N-Nitroso-N-methylurea
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| Names | |||
|---|---|---|---|
| IUPAC name
1-Methyl-1-nitrosourea[1] | |||
| Identifiers | |||
684-93-5  | |||
| 3D model (Jmol) | Interactive image Interactive image | ||
| Abbreviations | NMU | ||
| 1756040 | |||
| ChEBI | CHEBI:50102  | ||
| ChEMBL | ChEMBL288958 | ||
| ChemSpider | 12177 | ||
| ECHA InfoCard | 100.010.618 | ||
| EC Number | 211-678-4 | ||
| KEGG | C14595 | ||
| MeSH | Methylnitrosourea | ||
| PubChem | 12699 | ||
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| Properties | |||
| 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 |
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| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
| verify (what is ?) | |||
| 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.[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, mammary carcinomas, 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, fetal growth retardation, and increased fetal resorption.[4][5][6] Exposure to NMU during pre-implantation, post-implantation, organogenesis, or by paternal exposure can result in these effects.
References
- ↑ "Methylnitrosourea - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 1 May 2012.
- ↑ Hazardous Substance Fact Sheet for NMU New Jersey Department of Health and Senior Services
- 1 2 3 NMU Substance Profile NTP, Report on Carcinogens, Eleventh Edition
- ↑ Wada, A., et al. (1994). Induction of Congenital Malformations in Mice by Paternal Methylnitrosourea Treatment. Congenital Anomalies 34:65-70.
- ↑ 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.
- ↑ 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.