4-(2-aminoethyl)-2,5-dimethoxybenzonitrile | 88441-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-aminoethyl)-2,5-dimethoxybenzonitrile
• 英文别名: 2,5-Dimethoxy-4-cyanophenethylamine
• CAS: 88441-07-0
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: OGWCKYKYGQORLF-UHFFFAOYSA-N

物化性质

• 沸点：
  367.5±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-aminoethyl)-2,5-dimethoxybenzonitrile 在 sodium hydroxide 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 4-(2-氨基乙基)-2,5-二羟基苯甲酸
  参考文献：
  名称：

  Synthesis and physicochemical and neurotoxicity studies of 1-(4-substituted-2,5-dihydroxyphenyl)-2-aminoethane analogs of 6-hydroxydopamine

  摘要：

  In an attempt to evaluate the possible relationship between the neurotoxicity of 6-hydroxydopamine and the redox properties and electrophilic reactivity of the 6-hydroxydopamine-p-hydroquinone/p-quinone system, we have synthesized a series of 6-hydroxydopamine analogues in which the C4-hydroxy group is replaced with various electron-donating and electron-withdrawing substituents. With the aid of cyclic voltammetry, the formal oxidation potentials (E degrees ') for the p-hydroquinone/p-quinone redox couples and the rates of cyclization of the p-quinones to the corresponding p-iminoquinones were determined. As expected, electron-rich p-hydroquinones were easily oxidized to the p-quinones, which underwent cyclization slowly, whereas the oxidation of electron-poor p-hydroquinones required higher voltages and yielded p-quinones, which cyclized readily at pH 7.4. The neurotoxic potential of these compounds showed that in vivo destruction of noradrenergic terminals, as measured by inhibition of norepinephrine uptake by rat heart slices, occurred only with those analogues bearing electron-donating substituents. Potent neurotoxic properties were associated only with the 4-amino and 4-hydroxy derivatives, both of which form p-quinones, which do not cyclize readily at pH 7.4. These results support the thesis that the p-quinone derived from 6-hydroxydopamine may be an important species in the mediation of the neurodestruction caused by 6-hydrodopamine.

  DOI：

  10.1021/jm00370a014
• 作为产物：
  描述：

  4-溴-2,5二甲氧基苯乙胺 在 肼 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 4-(2-aminoethyl)-2,5-dimethoxybenzonitrile
  参考文献：
  名称：

  一组苯烷基胺 5-HT2A 受体激动剂的偏向激动的结构-活性评估和深入分析

  摘要：

  据描述，血清素能致幻剂的主要药理作用是激活血清素 2A 受体 (5-HT 2A )。尽管它们具有相关性，但某些 5-HT 2A激动剂引起迷幻作用的分子机制仍然难以捉摸。提出的假设之一是偏向激动的发生，其定义为某些信号通路相对于其他信号通路的优先激活。这项研究比较监测了一组不同的 4 位取代（和N-苄基衍生的）苯基烷基胺诱导 β-arrestin2 (βarr2) 或 miniGα q募集到 5-HT 2A的效率，使我们能够评估结构–活动关系和偏激性。所有测试化合物均表现出激动剂特性，EC 50和E max值范围相对较大。有趣的是，2C-X 苯乙胺的亲脂性与其在两种测定中的功效相关，但在 miniGα q中产生的相关性比在 βarr2 测定中更强。分子对接表明，2C-X 类似物的 4-取代基容纳在 5-HT 2A 跨膜螺旋 4 和 5 之间的疏水袋中可能有助于这种差异效应。除了以前使用的标准条件（麦角酸二乙酰胺

  DOI：

  10.1021/acschemneuro.3c00267

文献信息

• [EN] PHENALKYLAMINES AND METHODS OF MAKING AND USING THE SAME<br/>[FR] PHÉNALKYLAMINES ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：GILGAMESH PHARMACEUTICALS INC

  公开号：WO2022192781A1

  公开（公告）日：2022-09-15

  The present disclosure provides phenalkylamine compounds and their use in treating medical disorders, such as psychiatric diseases and disorders. Pharmaceutical compositions and methods of making various phenalkylamine compounds are provided.

  本公开提供了苯基烷胺化合物及其在治疗医学疾病（如精神科疾病和障碍）中的应用。提供了制备各种苯基烷胺化合物的制药组合物和方法。
• Immunoassay for phenethylamines of the 2C and DO sub-families
  申请人：Randox Laboratories Limited

  公开号：US10775394B2

  公开（公告）日：2020-09-15

  Immunoassay methods and their requisite components for the detection and determination of phenethylamines of the 2C and DO sub-families are described.

  介绍了用于检测和测定 2C 和 DO 亚家族苯乙胺的免疫测定方法及其必要成分。
• Convergent 18F-labeling and evaluation of N-benzyl-phenethylamines as 5-HT2A receptor PET ligands
  作者：Ida Nymann Petersen、Jonas Villadsen、Hanne Demant Hansen、Anders A. Jensen、Szabolcs Lehel、Nic Gillings、Matthias M. Herth、Gitte M. Knudsen、Jesper L. Kristensen

  DOI：10.1016/j.bmc.2016.08.056

  日期：2016.11

  Positron emission tomography (PET) investigations of the 5-HT2A receptor (5-HT2AR) system can be used as a research tool in diseases such as depression, Alzheimer's disease and schizophrenia. We have previously developed a C-11-labeled agonist PET ligand ([C-11]Cimbi-36), and the aim of this study was to identify a F-18-labeled analogue of this PET-ligand. Thus, we developed a convergent radiochemical approach giving easy access to 5 different F-18-labeled ligands structurally related to Cimbi-36 from a common F-18-labeled intermediate. After intravenous injection, all ligands entered the pig brain. However, since within-scan intervention with ketanserin, a known orthosteric 5-HT2A receptor antagonist, did not result in significant blocking, the radioligands seem unsuitable for neuroimaging of the 5-HT2AR in vivo. (C) 2016 Elsevier Ltd. All rights reserved.
• Immunoassay for Phenethylamines of the 2C and DO Sub-Families
  申请人：Randox Laboratories Ltd.

  公开号：EP2835648B1

  公开（公告）日：2018-12-12
• IMMUNOASSAY FOR PHENETHYLAMINES OF THE 2C AND DO SUB-FAMILIES
  申请人：Randox Laboratories Limited

  公开号：US20180209998A1

  公开（公告）日：2018-07-26

  Immunoassay methods and their requisite components for the detection and determination of phenethylamines of the 2C and DO sub-families are described.