2,5-二甲氧基-4-氯苯乙胺盐酸盐 | 88441-15-0

• 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: 2,5-二甲氧基-4-氯苯乙胺盐酸盐
• 中文别名: 2-(4-氯-2,5-二甲氧基苯基)乙胺盐酸盐
• 英文名称: 1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane hydrochloride
• 英文别名: 2-(4-chloro-2,5-dimethoxyphenyl)ethanamine hydrochloride；4-chloro-2,5-dimethoxyphenylethylamine hydrochloride；2,5-dimethoxy-4-chlorophenethylamine hydrochloride；2C-C；4-Chloro-2,5-dimethoxyphenethylamine hydrochloride；2-(4-chloro-2,5-dimethoxyphenyl)ethanamine;hydrochloride
• CAS: 88441-15-0
• 化学式: C₁₀H₁₄ClNO₂*ClH
• 分子量: 252.141
• InChiKey: BKHKVQPFRTVWJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-(亚甲二氧基)苯甲醛 、 2,5-二甲氧基-4-氯苯乙胺盐酸盐 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of N-Benzyl Phenethylamines as 5-HT_2A/2C Agonists

  摘要：

  N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5-dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule to determine the effects on receptor binding affinity and functional activity at 5-HT2A and 5-HT2c receptors. The compounds generally had high affinity for the 5-HT2A receptor with 8b having the highest affinity at 0.29 nM but with several other compounds also exhibiting subnanomolar binding affinities. The functional activity of the compounds was distributed over a wider range with lb being the most potent at 0.074 nM. Most of the compounds exhibited low to moderate selectivity (1- to 40-fold) for the 5-HT2A receptor in the binding assays, although one compound 6b showed an impressive 100-fold selectivity for the 5-HT2A receptor. In the functional assay, selectivity was generally higher with lb being more than 400-fold selective for the 5-HT2A receptor.

  DOI：

  10.1021/cn400216u
• 作为产物：
  描述：

  2,5-二甲氧基苯乙胺 在 磺酰氯 、 溶剂黄146 作用下， 反应 3.0h， 生成 2,5-二甲氧基-4-氯苯乙胺盐酸盐
  参考文献：
  名称：

  氘标记苯乙胺衍生物的合成

  摘要：

  一系列五种氘标记的苯乙胺衍生物的合成，4-溴-2,5-[2H6]-二甲氧基苯乙胺（2C-B），4-氯-2,5-[2H6]-二甲氧基苯乙胺（2C-C）， 2,5-[2H6]-二甲氧基-4-碘苯乙胺 (2C-I)、2,5-[2H6]-二甲氧基-4-乙基噻吩乙胺 (2C-T-2) 和 2,5-[2H6]-二甲氧基-描述了来自 1,4-[2H6]-二甲氧基苯的 4-n-丙基噻吩乙胺 (2C-T-7)。同位素标记的化合物用作气相色谱-质谱 (GC-MS) 分析中的内标。版权所有 © 2006 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1139

文献信息

• 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.
• Synthesis of deuterium labeled phenethylamine derivatives
  作者：Ya-Zhu Xu、Chinpiao Chen

  DOI：10.1002/jlcr.1139

  日期：2006.11

  The synthesis of a series of five deuterium labeled phenethylamine derivatives, 4-bromo-2,5-[2H6]-dimethoxyphenethylamine (2C-B), 4-chloro-2,5-[2H6]-dimethoxyphenethylamine (2C-C), 2,5-[2H6]-dimethoxy-4-iodophenethylamine (2C-I), 2,5-[2H6]-dimethoxy-4-ethylthiophenethylamine (2C-T-2) and 2,5-[2H6]-dimethoxy-4-n-propylthiophenethylamine (2C-T-7) from 1,4-[2H6]-dimethoxybenzene is described. The isotopically

  一系列五种氘标记的苯乙胺衍生物的合成，4-溴-2,5-[2H6]-二甲氧基苯乙胺（2C-B），4-氯-2,5-[2H6]-二甲氧基苯乙胺（2C-C）， 2,5-[2H6]-二甲氧基-4-碘苯乙胺 (2C-I)、2,5-[2H6]-二甲氧基-4-乙基噻吩乙胺 (2C-T-2) 和 2,5-[2H6]-二甲氧基-描述了来自 1,4-[2H6]-二甲氧基苯的 4-n-丙基噻吩乙胺 (2C-T-7)。同位素标记的化合物用作气相色谱-质谱 (GC-MS) 分析中的内标。版权所有 © 2006 John Wiley & Sons, Ltd.
• Synthesis and Structure–Activity Relationships of <i>N</i>-Benzyl Phenethylamines as 5-HT_2A/2C Agonists
  作者：Martin Hansen、Karina Phonekeo、James S. Paine、Sebastian Leth-Petersen、Mikael Begtrup、Hans Bräuner-Osborne、Jesper L. Kristensen

  DOI：10.1021/cn400216u

  日期：2014.3.19

  N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5-dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule to determine the effects on receptor binding affinity and functional activity at 5-HT2A and 5-HT2c receptors. The compounds generally had high affinity for the 5-HT2A receptor with 8b having the highest affinity at 0.29 nM but with several other compounds also exhibiting subnanomolar binding affinities. The functional activity of the compounds was distributed over a wider range with lb being the most potent at 0.074 nM. Most of the compounds exhibited low to moderate selectivity (1- to 40-fold) for the 5-HT2A receptor in the binding assays, although one compound 6b showed an impressive 100-fold selectivity for the 5-HT2A receptor. In the functional assay, selectivity was generally higher with lb being more than 400-fold selective for the 5-HT2A receptor.