Methylnitronitrosoguanidine

Methylnitronitrosoguanidine

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
CAS Number	70-25-7 checkY
3D model (JSmol)	Interactive image
Abbreviations	MNNG
ChemSpider	6025 ☒N
ECHA InfoCard
E number
KEGG	C14592 checkY
PubChem CID	6261
UNII	12H3O2UGSF checkY[CAS]
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI 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
SMILES CN(C(=N[N+](=O)[O-])N)N=O
Properties
Chemical formula	C2H5N5O3
Molar mass	147.09 g/mol
Appearance	Yellow crystals
Melting point	118 °C (244 °F; 391 K) (decomposes)
Solubility in water	reacts violently, slowly hydrolysed
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

Methylnitronitrosoguanidine (MNNG or MNG, NTG when referred to colloquially as nitrosoguanidine) is a biochemical tool used experimentally as a carcinogen and mutagen. 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.

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

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.