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Revision as of 16:19, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,044 edits Saving copy of the {{chembox}} taken from revid 469565256 of page Ethyl_methanesulfonate for the Chem/Drugbox validation project (updated: 'KEGG').		Latest revision as of 17:27, 11 January 2025 edit AnomieBOT (talk | contribs)Bots6,582,806 editsm Dating maintenance tags: {{Cn}}
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{Chembox		{{Chembox
	| Verifiedfields = changed		|Verifiedfields = changed
	| Watchedfields = changed		|Watchedfields = changed
	| verifiedrevid = 415323682		|verifiedrevid = 470455885
	| Reference = <ref>'']'', 11th Edition, '''3782'''.</ref>		|Reference = <ref>'']'', 11th Edition, '''3782'''.</ref>
	| ImageFile_Ref = {{chemboximage|correct|??}}		|ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageFile = Ethyl-mesylate-2D-skeletal.svg		|ImageFile = Ethyl-mesylate-2D-skeletal.svg
	| ImageSize = 180px		|ImageSize = 180px
	| ImageName = Skeletal formula		|ImageName = Skeletal formula
	| ImageFile1 = Ethyl-mesylate-3D-balls.png		|ImageFile1 = Ethyl-mesylate-3D-balls.png
			|ImageName1 = Ball-and-stick model
	| ImageSize1 =
			|PIN = Ethyl methanesulfonate
	| ImageName1 = Ball-and-stick model
			|OtherNames = Ethyl mesylate<br>Ethyl methanesulphonate
	| IUPACName = 1-Methylsulfonyloxyethane
			|Section1={{Chembox Identifiers
	| OtherNames = Ethyl mesylate<br>Ethyl methanesulphonate
			|Abbreviations = EMS
	| Section1 = {{Chembox Identifiers
			|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| Abbreviations = EMS
			|ChemSpiderID = 5887
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|InChIKey = PLUBXMRUUVWRLT-UHFFFAOYAM
	| ChemSpiderID = 5887
			|ChEBI_Ref = {{ebicite|correct|EBI}}
	| InChIKey = PLUBXMRUUVWRLT-UHFFFAOYAM
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		|ChEBI = 23994
			|ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 338686		|ChEMBL = 338686
			|EC_number = 200-536-7
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3
			|StdInChI = 1S/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = PLUBXMRUUVWRLT-UHFFFAOYSA-N
			|StdInChIKey = PLUBXMRUUVWRLT-UHFFFAOYSA-N
	| CASNo = 62-50-0
	| CASNo_Ref = {{cascite|correct|CAS}}		|CASNo = 62-50-0
			|CASNo_Ref = {{cascite|correct|CAS}}
			|UNII_Ref = {{fdacite|correct|FDA}}
	| EINECS =
			|UNII = 9H154DI0UP
	| PubChem = 6113
	| SMILES = O=S(=O)(OCC)C		|PubChem = 6113
			|SMILES = O=S(=O)(OCC)C
	| InChI = 1/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3		|InChI = 1/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3
			|KEGG_Ref = {{keggcite|correct|kegg}}
	| RTECS =
			|KEGG = C19239
	| MeSHName =
	| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI =
	| KEGG_Ref = {{keggcite|changed|kegg}}
	| KEGG = <!-- blanked - oldvalue: C19239 -->
	| ATCCode_prefix =
	| ATCCode_suffix =
	| ATC_Supplemental =}}
	| Section2 = {{Chembox Properties
	| Formula = CH<sub>3</sub>SO<sub>3</sub>C<sub>2</sub>H<sub>5</sub>
	| MolarMass =124.16 g/mol
	| Appearance = Clear colorless liquid
	| Density = 1.1452 g/cm<sup>3</sup> (22 °C)
	| MeltingPt = < 25 °C
	| Melting_notes =
	| BoilingPt = 213–213.5 °C, 486.2-486.7 K
	| Boiling_notes =
	| Solubility =
	| SolubleOther =
	| Solvent =
	| pKa =
	| pKb = }}
	| Section7 = {{Chembox Hazards
	| EUClass =
	| EUIndex =
	| MainHazards =
	| NFPA-H = 1
	| NFPA-F = 1
	| NFPA-R = 0
	| NFPA-O =
	| RPhrases =
	| SPhrases =
	| RSPhrases =
	| FlashPt =
	| Autoignition =
	| ExploLimits =
	| PEL = }}
	}}		}}
			|Section2={{Chembox Properties
			|Formula = CH<sub>3</sub>SO<sub>3</sub>C<sub>2</sub>H<sub>5</sub>
			|MolarMass =124.16 g/mol
			|Appearance = Clear colorless liquid
			|Density = 1.1452 g/cm<sup>3</sup> (22 °C)
			|MeltingPt = < 25 °C
			|BoilingPtC = 85-86
			|BoilingPt_notes = /10 mmHg(lit)
			|VaporPressure = 0.044 kPa @ 25˚C<ref>{{Cite web |title=Ethyl Methanesulfonate |url=https://ntp.niehs.nih.gov/ntp/roc/content/profiles/ethylmethanesulfonate.pdf |access-date=18 June 2021 |website=Report on Carcinogens, Fourteenth Edition |publisher=NIEHS}}</ref>
			}}
			|Section3={{Chembox Hazards
			| GHS_ref=<ref>{{Cite web |title=Ethyl methanesulfonate |url=https://pubchem.ncbi.nlm.nih.gov/compound/6113#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
			| GHSPictograms = {{GHS07}}{{GHS08}}
			| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|302|340|351}}
			| PPhrases = {{P-phrases|203|264|270|280|301+317|318|330|405|501}}
			|NFPA-H = 1
			|NFPA-F = 1
			|NFPA-R = 0
			}}
			}}
			'''Ethyl methanesulfonate''' ('''EMS''') is an ] with the formula {{chem2|CH3SO3C2H5}}. It is the ethyl ester of ]. A colorless liquid, it is classified as an ]. EMS is the most commonly used chemical mutagen in experimental ].<ref>{{Cite journal |last=Kutscher |first=Lena M. |last2=Shaham |first2=Shai |year=2014 |title=Forward and reverse mutagenesis in C. elegans |url=http://www.wormbook.org/chapters/www_frmutagenesis/frmutagenesis.html |journal=WormBook: The Online Review of C. Elegans Biology |publisher=WormBook |pages=1–26 |doi=10.1895/wormbook.1.167.1 |pmc=4078664 |pmid=24449699 |access-date=18 June 2021}}</ref><ref name="Sega 1984 pp. 113–142">{{Cite journal |last=Sega |first=Gary A. |year=1984 |title=A review of the genetic effects of ethyl methanesulfonate |journal=Mutation Research/Reviews in Genetic Toxicology |publisher=Elsevier BV |volume=134 |issue=2–3 |pages=113–142 |doi=10.1016/0165-1110(84)90007-1 |issn=0165-1110 |pmid=6390190}}</ref> Mutations induced by EMS exposure can then be studied in ]s or other assays.
			== Use in biological research ==
			EMS produces random ]s in genetic material by ] substitution; particularly through G:C to A:T ] induced by ] ]. EMS typically produces only ]s. Due to its potency and well understood mutational spectrum,{{cn|date=January 2025}}
			EMS can induce mutations at a rate of 5x10<sup>−4</sup> to 5x10<sup>−2</sup> per gene without substantial killing. A 5x10<sup>−4</sup> per gene mutation rate observed in a typical EMS mutagenesis experiment of the model organism '']'', corresponds to a raw mutation rate of ~7x10<sup>−6</sup> mutations per G/C base pair, or about 250 mutations within an originally mutagenized gamete (containing a ~100 Mbp, 36% ] haploid genome).<ref name="Anderson1995">{{Cite book |last=Anderson |first=Philip |title=Caenorhabditis elegans: Modern Biological Analysis of an Organism |publisher=Elsevier |year=1995 |isbn=978-0-12-564149-4 |series=Methods in Cell Biology |volume=48 |pages=31–58 |chapter=Chapter 2 Mutagenesis |doi=10.1016/s0091-679x(08)61382-5 |issn=0091-679X}}</ref> Such a mutagenized gamete would have about 9 different ] mutations in genes, with 1 to 2 of these mutations being within essential genes and therefore lethal. However, since it is unlikely the same essential gene is mutated in independent gametes, and if loss of the essential gene did not kill the gamete itself, downstream gamete fusion often allows for survival of the resulting zygote and organism, as the now ] non-functional mutated ] may be rescued by the still ] allele provided by the other gamete.<ref name="Anderson1995" />
			== Mechanism of mutagenesis ==
			The ] of EMS reacts with guanine in ], forming the abnormal base ''O''<sup>6</sup>-ethylguanine. During ], DNA polymerases that ] the process frequently place thymine, instead of cytosine, opposite ''O''<sup>6</sup>-ethylguanine. Following subsequent rounds of replication, the original G:C ] can become an A:T pair (a ] mutation). This changes the genetic information, is often harmful to cells, and can result in ]. RNA polymerase can also place ] (RNA analog of thymine) opposite an ''O''<sup>6</sup>-ethylguanine lesion.<ref name="Gerchman Ludlum 1973 pp. 310–316">{{Cite journal |last=Gerchman |first=Lois L. |last2=Ludlum |first2=David B. |year=1973 |title=The properties of in templates for RNA polymerase |journal=Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis |publisher=Elsevier BV |volume=308 |issue=2 |pages=310–316 |doi=10.1016/0005-2787(73)90160-3 |issn=0005-2787 |pmid=4706005}}</ref>
			== Repair of mutagenic lesion ==
			''O''<sup>6</sup>-ethylguanine can be repaired '']'' in a stoichiometric fashion by reacting with the active site cysteine of the ] repair protein.<ref name="Pegg 2000 pp. 83–100">{{Cite journal |last=Pegg |first=Anthony E |year=2000 |title=Repair of O6-alkylguanine by alkyltransferases |journal=Mutation Research/Reviews in Mutation Research |publisher=Elsevier BV |volume=462 |issue=2–3 |pages=83–100 |doi=10.1016/s1383-5742(00)00017-x |issn=1383-5742 |pmid=10767620}}</ref> The ''in vivo'' half-life of ''O''<sup>6</sup>-ethylguanine was reported to be about 9 days in mouse brain, while it was about 1 day in mouse liver.<ref name="Goth Rajewsky pp. 639–643">{{Cite journal |last=Goth |first=R. |last2=Rajewsky |first2=M. F. |date=1974-03-01 |title=Persistence of O6-Ethylguanine in Rat-Brain DNA: Correlation with Nervous System-Specific Carcinogenesis by Ethylnitrosourea |journal=Proceedings of the National Academy of Sciences |volume=71 |issue=3 |pages=639–643 |bibcode=1974PNAS...71..639G |doi=10.1073/pnas.71.3.639 |issn=0027-8424 |pmc=388067 |pmid=4522778 |doi-access=free}}</ref>
			==Induction of recombination==
			EMS induces ] ] in '']''.<ref name="Yost1967">{{Cite journal |last=Yost Jr |first=H. T. |last2=Chaleff |first2=R. S. |last3=Finerty |first3=J. P. |date=1967 |title=Induction of mitotic recombination in Saccharomyces cerevisiae by ethyl methane sulphonate |journal=Nature |volume=215 |issue=5101 |pages=660–661 |bibcode=1967Natur.215..660Y |doi=10.1038/215660a0 |pmid=6050236 |s2cid=1982778}}</ref> It was suggested that EMS ] may result in a ] leading to genetic exchange.<ref name = Yost1967/>
			] ]s defective in any one of six ]s known to be required for ] were found to be more sensitive to inactivation by EMS than wild type bacteriophage.<ref name="Johns1978">{{Cite journal |last=Johns |first=V. |last2=Bernstein |first2=C. |last3=Bernstein |first3=H. |date=1978 |title=Recombinational repair of alkylation lesions in phage T4. II. Ethyl methanesulfonate |journal=Molecular & General Genetics |volume=167 |issue=2 |pages=197–207 |doi=10.1007/BF00266913 |pmid=215891 |s2cid=30597383}}</ref> This finding suggests that a recombination process catalyzed by the proteins specified by these six genes is employed in repairing EMS lethal lesions in DNA.<ref name = Johns1978/>
			== Stability ==
			Generally speaking EMS is unstable in water. It hydrolyzes to ethanol and methanesulfonic acid. At neutral to acidic pH at room temperature, it has a fairly long ] of over 1 day.<ref name="FROESE-GERTZEN KONZAK FOSTER NILAN 1963 pp. 447–448">{{Cite journal |last=FROESE-GERTZEN |first=EDITH E. |last2=KONZAK |first2=C. F. |last3=FOSTER |first3=R. |last4=NILAN |first4=R. A. |year=1963 |title=Correlation between Some Chemical and Biological Reactions of Ethyl Methanesulphonate |journal=Nature |publisher=Springer Science and Business Media LLC |volume=198 |issue=4879 |pages=447–448 |bibcode=1963Natur.198..447F |doi=10.1038/198447a0 |issn=0028-0836 |s2cid=12359460}}</ref><ref name="Afza2003">{{Cite book |last=Kodym |first=Andrea |title=Plant functional genomics |last2=Afza |first2=Rownak |publisher=Humana Press |year=2003 |isbn=978-1-58829-145-5 |publication-place=Totowa, N.J |pages=189–203 |chapter=Chapter 12 Physical and Chemical Mutagenesis |oclc=51445955}}</ref> Therefore, EMS must be specifically degraded before disposal. Protocols call for degradation of EMS in an equal volume of a 0.1M ] and 20% w/v ] "inactivating solution", for at least six half-lives (>24 hours).<ref name="Anderson1995" /> The half-life of EMS in 1M NaOH is 6 hours at room temperature, while in a 10% w/v sodium thiosulfate solution it has a half-life of 1.4 hours.<ref name="Afza2003" />
			==Safety==
			EMS is ]ic, ]ic, and ]ic {{cn|date=January 2025}}
			==See also==
			* ]
			* ]
			* ]
			* ]
			== References ==
			{{Reflist}}
			]
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