Absorption, Distribution and Excretion
…It distributes rapidly in mammals and increases the excretion of methylnicotinamide. Metabolism/Metabolites …Metabolic pathways include reaction with glutathione to form ethyl mercaptouric acid, and hydrolysis to form ethanol. Biological Half-Life …The half-life in rat serum is 6.5 hours.

Interactions
This study investigated the antimutagenic effects of vitamins C, E, and A, and their derivatives, on 6TG resistance mutations induced by ethyl methanesulfonate in Chinese hamster V79 cells. Vitamin C was most effective in inhibiting the cytotoxicity of ethyl methanesulfonate and 6TG resistance mutations. In the presence of 100 μg/ml vitamin C, the mutation rate induced by ethyl methanesulfonate was reduced to approximately one-third or one-quarter of that in the control group (treated with ethyl methanesulfonate only). Dehydrovitamin C and isovitamin C also inhibited ethyl methanesulfonate-induced mutations, reducing them to approximately one-half or one-third of those in the control group. …Vitamin C may act as a demutant, reacting directly with ethyl methanesulfonate, thereby inactivating its mutagenic activity in Chinese hamster V79 cells. Vitamin E exhibited additive cytotoxicity against EMS-induced cytotoxicity. This vitamin enhanced the frequency of 6TG resistance mutations induced by ethyl methanesulfonate. Pretreatment with vitamin E prior to ethyl methanesulfonate treatment had no detectable effect on ethyl methanesulfonate-induced mutations. Conversely, vitamin A significantly enhanced the mutation frequency induced by ethyl methanesulfonate. The antimutagenic effect of the 1,4-dihydropyridine derivative 2,6-dimethyl-3,5-diethoxycarbonyl-4-(sodium carboxylate)-1,4-dihydropyridine in dominant and sex-linked recessive lethal assays in Drosophila was investigated. …1,4-Dihydropyridine reduced the frequency of genetic damage (point mutations and chromosome breaks) induced by ethyl methanesulfonate. In adults pretreated with 1,4-dihydropyridine, a reduced mutation rate induced by ethyl methanesulfonate was observed regardless of developmental stage (larva or adult). The protective effect of this antimutagenic agent against alkylating agents depended on the dosage of 1,4-dihydropyridine and the level of mutation rate induced by ethyl methanesulfonate. The effect of 1,4-dihydropyridine was more significant than that of cysteine and cysteamine.
Rat and canine hepatocyte suspensions were exposed to toxic concentrations of ethyl methanesulfonate (EMS) and ionophore A-23187, with or without extracellular calcium ions (Ca2+) and α-tocopherol succinate (α-TS). Exogenous administration of α-tocopherol synthase (α-TS, 25 μM) completely protected hepatocytes from chemically induced toxicity, even when exposed to physiological concentrations of free extracellular calcium ions (0.8–1.5 mM). However, hepatocytes exposed to non-esterified α-tocopherol (α-T, 25 μM) or α-tocopherol acetate (α-TA, 25 μM) were not protected from the toxic effects of the chemicals, although these treatments resulted in significant intracellular accumulation of α-T (2.65 nmol/10⁶ cells) and α-TA (2.3 nmol/10⁶ cells), respectively. The results indicate that supplementation with endogenous α-T or α-TA does not enhance protection against chemical toxicity. The cytoprotective effect of α-TS does not stem from the accumulation of α-T, but rather from the presence of intact α-TS molecules within the cell. Therefore, α-TS appears to possess cytoprotective properties distinct from other vitamin E homologues. EMS, when used in combination with chlortetracycline, exhibits high cytotoxicity, but EMS alone inhibits mitosis in broad beans. For more complete data on interactions of ethyl methanesulfonates (7 in total), please visit the HSDB record page. Non-human toxicity values: Oral LD50 in mice: 470 mg/kg

According to an independent committee of scientific and health experts, ethyl methanesulfonate may be carcinogenic. Ethyl methanesulfonate is a clear, colorless liquid with a density greater than water. (NTP, 1992) Ethyl methanesulfonate is a methanesulfonate ester formed by the condensation of methanesulfonic acid and ethanol. It possesses various activities including alkylating agent, antitumor agent, carcinogen, genotoxin, mutagen, and teratogen. There are reports on ethyl methanesulfonate in Arabidopsis thaliana, and relevant data are available. Ethyl methanesulfonate is a sulfonoxyalkane with carcinogenic and teratogenic properties. Ethyl methanesulfonate can ethylate DNA, thereby damaging DNA and leading to gene mutations, DNA single-strand breaks, and chromosomal aberrations. Ethyl methanesulfonate can be used for experimental purposes in biomedical research. (NCI04) An antitumor drug with alkylating properties. It can also act as a mutagen by damaging DNA and has been used in experimental studies to investigate this effect.

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Mechanism of Action
/Genetoxicity/ By comparing two ethylating agents, the relative importance of different alkylation sites on DNA was determined. In the ethylation of DNA by 1-ethyl-1-nitrosourea, the total adduct proportion at the epoxide was higher than that of ethyl methanesulfonate, while in the ethylation of guanine at the N-7 position by ethyl methanesulfonate, the total adduct proportion was even higher. To determine the importance of the guanine O6-G site relative to the N-7 site in germline mutagenesis, we constructed dose-response curves for 1-ethyl-1-nitrosourea and ethyl methanesulfonate. Dosage was measured by the total number of adducts per deoxynucleotide, and response was measured by the number of sex-linked recessive lethal mutations induced in Drosophila sperm. The dose-response curves for both mutagens were linear and extrapolated to the origin. …The efficiency of 1-ethyl-1-nitrosourea in inducing sex-linked recessive lethal mutations was 1.9 times that of ethyl methanesulfonate (per adduct). In vitro studies showed that 1-ethyl-1-nitrosourea induced adducts at the O6-G site accounted for 9.5% of its total adducts, while ethyl methanesulfonate accounted for only 2.0%. If O6-G were the only genotoxic site, the addition efficiency of 1-ethyl-1-nitrosourea would be 4.8 times that of ethyl methanesulfonate. …Although O6-G is the major genotoxic site, N-7-G also contributes significantly to germline mutations.

C3H8O3S

124.15

124.019

62-50-0

Ethyl methanesulfonate-d5;1219795-44-4

6113

Colorless to light yellow liquid

1.2±0.1 g/cm3

214.4±9.0 °C at 760 mmHg

< 25ºC

100.0±0.0 °C

0.2±0.4 mmHg at 25°C

1.416

-0.03

0

3

2

7

118

0

S(C([H])([H])[H])(=O)(=O)OC([H])([H])C([H])([H])[H]

PLUBXMRUUVWRLT-UHFFFAOYSA-N

InChI=1S/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3

ethyl methanesulfonate

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO: ≥ 100 mg/mL (805.48 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (20.14 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (20.14 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (20.14 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)