Methyl methanesulfonate

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]

Methyl methanesulfonate

Skeletal formula Ball-and-stick model
Names
Preferred IUPAC name Methyl methanesulfonate
Other names Methanesulfonic acid methyl ester Methyl mesylate MMS
Identifiers
CAS Number	66-27-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:25255
ChemSpider	4013
ECHA InfoCard	100.000.568
EC Number	200-625-0
KEGG	C19181
MeSH	D008741
PubChem CID	4156
UNII	AT5C31J09G
CompTox Dashboard (EPA)	DTXSID7020845
InChI InChI=1S/C2H6O3S/c1-5-6(2,3)4/h1-2H3 Key: MBABOKRGFJTBAE-UHFFFAOYSA-N InChI=1/C2H6O3S/c1-5-6(2,3)4/h1-2H3 Key: MBABOKRGFJTBAE-UHFFFAOYAK
SMILES COS(=O)(=O)C
Properties
Chemical formula	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	Ethyl methanesulfonate
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

Chemical reactions with DNA

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 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]

See also

Dimethyl sulfite, a chemical with the same molecular formula but different arrangement

References

1. Scorecard Pollution Information Site: Methyl Methanesulfonate Scorecard.org Accessed 14 Feb 08
2. Medical.Webends.com: Methyl Methanesulfonate Archived 2008-02-15 at the Wayback Machine Medical.webends.com Accessed 14 Feb 08
3. Lundin C, North M, Erixon K, Walters K, Jenssen D, Goldman AS, Helleday T (2005). "Methyl methanesulfonate (MMS) produces heat-labile DNA damage but no detectable in vivo DNA double-strand breaks". Nucleic Acids Research. 33 (12): 3799–3811. doi:10.1093/nar/gki681. PMC 1174933. PMID 16009812.