Methylnitronitrosoguanidine

Methylnitronitrosoguanidine[1]
Structural formula of methylnitronitrosoguanidine
Space-filling model of the methylnitronitrosoguanidine molecule
Names
Preferred IUPAC name
N-Methyl-N′-nitro-N-nitrosoguanidine
Other names
1-Methyl-3-nitro-1-nitrosoguanidine
N-Methyl-N-nitroso-N′-nitroguanidine
Identifiers
3D model (JSmol)
Abbreviations MNNG
ChemSpider
ECHA InfoCard 100.000.664 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C2H5N5O3/c1-6(5-8)2(3)4-7(9)10/h1H3,(H2,3,4) ☒N
    Key: VZUNGTLZRAYYDE-UHFFFAOYSA-N ☒N
  • InChI=1/C2H5N5O3/c1-6(5-8)2(3)4-7(9)10/h1H3,(H2,3,4)
    Key: VZUNGTLZRAYYDE-UHFFFAOYAT
  • CN(C(=N[N+](=O)[O-])N)N=O
Properties
C2H5N5O3
Molar mass 147.09 g/mol
Appearance Yellow crystals
Melting point 118 °C (244 °F; 391 K) (decomposes)
reacts violently, slowly hydrolysed
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methylnitronitrosoguanidine (MNNG[2] or MNG, NTG when referred to colloquially as nitrosoguanidine[3]) is a biochemical tool used experimentally as a carcinogen and mutagen.[1] It acts by adding alkyl groups to the O6 of guanine and O4 of thymine, which can lead to transition mutations between GC and AT. These changes do not cause a heavy distortion in the double helix of DNA and thus are hard to detect by the DNA mismatch repair system.

In organic chemistry, MNNG is used as a source of diazomethane when reacted with aqueous potassium hydroxide.[4]

MNNG is a probable human carcinogen listed as an IARC Group 2A carcinogen.[5]

Stability

MNNG produces diazomethane, a known methylating agent of DNA and other substrates, in basic aqueous solutions, and nitrous acid, a mutagen, in acidic solutions.[6]

References

  1. ^ a b Merck Index, 11th Edition, 6017.
  2. ^ Lawley, P. D.; Thatcher, Carolyn J. (1970-02-01). "Methylation of deoxyribonucleic acid in cultured mammalian cells by N-methyl-N′-nitro-N-nitrosoguanidine. The influence of cellular thiol concentrations on the extent of methylation and the 6-oxygen atom of guanine as a site of methylation". Biochemical Journal. 116 (4). Portland Press Ltd.: 693–707. doi:10.1042/bj1160693. ISSN 0306-3283. PMC 1185415. PMID 5435496.
  3. ^ "Forward and reverse mutagenesis in C. elegans". WormBook. Retrieved 2021-12-01.
  4. ^ T. Howard Black (1983). "The Preparation and Reactions of Diazomethane" (PDF). Aldrichimica Acta. 16 (1): 3–10. Archived from the original (PDF) on 2019-02-03. Retrieved 2024-10-13.
  5. ^ N-METHYL-N'-NITRO-N-NITROSOGUANIDINE (MNNG), International Agency for Research on Cancer
  6. ^ Hollaender, Alexander (1971). Chemical Mutagens: Principles and Methods for Their Detection. Vol. 1. Springer Publishing. p. 188. ISBN 978-1-4615-8966-2. OCLC 851813793.