(1R,2S)-5-甲氧基-1-甲基-N,N-二丙基-2-四氢萘胺 | 95999-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: (1R,2S)-5-甲氧基-1-甲基-N,N-二丙基-2-四氢萘胺
• 英文名称: (1R,2S)-cis-5-methoxy-1-methyl-2-(di-n-propylamino)tetralin
• 英文别名: (-)-UH 232；cis-5-Methoxy-1-methyl-2-(di-n-propylamino)tetralin；(1R,2S)-5-methoxy-1-methyl-N,N-dipropyl-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 95999-11-4
• 化学式: C₁₈H₂₉NO
• 分子量: 275.434
• InChiKey: BTOJYCTUJJHANF-PBHICJAKSA-N

物化性质

• 熔点：
  160.5-161.0 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
• 沸点：
  379.7±42.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  (1R,2S)-5-甲氧基-1-甲基-N,N-二丙基-2-四氢萘胺 、 水 、 盐酸 、 氢溴酸 以88%的产率得到
  参考文献：
  名称：

  JOHANSSON, A. M.;ARVIDSSON, L. -E.;HACKSELL, U.;NILSSON, J. L. G.;SVENSSO+, J. MED. CHEM., 1985, 28, N 8, 1049-1053

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-cis-5-methoxy-1-methyl-2-<(1-phenylethyl)amino>tetralin hydrochloride 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 240.0h， 生成 (1R,2S)-5-甲氧基-1-甲基-N,N-二丙基-2-四氢萘胺
  参考文献：
  名称：

  Novel dopamine receptor agonists and antagonists with preferential action on autoreceptors

  摘要：

  The enantiomers of cis-5-hydroxy-1-methyl-2-(di-n-propylamino)tetralin and its methyl ether have been synthesized. The compounds were tested for central dopamine (DA) receptor activity, by using biochemical and behavioral tests in rats. The (1R,2S)-(-) enantiomers of 1 and 2 are characterized as centrally acting DA-receptor agonists while the corresponding (1S,2R)-(+) enantiomers are characterized as centrally acting DA-receptor antagonists. Compounds (+)-1 and (+)-2 differ from classical neuroleptics in being able to increase DA synthesis rate in a wide dose range without reducing locomotor activity, suggesting a pronounced selectivity for DA autoreceptors. Also the (-) enantiomers seem to act preferentially on DA autoreceptors.

  DOI：

  10.1021/jm00146a012

文献信息

• Resolved cis- and trans-2-amino-5-methoxy-1-methyltetralins: central dopamine receptor agonists and antagonists
  作者：Anette M. Johansson、Lars Erik Arvidsson、Uli Hacksell、J. Lars G. Nilsson、Kjell Svensson、Arvid Carlsson

  DOI：10.1021/jm00387a004

  日期：1987.4

  A series of 35 stereochemically well-defined C1-methyl-substituted derivatives of the potent dopamine (DA) receptor agonist 5-hydroxy-2-(di-n-propylamino)tetralin (5-OH-DPAT) have been synthesized. The compounds were tested for central DA receptor agonistic and antagonistic activity, by use of biochemical and behavioral tests in rats. In addition, the compounds were tested for in vivo interactions with 5,6-dihydroxy-2-(di-n-propylamino)tetralin (DiPr-5,6-ADTN). On the basis of pharmacological activity profiles, the active compounds have been classified into four groups: classical pre- and postsynaptic DA receptor agonists, DA receptor agonists with preferential action at presynaptic receptors, pre- and postsynaptic DA receptor antagonists, and DA receptor antagonists with preferential action at presynaptic receptors. Results obtained indicate that both 2R and 2S enantiomers of C5-oxygenated 2-aminotetralins may be able to bind to DA receptors but that only 2S antipodes are able to activate the receptors. O-Methylation of the C5-oxygenated (1S,2R)-2-amino-1-methyltetralin derivatives tends to increase their DA receptor antagonistic activity, whereas decrease of the size of the N-substituent(s) from n-propyl to ethyl or methyl appears to increase their activity at postsynaptic DA receptors.
• Novel dopamine receptor agonists and antagonists with preferential action on autoreceptors
  作者：Anette M. Johansson、Lars Erik Arvidsson、Uli Hacksell、J. Lars G. Nilsson、Kjell Svensson、Stephan Hjorth、David Clark、Arvid Carlsson、Domingo Sanchez

  DOI：10.1021/jm00146a012

  日期：1985.8

  The enantiomers of cis-5-hydroxy-1-methyl-2-(di-n-propylamino)tetralin and its methyl ether have been synthesized. The compounds were tested for central dopamine (DA) receptor activity, by using biochemical and behavioral tests in rats. The (1R,2S)-(-) enantiomers of 1 and 2 are characterized as centrally acting DA-receptor agonists while the corresponding (1S,2R)-(+) enantiomers are characterized as centrally acting DA-receptor antagonists. Compounds (+)-1 and (+)-2 differ from classical neuroleptics in being able to increase DA synthesis rate in a wide dose range without reducing locomotor activity, suggesting a pronounced selectivity for DA autoreceptors. Also the (-) enantiomers seem to act preferentially on DA autoreceptors.
• JOHANSSON, A. M.;ARVIDSSON, L. -E.;HACKSELL, U.;NILSSON, J. L. G.;SVENSSO+, J. MED. CHEM., 1985, 28, N 8, 1049-1053
  作者：JOHANSSON, A. M.、ARVIDSSON, L. -E.、HACKSELL, U.、NILSSON, J. L. G.、SVENSSO+

  DOI：——

  日期：——