メチルニトロソウレア
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/07/25 16:36:16」(JST)
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N-Nitroso-N-methylurea
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| Names |
Preferred IUPAC name
N-Methyl-N-nitrosourea[1]
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| Other names
1-Methyl-1-nitrosourea
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| Identifiers |
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CAS Number
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3D model (JSmol)
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- Interactive image
- Interactive image
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| Abbreviations |
NMU[citation needed] |
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Beilstein Reference
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1756040 |
| ChEBI |
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| ChemSpider |
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| ECHA InfoCard |
100.010.618 |
| EC Number |
211-678-4 |
| KEGG |
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| MeSH |
Methylnitrosourea |
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InChI
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InChI=1S/C2H5N3O2/c1-5(4-7)2(3)6/h1H3,(H2,3,6) N
Key: ZRKWMRDKSOPRRS-UHFFFAOYSA-N N
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SMILES
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Cn(:n:[o]):c(:[nH2]):[o]
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CN(N=O)C(N)=O
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| Properties |
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Chemical formula
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C2H5N3O2 |
| Molar mass |
103.08 g·mol−1 |
| log P |
−0.302 |
| Acidity (pKa) |
12.365 |
| Basicity (pKb) |
1.632 |
| Related compounds |
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Related ureas
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ENU |
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Related compounds
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- N-Methylformamide
- Dimethylformamide
- Deuterated DMF
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) |
| Infobox references |
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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
- ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 663. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001.
- ^ Hazardous Substance Fact Sheet for NMU New Jersey Department of Health and Senior Services
- ^ a b c 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.
English Journal
- N-methylnitrosourea aggravates gastrointestinal polyposis in Lkb1+/- mice.
- Udd L, Gao Y, Ristimäki AP, Mäkelä TP.SourceInstitute of Biotechnology, University of Helsinki, Helsinki 00014, Finland and.
- Carcinogenesis.Carcinogenesis.2013 Jul 2. [Epub ahead of print]
- Peutz-Jeghers patients develop hamartomatous polyps and carcinomas of the gastrointestinal tract. Cyclooxygenase-2 accelerates polyp growth in Lkb1 +/- mice modelling Peutz-Jeghers polyposis. In this study, we aimed to evaluate the effect of the mutagenic carcinogen N-methylnitrosourea (MNU) on gast
- PMID 23722652
- Iodine and doxorubicin, a good combination for mammary cancer treatment: antineoplastic adjuvancy, chemoresistance inhibition, and cardioprotection.
- Alfaro Y, Delgado G, Cárabez A, Anguiano B, Aceves C.SourceInstituto de Neurobiología, Universidad Nacional Autónoma de México, Campus-Juriquilla, Querétaro 76230, México. caracev@unam.mx.
- Molecular cancer.Mol Cancer.2013 May 24;12:45. doi: 10.1186/1476-4598-12-45.
- BACKGROUND: Although mammary cancer (MC) is the most common malignant neoplasia in women, the mortality for this cancer has decreased principally because of early detection and the use of neoadjuvant chemotherapy. Of several preparations that cause MC regression, doxorubicin (DOX) is the most active
- PMID 23705792
- Diffusion Weighted Imaging Evaluated the Early Therapy Effect of Tamoxifen in an MNU-Induced Mammary Cancer Rat Model.
- Zhai G, Grubbs CJ, Stockard CR, Umphrey HR, Beasley TM, Kim H.SourceThe Department of Radiology, The University of Alabama at Birmingham, Birmingham, Alabama, United States of America.
- PloS one.PLoS One.2013 May 21;8(5):e64445. doi: 10.1371/journal.pone.0064445. Print 2013.
- PURPOSE: To assess the optimal time point of diffusion-weighted imaging (DWI) for early prognosis of breast cancer following tamoxifen therapy using a methylnitrosourea (MNU)-induced ER-positive breast-cancer model.METHODS: Two groups of Sprague-Dawley rats (n = 15 for group 1; n = 10 for gr
- PMID 23700476
Japanese Journal
- メチルニトロソ尿素 (MNU)の発達期暴露によるマウス海馬歯状回におけるニューロン新生への影響
- ラット海馬歯状回でのニューロン新生開始時期である胎齢後期でのメチルニトロソ尿素（MNU）の短期間投与による離乳時ニューロン新生への影響
- 母動物へのmethylnitrosourea単回腹腔内投与によるマウス児動物海馬歯状回のニューロン新生に対する影響
Related Links
- Induction of Congenital Malformations in Mice by Paternal Methylnitrosourea Treatment. Congenital ... Induction of Fetal Malformations After Treatment of Mouse Embryos with Methylnitrosourea at the Preimplantation Stages. Teratogenesis ...