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{{DISPLAYTITLE:''N''-Nitroso-''N''-methylurea}} |
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{{DISPLAYTITLE:''N''-Nitroso-''N''-methylurea}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Name=''N''-Nitroso-''N''-methylurea |
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| verifiedrevid = 396604052 |
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|ImageFileL1=N-nitroso-N-methylurea-2D.png |
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| Name = ''N''-Nitroso-''N''-methylurea |
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| verifiedrevid = 433348593 |
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|ImageSizeL1=100px |
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|ImageNameL1=] of ''N''-nitroso-''N''-methylurea |
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| ImageFile = N-Nitroso-N-methylurea.svg |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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|ImageFileR1=N-nitroso-N-methylurea-from-xtal-3D-balls.png |
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| ImageSize = 100 |
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|ImageSizeR1=120px |
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| ImageName = Skeletal formula of N-nitroso-N-methylurea |
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|IUPACName=1-Methyl-1-nitrosourea |
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| ImageFileL1 = N-nitroso-N-methylurea-from-xtal-3D-balls.png |
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|OtherNames= |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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|Section1={{Chembox Identifiers |
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| ImageNameL1 = Ball and stick model of N-nitroso-N-methylurea |
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| Abbreviations=NMU |
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| ImageFileR1 = N-nitroso-N-methylurea-from-xtal-3D-vdW.png |
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| CASNo_Ref = {{cascite}} |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| CASNo=684-93-5 |
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| ImageNameR1 = Spacefill model of N-nitroso-N-methylurea |
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| PubChem=12699 |
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| PIN = ''N''-Methyl-''N''-nitrosourea<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 663 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| OtherNames = 1-Methyl-1-nitrosourea |
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| Section1 = {{Chembox Identifiers |
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| Abbreviations = NMU{{citation needed|date=May 2012}} |
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| CASNo = 684-93-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = W8KW4E3XSU |
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| PubChem = 12699 |
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| ChemSpiderID = 12177 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| EINECS = 211-678-4 |
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| KEGG = C14595 |
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| KEGG = C14595 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| SMILES=CN(C(=O)N)N=O |
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| MeSHName = Methylnitrosourea |
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| ChEBI = 50102 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 288958 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| Beilstein = 1756040 |
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| SMILES = CN(N=O)C(N)=O |
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| StdInChI = 1S/C2H5N3O2/c1-5(4-7)2(3)6/h1H3,(H2,3,6) |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = ZRKWMRDKSOPRRS-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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|Section2={{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula=C<sub>2</sub>H<sub>5</sub>N<sub>3</sub>O<sub>2</sub> |
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| C=2 | H=5 | N=3 | O=2 |
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| MolarMass=103.08 g/mol |
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| LogP = −0.302 |
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| Appearance= |
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| pKa = 12.365 |
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| Density= |
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| pKb = 1.632 |
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|Section3={{Chembox Hazards |
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| Section3 = {{Chembox Related |
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| MainHazards= |
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| OtherFunction_label = ureas |
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| FlashPt= |
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| OtherFunction = ] |
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| Autoignition= |
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| OtherCompounds = {{Unbulleted list|]|]|]}} |
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'''''N''-Nitroso-''N''-methylurea''' (NMU) is a highly reliable ], ], and ]. NMU is an alkylating agent, and exhibits its toxicity by transferring its ] group to ] in ]. |
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'''''N''-Nitroso-''N''-methylurea''' ('''NMU''') is a highly reliable ], ], and ]. NMU is an ], and exhibits its toxicity by transferring its ] group to ] in ], which can lead to AT:GC ] mutations. |
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NMU is the traditional precursor in the synthesis of ]. 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. |
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NMU is the traditional precursor in the synthesis of ].<ref>{{cite journal |title=NITROSOMETHYLUREA |journal=Organic Syntheses |date=1935 |volume=15 |pages=48 |doi=10.15227/orgsyn.015.0048}}</ref><ref>{{cite journal |title=DIAZOMETHANE |journal=Organic Syntheses |date=1935 |volume=15 |pages=3 |doi=10.15227/orgsyn.015.0003}}</ref> It has the potentially advantageous property that the stoichiometric byproducts formed are water, carbon dioxide, and ammonia, which are innocuous or easily removed. 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 ]s. Most chemical supply houses have stopped carrying it. |
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Acute exposure to NMU in humans can result in skin and eye irritation, headache, nausea, and vomiting.<ref name="NJ1"> New Jersey Department of Health and Senior Services</ref> NMU is ''reasonably anticipated to be a human carcinogen'' based on sufficient evidence of carcinogenicity in experimental animals (] 1972, 1978, 1987).<ref name="NTP1"> NTP, Report on Carcinogens, Eleventh Edition</ref> Various cancers induced in animal models include: squamous cell ] of the forestomach, ] and ] of the brain, ] of the pancreas, ], and ].<ref name="NTP1"/> However, the actual potential for human exposure is quite limited, as the chemical is not produced or used in large quantities <ref name="NTP1"/> |
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Acute exposure to NMU in humans can result in skin and eye irritation, headache, nausea, and vomiting.<ref name="NJ1"> New Jersey Department of Health and Senior Services</ref> NMU is ''reasonably anticipated to be a human carcinogen'' based on sufficient evidence of carcinogenicity in experimental animals (] 1972, 1978, 1987).<ref name="NTP1"> NTP, Report on Carcinogens, Eleventh Edition</ref> Various cancers induced in animal models include: squamous cell ]s of the forestomach, ]s and ]s of the brain, ]s of the pancreas, mammary carcinomas, ], and ]s.<ref name="NTP1"/> However, the actual potential for human exposure is quite limited, as the chemical is not produced or used in large quantities <ref name="NTP1"/> |
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NMU is teratogenic and embryotoxic, resulting in craniofacial (]) and skeletal defects, increased fetal resorption, and fetal growth retardation.<ref name="wada">Wada, A., et al. (1994). Induction of Congenital Malformations in Mice by Paternal Methylnitrosourea Treatment. Congenital Anomalies '''34''':65-70.</ref><ref name="Nagao">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.</ref><ref name="Faustman">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.</ref> Exposure to NMU during pre-implantation, post-implantation, organogenesis, or by paternal exposure can result in these effects. |
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NMU is teratogenic and embryotoxic, resulting in craniofacial (]) and skeletal defects, fetal growth retardation, and increased ].<ref name="wada">Wada, A., et al. (1994). Induction of Congenital Malformations in Mice by Paternal Methylnitrosourea Treatment. Congenital Anomalies '''34''':65-70.</ref><ref name="Nagao">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.</ref><ref name="Faustman">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.</ref> Exposure to NMU during pre-implantation, post-implantation, organogenesis, or by paternal exposure can result in these effects. |
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==References== |
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==References== |
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{{Reflist}} |
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<references/> |
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==External links== |
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*{{Commonscatinline}} |
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{{DEFAULTSORT:Nitroso-N-methylurea, N-}} |
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{{DEFAULTSORT:Nitroso-N-methylurea, N-}} |
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