ethylthioninium chloride | 108602-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: ethylthioninium chloride
• 英文别名: 7-(Diethylamino)-N,N-diethyl-3H-phenothiazin-3-iminium chloride；[7-(diethylamino)phenothiazin-3-ylidene]-diethylazanium;chloride
• CAS: 108602-20-6
• 化学式: C₂₀H₂₆N₃S*Cl
• 分子量: 375.966
• InChiKey: MSNQIUOPQJJQNU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N-二乙基对苯二胺盐酸盐 在 盐酸 、 sodium sulfide 、 iron(III) chloride 作用下， 以 水 为溶剂， 反应 1.0h， 生成 ethylthioninium chloride
  参考文献：
  名称：

  [EN] METHODS OF CHEMICAL SYNTHESIS AND PURIFICATION OF DIAMINOPHENOTHIAZINIUM COMPOUNDS INCLUDING METHYLTHIONINIUM CHLORIDE (MTC)
  [FR] PROCEDES DE SYNTHESE CHIMIQUE ET DE PURIFICATION DE COMPOSES DIAMINOPHENOTHIAZINIUM RENFERMANT DU CHLORURE DE METHYLTHIONINIUM (MTC)

  摘要：

  公开号：

  WO2006032879A3

文献信息

• Supramolecular binding and release of sulfide and hydrosulfide anions in water
  作者：J. Vázquez、V. Sindelar

  DOI：10.1039/c8cc00470f

  日期：——

  Bambusuril macrocycles bind and release sulfide and hydrosulfide anions in water.

  竹葡萄糖大环在水中结合并释放硫化物和氢硫化物阴离子。
• Thioninium compounds and their use
  申请人：WisTa Laboratories Ltd.

  公开号：EP2853293B1

  公开（公告）日：2017-11-22
• WO2007/110629
  申请人：——

  公开号：——

  公开（公告）日：——
• Azure B and a synthetic structural analogue of methylene blue, ethylthioninium chloride, present with antidepressant-like properties
  作者：Anzelle Delport、Brian H. Harvey、Anél Petzer、Jacobus P. Petzer

  DOI：10.1016/j.lfs.2014.10.005

  日期：2014.11

  Aims: The phenothiazinium compound, methylene blue (MB), possesses diverse pharmacological actions and is attracting attention for the treatment of bipolar disorder and Alzheimer's disease. MB acts on both monoamine oxidase (MAO) and the nitric oxide (NO)-cGMP pathway, and possesses antidepressant activity in rodents. The goal of this study was to synthesise a structural analogue of MB, ethylthioninium chloride (ETC), and to evaluate the effects of the structural changes on the MAO inhibitory and antidepressant properties of MB. This study also investigated the antidepressant properties of azure B, the major metabolite of MB, versus MB and imipramine as active comparators.Main methods: ETC and azure B were firstly evaluated as inhibitors of human MAO, and secondly for antidepressant-like activity in the acute forced swim test (FST) in rats, and compared to saline, imipramine and MB.Key findings: The results document that ETC is a reversible inhibitor of MAO-A and MAO-B with IC50 values of 0.510 mu M and 0.592 mu M, respectively, and that it is a weaker MAO-A inhibitor than MB and azure B. ETC and azure B were more effective than imipramine and MB in reversing immobility in the FST without inducing locomotor effects, with evidence supporting a serotonergic action. Of interest is the finding that ETC is more toxic for cultured cells than MB.Conclusion: Azure B may therefore be a contributor to the antidepressant effect of MB. Small structural changes made to MB retain its antidepressant effect, even though the resulting phenothiazinium compound possesses reduced MAO-A inhibitory potency. (C) 2014 Elsevier Inc. All rights reserved.