Methyl methanesulfonate (MMS), also known as methyl mesylate, is an alkylating agent and a carcinogen. It is also a suspected reproductive toxicant, and may also be a skin/sense organ toxicant.[1] It is used in cancer treatment.[2]
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Names | |||
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Preferred IUPAC name
Methyl methanesulfonate | |||
Other names
Methanesulfonic acid methyl ester
Methyl mesylate MMS | |||
Identifiers | |||
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3D model (JSmol)
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ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.000.568 | ||
EC Number |
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KEGG |
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MeSH | D008741 | ||
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |||
C2H6O3S | |||
Molar mass | 110.13 g/mol | ||
Density | 1.3 g/mL at 25 °C | ||
Boiling point | 202 to 203 °C (396 to 397 °F; 475 to 476 K) | ||
Related compounds | |||
Related compounds
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Ethyl methanesulfonate, dimethyl sulfone, dimethyl sulfate | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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MMS methylates DNA predominantly on N7-deoxyguanosine and N3-deoxyadenosine, and to a much lesser extent also methylates at other oxygen and nitrogen atoms in DNA bases, and also methylates one of the non-carbon bound oxygen atoms of the phosphodiester linkage. Originally, this action was believed to directly cause double-stranded DNA breaks, because homologous recombination-deficient cells are particularly vulnerable to the effects of MMS.[3] However, it is now believed that MMS stalls replication forks, and cells that are homologous recombination-deficient have difficulty repairing the damaged replication forks.[3]