g) of 85% potassium hydroxide pellets and 32 mL of ethanol for each 0.1 mol (12.4 g) of ethyl methanesulfonate to be destroyed. Heat the mixture under reflux for 8 hours. Decant the cooled solution into the drain with water. Treat the solid as normal refuse.6... 

Small Quantities. Wear protective clothing, gloves, and goggles. Work in the fume hood. Place 7.9 g (0.12 mol) of 85% potassium hydroxide pellets in a 100-mL, threenecked, round-bottom flask equipped with a stirrer, condenser, and dropping funnel. Add 32 mL of ethanol rapidly. Heat the solution to gentle reflux and add ethyl methanesulfonate (12.4 g, 0.1 mol) at such a rate to maintain gentle reflux. Heat under reflux while stirring for 2 hours. Cool, dilute the reaction mixture with water, and wash into the drain with water.7... 

Another problem is the impact of "mild" mutations— those which produce only small effects, which arise at relatively high rates, and which are inefficiently selected out of populations. Although it is currently virtually impossible to detect such effects clinically in humans, it is clear that they contribute markedly to the total mutational load in Drosophila, where they outnumber "severe" (recessive lethal and semilethal) mutations by a factor of at least 10 and significantly reduce the health of the typical wild fly. The same is true for mutations induced by ethyl methanesulfonate, but other chemicals have not been tested. 

Diepoxybutane M-Methyl-4-aminoaaobenzene Di-n-butylnitrosamine 2-Nitrosonaphthalene Ethyl methanesulfonate 5-Nitro-2-furoic acid Isophosphamide 4-Aminoaxobensene Melphalan... 

ADDUCT A chemical addition product. For example, when the mutagenic alkylating agent ethyl methanesulfonate reacts with DNA, any of the normal bases in DNA (i.e., adenine, thymine, guanine, and cytosine) may be converted into adducts, such as N7-ethylguanine and N3-ethylcytosine. 

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