二苯基胂甲腈 | 23525-22-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 二苯基胂甲腈
• 中文别名: 1H-吲哚-1-羧酸,2-甲基-,甲基酯
• 英文名称: Clark 2
• 英文别名: diphenylcyanoarsine；Diphenyl-cyan-arsin；diphenyl-arsinecarbonitrile；Diphenyl-arsincarbonitril；Diphenylarsencyanid；diphenylarsanylformonitrile
• CAS: 23525-22-6
• 化学式: C₁₃H₁₀AsN
• 分子量: 255.151
• InChiKey: BDHNJKLLVSRGDK-UHFFFAOYSA-N

物化性质

• 物理描述：
  Diphenylcyanoarsine is a colorless liquid, odorless to fruity.

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

砒霜主要通过吸入或摄入被吸收，较少程度上通过皮肤接触。然后它被分布到全身，如果需要，它会被还原成亚砷酸盐，然后通过砷酸盐甲基转移酶甲基化成单甲基砷（MMA）和二甲砷酸（DMA）。砒霜及其代谢物主要通过尿液排出。已知砒霜可以诱导金属结合蛋白金属硫蛋白，通过绑定砒霜和其他金属并使它们生物学上不活跃，以及充当抗氧化剂，从而减少砒霜和其他金属的有毒效果。（L20）有机腈通过肝脏细胞色素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成硫氰酸盐。氰化物代谢物通过尿液排出。（L96）

Arsenic is absorbed mainly by inhalation or ingestion, as to a lesser extent, dermal exposure. It is then distributed throughout the body, where it is reduced into arsenite if necessary, then methylated into monomethylarsenic (MMA) and dimethylarsenic acid (DMA) by arsenite methyltransferase. Arsenic and its metabolites are primarily excreted in the urine. Arsenic is known to induce the metal-binding protein metallothionein, which decreases the toxic effects of arsenic and other metals by binding them and making them biologically inactive, as well as acting as an antioxidant. (L20) 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

砷及其代谢物通过多种机制干扰ATP的产生。在柠檬酸循环层面，砷抑制了丙酮酸脱氢酶，并通过与磷酸竞争，解偶联氧化磷酸化，从而抑制了与能量相关的NAD+的还原、线粒体呼吸和ATP的合成。过氧化氢的产生也增加了，这可能会形成活性氧物种和氧化应激。砷的致癌性受到砷与微管蛋白结合的影响，这会导致非整倍体、多倍体和有丝分裂的停滞。其他砷蛋白靶点的结合也可能导致DNA修复酶活性的改变、DNA甲基化模式的改变和细胞增殖。有机腈在体内和体外都会分解成氰化物离子。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个复合体（存在于真核细胞线粒体膜中）的细胞色素c氧化酶的抑制剂。它与这种酶中的铁原子形成复合物。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方式产生ATP作为能量。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。氰化物还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铁离子结合形成不活性的氰化变性血红蛋白。

Arsenic and its metabolites disrupt ATP production through several mechanisms. At the level of the citric acid cycle, arsenic inhibits pyruvate dehydrogenase and by competing with phosphate it uncouples oxidative phosphorylation, thus inhibiting energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is also increased, which might form reactive oxygen species and oxidative stress. Arsenic's carginogenicity is influenced by the arsenical binding of tubulin, which results in aneuploidy, polyploidy and mitotic arrests. The binding of other arsenic protein targets may also cause altered DNA repair enzyme activity, altered DNA methylation patterns and cell proliferation. (T1, A17) 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

3, 其对人类致癌性无法分类。

3, not classifiable as to its carcinogenicity to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

砒霜中毒可能导致多系统器官衰竭死亡，可能是由于细胞坏死而非凋亡。砒霜也是一种已知的致癌物，尤其是在皮肤癌、肝癌、膀胱癌和肺癌中。

Arsenic poisoning can lead to death from multi-system organ failure, probably from necrotic cell death, not apoptosis. Arsenic is also a known carcinogen, esepcially in skin, liver, bladder and lung cancers. (T1, L20)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L2）；吸入（L2）；皮肤（L2）

Oral (L2) ; inhalation (L2) ; dermal (L2)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

暴露在较低水平的砒霜下可能导致恶心和呕吐，减少红白细胞的生产，心律异常，血管损伤，以及一种感觉。

Exposure to lower levels of arsenic can cause nausea and vomiting, decreased production of red and white blood cells, abnormal heart rhythm, damage to blood vessels, and a sensation of

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  二苯基胂甲腈 在 双氧水 作用下， 生成 苯胺次胂酸
  参考文献：
  名称：

  Sturniolo; Bellinzoni, Gazzetta Chimica Italiana, 1919, vol. 49 II, p. 326

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯胂化氯 在 sodium hydroxide 作用下， 生成 二苯基胂甲腈
  参考文献：
  名称：

  McKenzie; Wood, Journal of the Chemical Society, 1920, vol. 117, p. 410

  摘要：

  DOI：

文献信息

• Steinkopf; Schwen, Chemische Berichte, 1921, vol. 54, p. 1452
  作者：Steinkopf、Schwen

  DOI：——

  日期：——
• Steinkopf; Schwen, Chemische Berichte, 1921, vol. 54, p. 2794,2796
  作者：Steinkopf、Schwen

  DOI：——

  日期：——
• Steinkopf; Donat; Jaeger, Chemische Berichte, 1922, vol. 55, p. 2610
  作者：Steinkopf、Donat、Jaeger

  DOI：——

  日期：——
• Morgan; Vining, Journal of the Chemical Society, 1920, vol. 117, p. 781
  作者：Morgan、Vining

  DOI：——

  日期：——
• Barker et al., Journal of the Society of Chemical Industry, 1949, vol. 68, p. 277
  作者：Barker et al.

  DOI：——

  日期：——