2,5-Dimethoxy-4-nitro-phenethylamine HCl | 874140-40-6

• 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: 2,5-Dimethoxy-4-nitro-phenethylamine HCl
• 英文别名: 2,5-Dimethoxy-4-nitrophenethylamine hydrochloride；2-(2,5-dimethoxy-4-nitrophenyl)ethanamine;hydrochloride
• CAS: 874140-40-6
• 化学式: C₁₀H₁₄N₂O₄*ClH
• 分子量: 262.693
• InChiKey: HBLKZKZKVLJMNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(18F)fluoranyl-2-methoxybenzaldehyde 、 2,5-Dimethoxy-4-nitro-phenethylamine HCl 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Convergent 18F-labeling and evaluation of N-benzyl-phenethylamines as 5-HT2A receptor PET ligands

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2016.08.056
• 作为产物：
  描述：

  2,5-二甲氧基-4-硝基苯乙胺 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 2,5-Dimethoxy-4-nitro-phenethylamine HCl
  参考文献：
  名称：

  [EN] SELECTIVE, PARTIAL, AND ARRESTIN-BIASED 5-HT2A AGONISTS WITH UTILITY IN VARIOUS DISORDERS
  [FR] AGONISTES SÉLECTIFS, PARTIELS ET POLARISÉS DE 5-HT2A AVEC UTILITÉ DANS DIVERS TROUBLES

  摘要：

  本文披露了一些新型的血清素5-HT2A受体激动剂，具有对其他血清素受体亚型的选择性。其中一些5-HT2A激动剂表现出功能选择性，优先激活阿雷斯汀信号转导而非G蛋白介导的信号转导。此外，还披露了这些化合物的制药组合物和治疗某些疾病或病症的方法。

  公开号：

  WO2022241006A1

文献信息

• Structure–Activity Assessment and In-Depth Analysis of Biased Agonism in a Set of Phenylalkylamine 5-HT_2A Receptor Agonists
  作者：Eline Pottie、Christian B. M. Poulie、Icaro A. Simon、Kasper Harpsøe、Laura D’Andrea、Igor V. Komarov、David E. Gloriam、Anders A. Jensen、Jesper L. Kristensen、Christophe P. Stove

  DOI：10.1021/acschemneuro.3c00267

  日期：2023.8.2

  as the preferential activation of certain signaling pathways over others. This study comparatively monitored the efficiency of a diverse panel of 4-position-substituted (and N-benzyl-derived) phenylalkylamines to induce recruitment of β-arrestin2 (βarr2) or miniGαq to the 5-HT2A, allowing us to assess structure–activity relationships and biased agonism. All test compounds exhibited agonist properties

  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
• 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.
• [EN] SELECTIVE, PARTIAL, AND ARRESTIN-BIASED 5-HT2A AGONISTS WITH UTILITY IN VARIOUS DISORDERS<br/>[FR] AGONISTES SÉLECTIFS, PARTIELS ET POLARISÉS DE 5-HT2A AVEC UTILITÉ DANS DIVERS TROUBLES
  申请人：SAINT JOSEPHS UNIV

  公开号：WO2022241006A1

  公开（公告）日：2022-11-17

  Disclosed herein are novel serotonin 5-HT2Areceptor agonists with selectivity for the 5-HT2Areceptor subtype over other serotonin receptors. Some of these 5-HT2Aagonists exhibit functional selectivity and preferentially activate arrestin signaling over G protein-mediated signaling. Also disclosed are pharmaceutical compositions of the compounds and methods of treating certain diseases or conditions.

  本文披露了一些新型的血清素5-HT2A受体激动剂，具有对其他血清素受体亚型的选择性。其中一些5-HT2A激动剂表现出功能选择性，优先激活阿雷斯汀信号转导而非G蛋白介导的信号转导。此外，还披露了这些化合物的制药组合物和治疗某些疾病或病症的方法。