2-羟基乙基-三甲基鉮 | 39895-81-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 2-羟基乙基-三甲基鉮
• 英文名称: arsenocholine
• 英文别名: 2-hydroxyethyl(trimethyl)arsanium
• CAS: 39895-81-3
• 化学式: C₅H₁₄AsO
• 分子量: 165.087
• InChiKey: ORLOBEXOFQEWFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

砷主要通过吸入或摄入进入人体，其次是皮肤接触。进入人体后，砷会在全身分布，根据需要被还原成亚砷酸盐，然后通过亚砷酸盐甲基转移酶被甲基化成单甲基砷（MMA）和二甲基硅酸（DMA）。砷及其代谢物主要通过尿液排出体外。已知砷能诱导金属结合蛋白金属硫蛋白，金属硫蛋白通过结合砷和其他金属，使它们生物学上失活，并作为抗氧化剂，从而减少砷和其他金属的有毒效果。

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)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

砒霜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，砒霜抑制了丙酮酸脱氢酶，并通过与磷酸竞争解耦了氧化磷酸化，从而抑制了与能量相关的NAD+还原、线粒体呼吸和ATP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。砒霜的致癌性受到砒霜与微管蛋白结合的影响，导致非整倍体、多倍体和有丝分裂停滞。其他砒霜蛋白靶点的结合也可能导致DNA修复酶活性改变、DNA甲基化模式改变和细胞增殖。

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)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

3, 无法归类其对人类致癌性的类别。(L135)

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）；皮肤给药（L2）

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

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

暴露于较低水平的砷可以导致恶心和呕吐，减少红白细胞的生产，心律异常，血管损伤和烧灼感。

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 burn (T1).

来源:Toxin and Toxin Target Database (T3DB)

反应信息

• 作为反应物：
  描述：

  2-羟基乙基-三甲基鉮 、 1,2-二油酰基-sn-甘油-3-磷酸胆碱 在 acetate buffer 、 calcium chloride 作用下， 以 乙醚 、 水 为溶剂， 反应 7.0h， 以78%的产率得到
  参考文献：
  名称：

  Enzymatic introduction of N-heterocyclic and As-containing head groups into glycerophospholipids

  摘要：

  The synthesis of six new glycerophospholipids with choline-analogous head groups by enzymatic transphosphatidylation with phospholipase D is described. Starting from 1,2-dioleoyl-sn-glycero-3-phosphocholine primary or secondary N-heterocyclic alcohols and (2-hydroxyethyl) trimethylarsonium were substituted for choline in two-phase systems. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00082-8
• 作为产物：
  描述：

  在 phosphate buffer 作用下， 以 水 为溶剂， 以100%的产率得到2-羟基乙基-三甲基鉮
  参考文献：
  名称：

  1-（邻硝基苯基）-2,2,2-三氟乙基醚衍生物作为稳定和有效的可光除去的醇保护基团。

  摘要：

  DOI：

  10.1002/anie.200353247