N-Nitroso-N-methylurea

N-Nitroso-N-methylurea
IUPAC name 1-Methyl-1-nitrosourea[1]
Identifiers
Abbreviations	NMU[citation needed]
CAS number	684-93-5 Y
PubChem	12699
ChemSpider	12177 Y
EC number	211-678-4
KEGG	C14595 Y
MeSH	Methylnitrosourea
ChEBI	CHEBI:50102 Y
ChEMBL	CHEMBL288958 Y
Beilstein Reference	1756040
Jmol-3D images	Image 1 Image 2
SMILES Cn(:n:[o]):c(:[nH2]):[o] CN(N=O)C(N)=O
InChI InChI=1S/C2H5N3O2/c1-5(4-7)2(3)6/h1H3,(H2,3,6) Y Key: ZRKWMRDKSOPRRS-UHFFFAOYSA-N Y
Properties
Molecular formula	C2H5N3O2
Molar mass	103.08 g mol−1
Exact mass	103.038176419 g mol−1
log P	−0.302
Acidity (pKa)	12.365
Basicity (pKb)	1.632
Related compounds
Related ureas	ENU
Related compounds	N-Methylformamide Dimethylformamide Biuret
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

N-Nitroso-N-methylurea (NMU) is a highly reliable carcinogen, mutagen, 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. 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.^[2] NMU is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity in experimental animals (IARC 1972, 1978, 1987).^[3] Various cancers induced in animal models include: squamous cell carcinomas of the forestomach, sarcomas and gliomas of the brain, adenocarcinomas of the pancreas, leukemia, and lymphomas.^[3] However, the actual potential for human exposure is quite limited, as the chemical is not produced or used in large quantities ^[3]

NMU is teratogenic and embryotoxic, resulting in craniofacial (cleft palate) and skeletal defects, increased fetal resorption, and fetal growth retardation.^[4][5][6] Exposure to NMU during pre-implantation, post-implantation, organogenesis, or by paternal exposure can result in these effects.

References