(RS)-1-<2-amino-5-(benzyloxy)-4-methoxybenzyl>-2-methyl-1,2,3,4-tetrahydroisoquinoline dihydrochloride | 131792-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (RS)-1-<2-amino-5-(benzyloxy)-4-methoxybenzyl>-2-methyl-1,2,3,4-tetrahydroisoquinoline dihydrochloride
• CAS: 131792-50-2
• 化学式: C₂₅H₂₈N₂O₂*2ClH
• 分子量: 461.431
• InChiKey: SEWMBJGOPNFQAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  47.72
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (RS)-1-<2-amino-5-(benzyloxy)-4-methoxybenzyl>-2-methyl-1,2,3,4-tetrahydroisoquinoline dihydrochloride 在 palladium on activated charcoal sodium hydroxide 、 硫酸 、 氢气 、 铜 、 sodium nitrite 作用下， 以 乙醇 为溶剂， -5.0~25.0 ℃ 、310.27 kPa 条件下， 反应 30.25h， 生成 (RS)-9-hydroxy-10-methoxyaporphine hydrochloride
  参考文献：
  名称：

  Isomeric monomethyl ether derivatives of (RS)-9,10-dihydroxyaporphine ("isoapomorphine") as possible products of metabolism by catechol-O-methyltransferase

  摘要：

  The isomeric monomethyl ether derivatives of (RS)-9,10-dihydroxyaporphine (''isoapomorphine'') were synthesized unequivocally as possible metabolites in catechol-O-methyltransferase (COMT) mediated O-methylation reactions. In vitro incubation studies revealed that isoapomorphine is not a substrate for the COMT using experimental conditions under which apomorphine (10,11-dihydroxyaporphine) is converted in high yield into its 10-methyl ether, apocodeine. The in vivo dopaminergic inactivity of isoapomorphine (as compared with that of apomorphine) seems to be due to factors other than metabolic inactivation by COMT.

  DOI：

  10.1021/jm00107a030
• 作为产物：
  描述：

  5-(benzyloxy)-4-methoxy-2-nitrotoluene 在 palladium on activated charcoal 盐酸 、 乙醇 、 氢气 、 sodium 、 溶剂黄146 作用下， 50.0~78.0 ℃ 、310.27 kPa 条件下， 反应 0.17h， 生成 (RS)-1-<2-amino-5-(benzyloxy)-4-methoxybenzyl>-2-methyl-1,2,3,4-tetrahydroisoquinoline dihydrochloride
  参考文献：
  名称：

  Isomeric monomethyl ether derivatives of (RS)-9,10-dihydroxyaporphine ("isoapomorphine") as possible products of metabolism by catechol-O-methyltransferase

  摘要：

  The isomeric monomethyl ether derivatives of (RS)-9,10-dihydroxyaporphine (''isoapomorphine'') were synthesized unequivocally as possible metabolites in catechol-O-methyltransferase (COMT) mediated O-methylation reactions. In vitro incubation studies revealed that isoapomorphine is not a substrate for the COMT using experimental conditions under which apomorphine (10,11-dihydroxyaporphine) is converted in high yield into its 10-methyl ether, apocodeine. The in vivo dopaminergic inactivity of isoapomorphine (as compared with that of apomorphine) seems to be due to factors other than metabolic inactivation by COMT.

  DOI：

  10.1021/jm00107a030