(R)-8-Methoxy-DPAT hydrochloride | 78095-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-8-Methoxy-DPAT hydrochloride
• 英文别名: (2R)-8-methoxy-N,N-dipropyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride
• CAS: 78095-31-5
• 化学式: C₁₇H₂₇NO*ClH
• 分子量: 297.868
• InChiKey: HPEKBNDAOQZJFF-XFULWGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  12.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-8-Methoxy-DPAT hydrochloride 在 氢溴酸 作用下， 以92%的产率得到(+)-8-OH-DPAT hydrochloride
  参考文献：
  名称：

  Resolved N,N-dialkylated 2-amino-8-hydroxytetralins: stereoselective interactions with 5-HT1A receptors in the brain

  摘要：

  The enantiomers of the N,N-dimethylamino (1), N,N-diethylamino (2), and N,N-dibutylamino (4) derivatives of 8-hydroxy-2-(dipropylamino)tetralin (8-OH DPAT; 3) have been synthesized. The compounds have been tested for activity at central 5-hydroxytryptamine and dopamine receptors by use of biochemical and behavioral tests in rats. In addition, the ability of the enantiomers of 1-4 to displace [3H]-8-OH DPAT from 5-HT1A binding sites was evaluated. Rank order of potencies in the in vivo tests corresponded to that observed in the 5-HT1A binding assay. In all three tests, the enantiomeric potency ratio was about 10 for 1 and 2 and only around 2-4 for 3 and 4. The more potent enantiomer of 1-3 had the R configuration. In contrast, (S)-4 seemed to be slightly more potent than (R)-4.

  DOI：

  10.1021/jm00124a009
• 作为产物：
  描述：

  1-碘代丙烷 、 (+)-(R)-2-amino-8-methoxytetralin hydrochloride 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以61%的产率得到(R)-8-Methoxy-DPAT hydrochloride
  参考文献：
  名称：

  Resolved N,N-dialkylated 2-amino-8-hydroxytetralins: stereoselective interactions with 5-HT1A receptors in the brain

  摘要：

  The enantiomers of the N,N-dimethylamino (1), N,N-diethylamino (2), and N,N-dibutylamino (4) derivatives of 8-hydroxy-2-(dipropylamino)tetralin (8-OH DPAT; 3) have been synthesized. The compounds have been tested for activity at central 5-hydroxytryptamine and dopamine receptors by use of biochemical and behavioral tests in rats. In addition, the ability of the enantiomers of 1-4 to displace [3H]-8-OH DPAT from 5-HT1A binding sites was evaluated. Rank order of potencies in the in vivo tests corresponded to that observed in the 5-HT1A binding assay. In all three tests, the enantiomeric potency ratio was about 10 for 1 and 2 and only around 2-4 for 3 and 4. The more potent enantiomer of 1-3 had the R configuration. In contrast, (S)-4 seemed to be slightly more potent than (R)-4.

  DOI：

  10.1021/jm00124a009

文献信息

• BJORK, LENA;HOOK, BERIT BACKLUND;NELSON, DAVID L.;ANDEN, NILS-ERIK;HACKSE+, J. MED. CHEM., 32,(1989) N, C. 779-783
  作者：BJORK, LENA、HOOK, BERIT BACKLUND、NELSON, DAVID L.、ANDEN, NILS-ERIK、HACKSE+

  DOI：——

  日期：——