Methylnitronitrosoguanidine

Methylnitronitrosoguanidine^[1]

Names
IUPAC name 1-methyl-3-nitro-1-nitrosoguanidine
Other names N-Methyl-N-nitroso-N′-nitroguanidine; N-Methyl-N′-nitro-N-nitrosoguanidine
Identifiers
CAS Number	70-25-7
3D model (Jmol)	Interactive image
Abbreviations	MNNG
ChemSpider	6025
ECHA InfoCard	100.000.664
KEGG	C14592
PubChem	6261
InChI InChI=1S/C2H5N5O3/c1-6(5-8)2(3)4-7(9)10/h1H3,(H2,3,4) Key: VZUNGTLZRAYYDE-UHFFFAOYSA-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).
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Infobox references

Methylnitronitrosoguanidine (MNNG or MNG) 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.^[2]

MNNG is a probable human carcinogen listed as an IARC Group 2A carcinogen.^[3]

References

1. Merck Index, 11th Edition, 6017.
2. Aldrichimica Acta. 16 (3). 1983. Missing or empty |title= (help)
3. N-METHYL-N'-NITRO-N-NITROSOGUANIDINE (MNNG), International Agency for Research on Cancer