1-Cyanomethyl-2-nitromethylenepyrrolidine | 91417-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-Cyanomethyl-2-nitromethylenepyrrolidine
• 英文别名: [(2Z)-2-(nitromethylidene)pyrrolidin-1-yl]acetonitrile；2-[(2Z)-2-(nitromethylidene)pyrrolidin-1-yl]acetonitrile
• CAS: 91417-82-2
• 化学式: C₇H₉N₃O₂
• 分子量: 167.167
• InChiKey: UUBCVVUIZRGQQU-SREVYHEPSA-N

物化性质

• 沸点：
  327.5±42.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.8
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

有机腈通过肝脏中的细胞色素P450酶的作用转化为氰化物离子。氰化物迅速被吸收并在全身分布。氰化物主要通过罗丹酶或3-巯基丙酸硫转移酶代谢为硫氰酸盐。氰化物代谢物通过尿液排出。

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

作为神经递质模拟剂，具有兴奋和抑制效果，最终阻断突触后尼古丁受体。（T10）有机腈在体内和体外均分解成氰化物离子。因此，有机腈的主要毒性机制是它们产生有毒的氰化物离子或氢氰酸。氰化物是电子传递链第四复合体（存在于真核细胞线粒体膜中）中的细胞色素c氧化酶的抑制剂。它与这种酶中的三价铁原子形成复合物。氰化物与这种细胞色素的结合阻止了电子从细胞色素c氧化酶传递到氧气。结果，电子传递链被破坏，细胞无法再通过有氧呼吸产生ATP能量。主要依赖有氧呼吸的组织，如中枢神经系统和心脏，受到特别影响。氰化物也通过结合过氧化氢酶、谷胱甘肽过氧化物酶、变性血红蛋白、羟钴胺素、磷酸酶、酪氨酸酶、抗坏血酸氧化酶、黄嘌呤氧化酶、琥珀酸脱氢酶和Cu/Zn超氧化物歧化酶产生一些毒性效应。氰化物与变性血红蛋白中的三价铁离子结合形成无活性的氰变性血红蛋白。（L97）

Acts as a neurotransmitter mimic , having both excitatory and depressant effects, eventually blocking postsynaptic nicotinic receptors. (T10) Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

亚甲基有神经毒性。(T10)

Nitromethylenes are neurotoxic. (T10)

来源:Toxin and Toxin Target Database (T3DB)

反应信息

• 作为产物：
  描述：

  吡拉西坦 在 吡啶 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 8.83h， 生成 1-Cyanomethyl-2-nitromethylenepyrrolidine
  参考文献：
  名称：

  Synthesis and biological study of pyracetam derivatives and related compounds

  摘要：

  DOI：

  10.1007/bf00758995

文献信息

• Synthesis and biological study of pyracetam derivatives and related compounds
  作者：T. V. Stezhko、V. G. Granik、R. G. Glushkov、L. F. Roshchina、A. I. Polezhaeva、M. D. Mashkovskii

  DOI：10.1007/bf00758995

  日期：1984.3