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). verify (what is ?) Infobox references

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

^ ^a ^b Merck Index, 11th Edition, 6017.
^ 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.
^ "Forward and reverse mutagenesis in C. elegans". WormBook. Retrieved 2021-12-01.
^ 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.
^ N-METHYL-N'-NITRO-N-NITROSOGUANIDINE (MNNG), International Agency for Research on Cancer
^ 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.

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

[Lawley_Thatcher_pp._693–707-2] 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.

[WormBook-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

[Hollaender1971-6] 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.

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