Methylnitronitrosoguanidine

Methylnitronitrosoguanidine[1]
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 ;
3D model (JSmol)	Interactive image;
Abbreviations	MNNG
ChemSpider	6025 ;
ECHA InfoCard	100.000.664
KEGG	C14592 ;
PubChem CID	6261;
UNII	12H3O2UGSF [CAS];
CompTox Dashboard (EPA)	DTXSID2020846 ;
	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.

One of the earliest uses of methylnitronitrosoguanidine was in 1985. A group of scientists tested whether or not the chemical composition of methylnitronitrosoguanidine would directly affect the growth of tumors and cancer cells in rats.

In the experiment, the cancer cells from a Japanese cancer patient was injected into 8 rats. The biochemical tool and showed a decline of cancer cells in a few of the rats' bodies.

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

Merck Index, 11th Edition, 6017.
T. Howard Black (1983). "The Preparation and Reactions of Diazomethane" (PDF). Aldrichimica Acta. 16 (1).
N-METHYL-N'-NITRO-N-NITROSOGUANIDINE (MNNG), International Agency for Research on Cancer

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[Merck-1] Merck Index, 11th Edition, 6017.

[2] T. Howard Black (1983). "The Preparation and Reactions of Diazomethane" (PDF). Aldrichimica Acta. 16 (1).

[3] N-METHYL-N'-NITRO-N-NITROSOGUANIDINE (MNNG), International Agency for Research on Cancer