N-亚硝基甲乙胺 | 10595-95-6

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-亚硝基甲乙胺
• 中文别名: N-亚硝基甲基乙基胺；甲基乙基亚硝胺；N-亚硝基-N-甲基乙胺；N-亚硝基甲乙胺N-Nitroso-methylethylamine
• 英文名称: N-nitrosomethylethylamine
• 英文别名: N-nitroso-N-methylethylamine；N-methyl-N-ethylnitrosamine；N-nitrosoethylmethylamine；ethyl-methyl-nitroso-amine；Aethyl-methyl-nitroso-amin；N-ethyl-N-methylnitrous amide
• CAS: 10595-95-6
• 化学式: C₃H₈N₂O
• mdl: MFCD00015802
• 分子量: 88.1093
• InChiKey: RTDCJKARQCRONF-UHFFFAOYSA-N

物化性质

• 沸点：
  170℃
• 密度：
  0.9448 g/cm3 (18 ºC)
• 闪点：
  76 °C
• 溶解度：
  氯仿：微溶；乙酸乙酯：微溶；甲醇：微溶
• 物理描述：
  Pale yellow oil.
• 颜色/状态：
  Yellow liquid
• 蒸汽密度：
  0.945
• 蒸汽压力：
  1.1 mm Hg at 20 °C (est)
• 稳定性/保质期：
  1. 存在于烟气中。
  2. 有致癌的可能性。
• 分解：
  When heated to decomposition it emits toxic fumes of /oxides of nitrogen/.
• 保留指数：
  802

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

代谢

成年雄性Fischer 344大鼠单次腹腔注射或口服给予N-亚硝基甲基乙基胺（4.4 mg/kg，0.05 mmol/kg），其甲基或乙基团上标记有（14C），存活时间为4小时。DNA在0.1 M HCl中酸水解后，通过Sephasorb-HP色谱进行分析。肝脏DNA中7-甲基鸟嘌呤的浓度比7-乙基鸟嘌呤高170-200倍。这大约是当DNA与等摩尔量的直接烷化剂N-亚硝基甲基脲和N-亚硝基乙基脲反应时观察到的7-甲基鸟嘌呤：7-乙基鸟嘌呤比率68的2.6倍，表明N-亚硝基甲基乙基胺的乙基基团α位的羟基化速率大约是甲基基团的2.6倍。肝脏中7-甲基鸟嘌呤的浓度大约是肾脏的15倍，食道的100倍，肺的200倍。在饮用水中添加乙醇（5%）会导致代谢在器官间轻微转移，肝脏与食道的7-甲基鸟嘌呤比率降低50%，肝脏与肾脏的7-甲基鸟嘌呤比率增加40%。

... Adult male Fischer 344 rats received a single i.p. or p.o. dose (4.4 mg/kg, 0.05 mmol/kg) of N-nitrosomethylethylamine, (14C)-labeled in either the methyl or ethyl group (survival time, 4 hr). DNA was analyzed by Sephasorb-HP chromatography following acid hydrolysis in 0.1 M HCl. Concentrations of 7-methylguanine in hepatic DNA were 170-200 times higher than those of 7-ethylguanine. This is approximately 2.6 times the 7-methylguanine: 7-ethylguanine ratio of 68, observed when DNA is reacted in vitro with equimolar amounts of the direct alkylating agents N-nitrosomethylurea and N-nitrosoethylurea, suggesting that hydroxylation at the alpha-position of the ethyl group of N-nitrosomethylethylamine proceeds at about 2.6 times the rate as at the methyl group. Concentrations of 7-methylguanine in liver were approximately 15 times higher than in kidney, 100 times higher than in esophagus, and 200 times higher than in lung. Addition of ethanol to the drinking water (5%) caused a slight interorgan shift in metabolism with a decrease in the 7-methylguanine ratio for liver: esophagus by 50% and an increase in the 7-methylguanine ratio for liver: kidney by 40%.

来源:Hazardous Substances Data Bank (HSDB)

代谢

Sprague-Dawley 大鼠肝微粒体对 N-甲基乙基亚硝胺 (MEN) 的氧化脱烷基化反应通过一种用于同时分析甲醛和乙醛的分光光度法进行了研究。在每种情况下，脱烷基化都遵循米氏-门登动力学。 ... MEN 的去甲基化和去乙基化的米氏常数 (Km) 值介于 N-二甲基亚硝胺和 N-二乙基亚硝胺之间。 ...

OThe oxidative dealkylation of ... methylethylnitrosamine (MEN) by Sprague-Dawley rat liver microsomes was studied by a colorimetric assay for the simultaneous analysis of formaldehyde and acetaldehyde. Dealkylation in each instance followed Michaelis-Menten kinetics. ... Km values for demethylation and deethylation of MEN were intermediate between those for dimethylnitrosamine and diethylnitrosamine. ...

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠小肠中，研究了亚硝胺的结构与代谢之间可能存在的关系。从肠腔侧对空肠和回肠的孤立段进行了2小时的灌注，使用的是含有四种对称二烷基亚硝胺之一的Tyrode溶液，每个侧链有2-5个碳原子，均在α位置标记有(14)C，或者含有两种不对称亚硝胺之一，即N-亚硝基叔丁基甲胺和N-亚硝基甲基苄胺，在甲基组中标记有(14)C。除了测量(14)C到肠组织外，还分析了吸收的液体（吸收液）以及灌注介质和组织匀浆中极性代谢物的存在，以评估亚硝胺的肠内代谢。N-亚硝基二乙胺和两种不对称亚硝胺均未显著代谢。

Possible relationships between structure and metabolism of nitrosamines have been investigated in the rat small intestine. Isolated segments of jejunum and ileum were perfused from the luminal side for 2 hr with a Tyrode solution containing one of four symmetrical dialkylnitrosamines with 2-5 carbon atoms per side chain, all (14)C-labeled at the alpha position, or one of two unsymmetrical nitrosamines, N-nitroso-tert-butylmethylamine and N-nitrosomethylbenzylamine, (14)C-labeled in the methyl group. Besides measurement of (14)C to intestinal tissue, the absorbed fluid (absorbate) as well as the perfusion medium and tissue homogenates were analysed by for the presence of polar metabolites to assess the intestinal metabolism of nitrosamines. Neither N-nitrosodiethylamine nor the two unsymmetrical nitrosamines were metabolized to any significant extent.

来源:Hazardous Substances Data Bank (HSDB)

代谢

乙基甲基亚硝胺已知的人类代谢物包括N-亚硝基乙胺和N-亚硝基甲胺。

Ethylmethylnitrosamine has known human metabolites that include N-Nitrosoethanamine and N-Nitrosomethylamine.

来源:NORMAN Suspect List Exchange

毒理性

• 致癌性证据

没有关于人类的数据。动物中有充分的致癌性证据。总体评估：2B组：该物质可能对人类有致癌性。

No data are available in humans. Sufficient evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 2B: The agent is possibly carcinogenic to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

分类：B2；可能的人类致癌物。分类依据：在大鼠的两个品系中，肝脏和其他部位肿瘤发生率增加。人类致癌性数据：不足。动物致癌性数据：充分。

CLASSIFICATION: B2; probable human carcinogen. BASIS FOR CLASSIFICATION: Increased incidences of tumors of the liver and other sites in two rat strains. HUMAN CARCINOGENICITY DATA: Inadequate. ANIMAL CARCINOGENICITY DATA: Sufficient.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：N-亚硝基甲基乙基胺

IARC Carcinogenic Agent:N-Nitrosomethylethylamine

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：2B组：可能对人类致癌

IARC Carcinogenic Classes:Group 2B: Possibly carcinogenic to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第17卷：（1978年）一些N-亚硝基化合物

IARC Monographs:Volume 17: (1978) Some N-Nitroso Compounds

来源:International Agency for Research on Cancer (IARC)

安全信息

• 危险等级：
  6.1(b)
• 海关编码：
  2928000090
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 危险品运输编号：
  UN 2810
• 储存条件：
  室温

制备方法与用途

用途：用于生化研究。

反应信息

• 作为反应物：
  描述：

  N-亚硝基甲乙胺 在 盐酸 作用下， 生成 N-乙基甲基胺
  参考文献：
  名称：

  245.环状亚甲基胺。季化合物的水解。脂肪族仲胺的制备。第一部分

  摘要：

  DOI：

  10.1039/jr9380001311
• 作为产物：
  描述：

  N-Nitrosomethyl-N-1-methyl-2-oxopropylamine 在 sodium hydroxide 作用下， 以95%的产率得到N-亚硝基甲乙胺
  参考文献：
  名称：

  Saavedra, Joseph E.; Farnsworth, David W.; Farrelly, James G., Synthetic Communications, 1989, vol. 19, # 7,8, p. 1147 - 1156

  摘要：

  DOI：

文献信息

• Synthesis and properties of 2-hydroxyethyl derivatives of methylene-bis(1-oxy-3, 3-dialkyl-1-triazene 2-oxides)
  作者：G. A. Smirnov、S. V. Nikitin、P. B. Gordeev、G. V. Pokhvisneva、T. V. Ternikova、O. A. Luk’yanov

  DOI：10.1007/s11172-015-1211-0

  日期：2015.11

  Synthetic approach to 2-hydroxyethyl derivatives of methylene-bis(1-oxy-3, 3-dialkyl-1triazene 2-oxides), promising NO donors, which can release NO in living organisms was developed. Some transformations of the hydroxyethyl moiety of the synthesized compounds were studied.

  开发了亚甲基-双（1-氧基-3，3-二烷基-1三氮烯 2-氧化物）的 2-羟乙基衍生物的合成方法，有前途的 NO 供体，可以在活生物体中释放 NO。研究了合成化合物的羟乙基部分的一些转化。
• Peroxytrifluoroacetic Acid. II. The Oxidation of Anilines to Nitrobenzenes¹
  作者：William D. Emmons

  DOI：10.1021/ja01642a030

  日期：1954.7
• Jensen,K.A. et al., Acta Chemica Scandinavica (1947), 1961, vol. 15, p. 1109 - 1123
  作者：Jensen,K.A. et al.

  DOI：——

  日期：——
• Seebach,D.; Enders,D., Chemische Berichte, 1975, vol. 108, p. 1293 - 1320
  作者：Seebach,D.、Enders,D.

  DOI：——

  日期：——
• Piotrowska,K., Synthetic Communications, 1979, vol. 9, p. 765 - 770
  作者：Piotrowska,K.

  DOI：——

  日期：——

表征谱图