Ethyl methanesulfonate

Description

Ethyl methanesulfonate (EMS), also called ethyl mesylate, is a simple, but hazardous, sulfonic acid ester. Its earliest preparation, reported by German organic chemist O. C. Billeter in 1905, was the reaction of methanesulfonic anhydride with ethyl alcohol.
As shown in the hazard information table, EMS is suspected of being mutagenic, teratogenic, and carcinogenic. In an early mutagenicity study (1965), Thomas Alderson at the University of Cambridge (UK) used EMS to induce mutations in fruit flies (Drosophila spp.).
In 1984, Gary A. Sega at Oak Ridge National Laboratory (TN) published an extensive review of EMS’s genetic effects. And last year, in its 15th Report on Carcinogens, the National Toxicology Program (NTP) of the US Department of Health and Human Services included a data sheet on the carcinogenicity of EMS. In addition, NTP also reported a summary of the testing status of the compound.
Because of its extreme toxicity, EMS is produced only for research purposes. Its primary use is as a model alkylating agent in biochemical and medical research, specifically in studies of DNA repair processes.

Chemical properties

colourless liquid

Chemical properties

Ethyl methane sulfonate is a clear liquid.

The Uses of Ethyl methanesulfonate

Ethyl methanesulfonate is used as mutagen for both mammalian and plant cells. It finds application as a model alkylating agent in the study of deoxyribonucleic acid (DNA) repair processes.

The Uses of Ethyl methanesulfonate

Experimentally as mutagen, teratogen and brain carcinogen.

What are the applications of Application

Ethyl methanesulfonate is a DNA ethylating mutagenic agent

Definition

ChEBI: A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.

General Description

Clear colorless liquid. Denser than water.

Air & Water Reactions

Water soluble.

Reactivity Profile

Ethyl methanesulfonate alkylates nucleophiles such as hydroxy, amino and sulfhydryl groups in model and biological materials. Is hydrolyzed by excess aqueous alkali to non-corrosive and non-toxic products. Is hydrolyzed by water to a highly corrosive product .

Fire Hazard

Ethyl methanesulfonate is combustible.

Biochem/physiol Actions

Ethyl methanesulfonate is a DNA ethylating agent, mutagenic to plants and animals and carcinogenic in mammals. It has been used as a model alkylating agent in studies of DNA repair processes. EMS induces base substitutions of guanine-cytosine (G/C) to adenine-thymine (A/T). EMS also generates point mutations and single nucleotide polymorphisms in genomes. EMS is potential chemical mutagen used for inducing mutation in rice, wheat and Arabidopsis thaliana.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplas tigenic, tumorigenic, and teratogenic data. Poison by ingestion and intraperitoneal routes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of SOx. See also SULFONATES and ESTERS.

Potential Exposure

Used as a research tool for mutagenesis and carcinogenesis studies. Was considered as a possible human male contraceptive. Also considered as a reversible male hemosterilant for insects and mammalian pests.

Carcinogenicity

Ethyl methanesulfonate is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. Military driver shall be given full and complete information regarding shipment and conditions in case of emergency. AR 50-6 deals specifically with the shipment of chemical agents. Shipments of agent will be escorted in accordance with AR 740-32.

Incompatibilities

Vapors may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides. Contact with moisture may cause hydrolysis or other forms of decomposition