4-氟-2,5-二甲氧基苯乙胺盐酸盐 | 1539266-59-5

• 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: 4-氟-2,5-二甲氧基苯乙胺盐酸盐
• 英文名称: 2-(4-fluoro-2,5-dimethoxyphenyl)ethan-1-amine hydrochloride
• 英文别名: 2,5-Dimethoxy-4-fluorophenethylamine hydrochloride；2-(4-fluoro-2,5-dimethoxyphenyl)ethanamine;hydrochloride
• CAS: 1539266-59-5
• 化学式: C₁₀H₁₄FNO₂*ClH
• 分子量: 235.686
• InChiKey: VQECHXCVFMXOPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 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：
  4

反应信息

• 作为反应物：
  描述：

  2,3-(亚甲二氧基)苯甲醛 、 4-氟-2,5-二甲氧基苯乙胺盐酸盐 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：

  1-fluoro-2,5-dimethoxy-4-(2-nitrovinyl)benzene 在 lithium aluminium tetrahydride 、 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 以79 %的产率得到4-氟-2,5-二甲氧基苯乙胺盐酸盐
  参考文献：
  名称：

  [EN] DIMETHOXYPHENYLALKYLAMINE ACTIVATORS OF SEROTONIN RECEPTORS
  [FR] ACTIVATEURS DE DIMÉTHOXYPHÉNYLALKYLAMINE DE RÉCEPTEURS DE LA SÉROTONINE

  摘要：

  Provided herein are compounds of Formula (I), or pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, R6, and n are defined herein. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I) or pharmaceutically acceptable salt thereof, and methods of using a compound of Formula (I) or pharmaceutically acceptable salt thereof, e.g., in the treatment of a mental health disease or disorder.

  公开号：

  WO2022261240A2

文献信息

• 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.
• [EN] DIMETHOXYPHENYLALKYLAMINE ACTIVATORS OF SEROTONIN RECEPTORS<br/>[FR] ACTIVATEURS DE DIMÉTHOXYPHÉNYLALKYLAMINE DE RÉCEPTEURS DE LA SÉROTONINE
  申请人：[en]ATAI LIFE SCIENCES AG

  公开号：WO2022261240A2

  公开（公告）日：2022-12-15

  Provided herein are compounds of Formula (I), or pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, R6, and n are defined herein. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I) or pharmaceutically acceptable salt thereof, and methods of using a compound of Formula (I) or pharmaceutically acceptable salt thereof, e.g., in the treatment of a mental health disease or disorder.