2-(2,5-dimethoxy-4-(methylthio)phenyl)ethan-1-amine hydrochloride | 61638-10-6

• 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-(2,5-dimethoxy-4-(methylthio)phenyl)ethan-1-amine hydrochloride
• 英文别名: 2,5-Dimethoxy-4-methylthiophenethylamine hydrochloride；2-(2,5-dimethoxy-4-methylsulfanylphenyl)ethanamine;hydrochloride
• CAS: 61638-10-6
• 化学式: C₁₁H₁₇NO₂S*ClH
• 分子量: 263.788
• InChiKey: LMLQBDIAGNIIJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  69.8
• 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 、 2-(2,5-dimethoxy-4-(methylthio)phenyl)ethan-1-amine hydrochloride 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：

  1,4-dimethoxy-2-methylsulfanyl-5-[(E)-2-nitroethenyl]benzene 在 锂硼氢 、 三甲基氯硅烷 、 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 以83 %的产率得到2-(2,5-dimethoxy-4-(methylthio)phenyl)ethan-1-amine hydrochloride
  参考文献：
  名称：

  NOVEL SULFOXIMINE ACTIVATORS OF SEROTONIN RECEPTORS

  摘要：

  Methods of treating a stress-related disease or disorder such as PTSD and mood/depressive disorder, inducing neurite outgrowth, or inducing structural neuroplasticity, comprising administering to a subject a composition comprising an effective amount of a compound that does not have an agonist activity on 5-HT2Aserotonin receptor are disclosed. Also disclosed are pharmaceutical compositions comprising compound not having an agonist activity on 5-HT2Aserotonin receptor and a pharmaceutically acceptable carrier.

  公开号：

  WO2024124056A1