2-[[2-[2,5-Dimethoxy-4-(trifluoromethyl)phenyl]ethylamino]methyl]phenol | 1025934-95-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: 2-[[2-[2,5-Dimethoxy-4-(trifluoromethyl)phenyl]ethylamino]methyl]phenol
• CAS: 1025934-95-5
• 化学式: C₁₈H₂₀F₃NO₃
• 分子量: 355.357
• InChiKey: SUMTWXSRGZRXOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 2-[[2-[2,5-Dimethoxy-4-(trifluoromethyl)phenyl]ethylamino]methyl]phenol
  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

文献信息

• [EN] PHENALKYLAMINES AND METHODS OF TREATING MOOD DISORDERS<br/>[FR] PHÉNALKYLAMINES ET PROCÉDÉS DE TRAITEMENT DE TROUBLES DE L'HUMEUR
  申请人：GILGAMESH PHARMACEUTICALS INC

  公开号：WO2022006186A1

  公开（公告）日：2022-01-06

  Phenalkylamines and methods of treating mood disorders with phenalkylamines. Also provided are pharmaceutical compositions that include phenalkylamines.

  Phenalkylamines和使用Phenalkylamines治疗情绪障碍的方法。还提供了包含Phenalkylamines的制药组合物。