N-Nitroso-N-methylurea

N-Nitroso-N-methylurea

Skeletal formula of N-nitroso-N-methylurea
Ball and stick model of N-nitroso-N-methylurea Spacefill model of N-nitroso-N-methylurea
Names
IUPAC name 1-Methyl-1-nitrosourea
Identifiers
CAS Number	684-93-5 Y
Abbreviations	NMU
Beilstein Reference	1756040
ChEBI	CHEBI:50102 N
ChEMBL	ChEMBL288958 N
ChemSpider	12177 N
EC Number	211-678-4
Jmol 3D model	Interactive image Interactive image
KEGG	C14595 Y
MeSH	Methylnitrosourea
PubChem	12699
InChI InChI=1S/C2H5N3O2/c1-5(4-7)2(3)6/h1H3,(H2,3,6) N Key: ZRKWMRDKSOPRRS-UHFFFAOYSA-N N
SMILES Cn(:n:[o]):c(:[nH2]):[o] CN(N=O)C(N)=O
Properties
Chemical formula	C2H5N3O2
Molar mass	103.08 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 Deuterated DMF
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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, which can lead to AT:GC transition mutations.

NMU is the traditional precursor in the synthesis of diazomethane. However, because it is unstable at temperatures beyond 20 °C and somewhat shock-sensitive, it has become obsolete for this purpose and replaced by other N-nitroso compounds: (N-methyl)nitrosamides and nitrosamines. 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 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, mammary carcinomas, leukemia, 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, fetal growth retardation, and increased fetal resorption. Exposure to NMU during pre-implantation, post-implantation, organogenesis, or by paternal exposure can result in these effects.