N-Nitroso-N-methylurea

N-Nitroso-N-methylurea
	Skeletal formula of N-nitroso-N-methylurea
	Template:Chembox image sbs cell
Names
	IUPAC name 1-Methyl-1-nitrosourea
Identifiers
CAS Number	684-93-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:50102 ;
ChEMBL	ChEMBL288958 ;
ChemSpider	12177 ;
ECHA InfoCard	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
KEGG	C14595 ;
MeSH	Methylnitrosourea
PubChem CID	12699;
	InChI InChI=1S/C2H5N3O2/c1-5(4-7)2(3)6/h1H3,(H2,3,6) Key: ZRKWMRDKSOPRRS-UHFFFAOYSA-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
Related compounds
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).
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	Infobox references

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Template:Chembox Abbreviations Template:Chembox Beilstein Template:Chembox ECNumber Template:Chembox E number Template:Chembox LogP Template:Chembox pKa Template:Chembox pKb Template:Chembox OtherFunctn

Overview

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

↑ "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
↑ ^3.0 ^3.1 ^3.2 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.

[1] "Methylnitrosourea - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 1 May 2012.

[NJ1-2] Hazardous Substance Fact Sheet for NMU New Jersey Department of Health and Senior Services

[NTP1-3] 3.0 ^3.1 ^3.2 NMU Substance Profile NTP, Report on Carcinogens, Eleventh Edition

[wada-4] Wada, A., et al. (1994). Induction of Congenital Malformations in Mice by Paternal Methylnitrosourea Treatment. Congenital Anomalies 34:65-70.

[Nagao-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.

[Faustman-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.

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Names
Skeletal formula of N-nitroso-N-methylurea
Template:Chembox image sbs cell
IUPAC name 1-Methyl-1-nitrosourea^[1]
Identifiers
CAS Number	684-93-5^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:50102^N
ChEMBL	ChEMBL288958^N
ChemSpider	12177^N
ECHA InfoCard	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
KEGG	C14595^Y
MeSH	Methylnitrosourea
PubChem CID	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
Related compounds
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

Overview

References

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