N-Nitroso-N-methylurea
Encyclopedia
N-Nitroso-N-methylurea (NMU) is a highly reliable carcinogen
Carcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...

, mutagen
Mutagen
In genetics, a mutagen is a physical or chemical agent that changes the genetic material, usually DNA, of an organism and thus increases the frequency of mutations above the natural background level. As many mutations cause cancer, mutagens are therefore also likely to be carcinogens...

, and teratogen. NMU is an alkylating agent, and exhibits its toxicity by transferring its methyl group to nucleobases in nucleic acids.

NMU is the traditional precursor in the synthesis of diazomethane
Diazomethane
Diazomethane is the chemical compound CH2N2. It is the simplest of diazo compounds. In the pure form at room temperature, it is a extremely sensitive explosive yellow gas, thus it is almost universally used as a solution in diethyl ether...

. However, since it is unstable at temperatures beyond 20 °C and shock-sensitive to a degree, for this purpose it has become obsolete and replaced by other (N-methyl)nitrosamides. Most chemical supply houses have stopped carrying it.

Acute exposure to NMU in humans can result in skin and eye irritation, headache, nausea, and vomiting. NMU is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity in experimental animals (IARC
International Agency for Research on Cancer
The International Agency for Research on Cancer is an intergovernmental agency forming part of the World Health Organisation of the United Nations....

 1972, 1978, 1987). Various cancers induced in animal models include: squamous cell carcinomas of the forestomach, sarcomas and gliomas of the brain, adenocarcinomas of the pancreas, leukemia
Leukemia
Leukemia or leukaemia is a type of cancer of the blood or bone marrow characterized by an abnormal increase of immature white blood cells called "blasts". Leukemia is a broad term covering a spectrum of diseases...

, and lymphomas. However, the actual potential for human exposure is quite limited, as the chemical is not produced or used in large quantities

NMU is teratogenic and embryotoxic, resulting in craniofacial (cleft palate) and skeletal defects, increased fetal resorption, and fetal growth retardation. Exposure to NMU during pre-implantation, post-implantation, organogenesis, or by paternal exposure can result in these effects.
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