N-Nitroso-N-methylurea

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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
Identifiers
Abbreviations NMU[citation needed]
CAS number 684-93-5 YesY
PubChem 12699
ChemSpider 12177 N
EC number 211-678-4
KEGG C14595 YesY
MeSH Methylnitrosourea
ChEBI CHEBI:50102 N
ChEMBL CHEMBL288958 N
Beilstein Reference 1756040
Jmol-3D images Image 1
Image 2
Properties
Molecular 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
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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, 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[edit]

  1. ^ "Methylnitrosourea - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 1 May 2012. 
  2. ^ Hazardous Substance Fact Sheet for NMU New Jersey Department of Health and Senior Services
  3. ^ a b c NMU Substance Profile NTP, Report on Carcinogens, Eleventh Edition
  4. ^ Wada, A., et al. (1994). Induction of Congenital Malformations in Mice by Paternal Methylnitrosourea Treatment. Congenital Anomalies 34:65-70.
  5. ^ Nagao, T., et al. (1991). Induction of Fetal Malformations After Treatment of Mouse Embryos with Methylnitrosourea at the Preimplantation Stages. Teratogenesis, Carcinogenesis, and Mutagenesis 11:1-10.
  6. ^ Faustman, E., et al. (1989). In Vitro Developmental Toxicity of Five Direct-Acting Alkylating Agents in Rodent Embryos: Structure-Activity Patterns. Teratology 40:199-210.