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
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
Methyl methanesulfonate
Other names
Methanesulfonic acid methyl ester
Methyl mesylate
MMS
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.568
EC Number
  • 200-625-0
KEGG
MeSH D008741
UNII
  • InChI=1S/C2H6O3S/c1-5-6(2,3)4/h1-2H3 ☒N
    Key: MBABOKRGFJTBAE-UHFFFAOYSA-N ☒N
  • InChI=1/C2H6O3S/c1-5-6(2,3)4/h1-2H3
    Key: MBABOKRGFJTBAE-UHFFFAOYAK
  • COS(=O)(=O)C
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
 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).
☒N verify (what is checkY☒N ?)
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 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]

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.
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