(RS)-10-methoxy-9-methylaporphine | 754953-47-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: (RS)-10-methoxy-9-methylaporphine
• 英文别名: 10-methoxy-6,9-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
• CAS: 754953-47-4；778551-19-2；780729-64-8
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: UYESLAHJTLBEMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (RS)-10-methoxy-9-methylaporphine 在 氢溴酸 作用下， 反应 3.0h， 生成 (RS)-10-hydroxy-9-methylaporphine
  参考文献：
  名称：

  A-Ring Ortho-Disubstituted Aporphine Derivatives as Potential Agonists or Antagonists at Serotonergic 5-HT1A Receptors

  摘要：

  (R)- And (S)-11-hydroxy-10-methylaporphine 1 and 2 are, respectively, a potent, highly specific serotonergic (5-HT1A) agonist and antagonist. In an ongoing structure-activity study, racemates of the positional isomers 8-hydroxy-9-methyl- and 8-methyl-9-hydroxyaporphine were prepared by modifications of literature methods and were resolved. The methyl ethers of the target compounds were also evaluated pharmacologically. All of the free phenolic derivatives [(+)- and (-)-8 and 10] were inert in an assay for 5-HT1A receptor activity. All of the methyl ethers [(+)- and (-)-9 and 11] demonstrated quantitatively similar low potency stimulant effect at 5-HT1A receptors. The agonist or antagonist activity exhibited by 1 and 2 reflects the high degree of structural specificity required of aporphine derivatives for action at 5-HT1A receptors.

  DOI：

  10.1021/jm00011a002
• 作为产物：
  描述：

  2,4-二甲基-5-甲氧基硝基苯 、 N-methylisoquinolinium chloride 在 platinum(IV) oxide 硫酸 、 氢气 、 sodium ethanolate 、 铜 、 sodium nitrite 作用下， 生成 (RS)-10-methoxy-9-methylaporphine
  参考文献：
  名称：

  A-Ring Ortho-Disubstituted Aporphine Derivatives as Potential Agonists or Antagonists at Serotonergic 5-HT1A Receptors

  摘要：

  (R)- And (S)-11-hydroxy-10-methylaporphine 1 and 2 are, respectively, a potent, highly specific serotonergic (5-HT1A) agonist and antagonist. In an ongoing structure-activity study, racemates of the positional isomers 8-hydroxy-9-methyl- and 8-methyl-9-hydroxyaporphine were prepared by modifications of literature methods and were resolved. The methyl ethers of the target compounds were also evaluated pharmacologically. All of the free phenolic derivatives [(+)- and (-)-8 and 10] were inert in an assay for 5-HT1A receptor activity. All of the methyl ethers [(+)- and (-)-9 and 11] demonstrated quantitatively similar low potency stimulant effect at 5-HT1A receptors. The agonist or antagonist activity exhibited by 1 and 2 reflects the high degree of structural specificity required of aporphine derivatives for action at 5-HT1A receptors.

  DOI：

  10.1021/jm00011a002

文献信息

• A-Ring Ortho-Disubstituted Aporphine Derivatives as Potential Agonists or Antagonists at Serotonergic 5-HT1A Receptors
  作者：Joseph G. Cannon、Patrick T. Flaherty、Ugur Ozkutlu、John Paul Long

  DOI：10.1021/jm00011a002

  日期：1995.5

  (R)- And (S)-11-hydroxy-10-methylaporphine 1 and 2 are, respectively, a potent, highly specific serotonergic (5-HT1A) agonist and antagonist. In an ongoing structure-activity study, racemates of the positional isomers 8-hydroxy-9-methyl- and 8-methyl-9-hydroxyaporphine were prepared by modifications of literature methods and were resolved. The methyl ethers of the target compounds were also evaluated pharmacologically. All of the free phenolic derivatives [(+)- and (-)-8 and 10] were inert in an assay for 5-HT1A receptor activity. All of the methyl ethers [(+)- and (-)-9 and 11] demonstrated quantitatively similar low potency stimulant effect at 5-HT1A receptors. The agonist or antagonist activity exhibited by 1 and 2 reflects the high degree of structural specificity required of aporphine derivatives for action at 5-HT1A receptors.