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

carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subs ...

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 DNA mismatch repair (MMR) is a system for recognizing and repairing erroneous insertion, deletion, and mis-incorporation of bases that can arise during DNA replication and recombination, as well as repairing some forms of DNA damage. Mismatch ...

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 Diazomethane is the chemical compound CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost ...

when reacted with aqueous

potassium hydroxide Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which exp ...

. MNNG is a probable human carcinogen listed as an IARC Group 2A carcinogen.N-METHYL-N'-NITRO-N-NITROSOGUANIDINE (MNNG)

International Agency for Research on Cancer The International Agency for Research on Cancer (IARC; french: Centre International de Recherche sur le Cancer, CIRC) is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and ...

Stability

MNNG produces

(known DNA methylating agent) in basic aqueous solutions, and

nitrous acid Nitrous acid (molecular formula ) is a weak and monoprotic acid known only in solution, in the gas phase and in the form of nitrite () salts. Nitrous acid is used to make diazonium salts from amines. The resulting diazonium salts are reagent ...

(also mutagenic) in acidic solutions.

References

{{reflist IARC Group 2A carcinogens Mutagens Nitroguanidines Nitrosoguanidines