(+/-)-1-(2,5-dimethoxy-3-methylphenyl)-2-aminopropane | 72739-20-9

• 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: (+/-)-1-(2,5-dimethoxy-3-methylphenyl)-2-aminopropane
• 英文别名: 1-(2,5-Dimethoxy-3-methylphenyl)propan-2-amine
• CAS: 72739-20-9
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: XZYCPUFGPVSHSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,5-dimethoxy-3-methylbenzaldehyde 在 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 乙醚 为溶剂， 反应 11.0h， 生成 (+/-)-1-(2,5-dimethoxy-3-methylphenyl)-2-aminopropane
  参考文献：
  名称：

  Serotonin receptor affinities of psychoactive phenalkylamine analogs

  摘要：

  Employing a rat fundus model, the serotonin (5-HT) receptor affinities of 45 phenalkylamine analogues were determined. Phenethylamine and phenylisopropylamine possess relatively low receptor affinities; in general, mono-, di-, and trimethoxylation enhance affinity. Of the disubstituted compounds, methoxyl groups at the 2 and 5 positions are optimal for imparting a high affinity. 4-Methylation, 4-ethylation and 4-bromination also enhance receptor affinity, while N,N-dimethylation of the terminal amine decreases affinity. alpha-Methylation of phenethylamines has little effect on affinity when racemates are examined. Introduction of a benzylic keto group can either increase or decrease affinity, depending upon the presence of other aromatic substituents. The most behaviorally active compounds were found to possess the highest 5-HT receptor affinities, while less active compounds were found to possess lower affinities.

  DOI：

  10.1021/jm00177a017

文献信息

• GLENNON R. A.; LIEBOWITZ S. M.; ANDERSON III G. M., J. MED. CHEM., 1980, 23, NO 3, 294-299
  作者：GLENNON R. A.、 LIEBOWITZ S. M.、 ANDERSON III G. M.

  DOI：——

  日期：——
• IMPROVED METHODS OF AND COMPOSITIONS FOR THE PREVENTION OF ANXIETY, SUBSTANCE ABUSE, AND DEPENDENCE
  申请人：Hythiam, Inc.

  公开号：EP1868593A2

  公开（公告）日：2007-12-26
• [EN] IMPROVED METHODS OF AND COMPOSITIONS FOR THE PREVENTION OF ANXIETY, SUBSTANCE ABUSE, AND DEPENDENCE<br/>[FR] PROCEDES AMELIORES ET COMPOSITIONS PERMETTANT DE PREVENIR L'ANXIETE, L'ABUS D'UNE SUBSTANCE ET LA DEPENDANCE
  申请人：HYTHIAM INC

  公开号：WO2006110642A2

  公开（公告）日：2006-10-19

  [EN] Compositions for reducing dependency and addiction to substances of abuse are provided. Chloride channels such as the GABA_A receptors are altered under conditions of dependency and withdrawal such that the electrophysiological properties of the GABA_A receptor containing neurons are altered thereby providing a pathophysiological condition resulting in symptoms of dependency and withdrawal such as anxiety. Specifically, under conditions of withdrawal the relative ratio of the a1 receptor subunit decreases relative to the a4 receptor subunit. Endogenous neurosteroid production is also associated with the molecular changes underlying the alterations of GABA-gated chloride channels. Compositions of at least two compounds including at least one inhibitor of neurosteroid production are useful for treating the pathophysiology of addiction, dependency and substance abuse withdrawal.
  [FR] L'invention concerne des compositions permettant de limiter la dépendance et l'addiction à des substances donnant lieu à des abus. Les canaux chlorure, tels que les récepteurs GABA_A, sont modifiés dans des conditions de dépendance et de sevrage de sorte que les propriétés électrophysiologiques des neurones contenant le récepteur GABA_A sont modifiées, ce qui produit un état pathophysiologique résultant en symptômes de dépendance et de sevrage tel que l'anxiété. De manière spécifique, dans des conditions de sevrage, le rapport relatif de la sous-unité du récepteur a1 décroît par rapport à la sous-unité du récepteur a4. La production de neurostéroïdes endogènes est également associée aux changements moléculaires entraînant les altérations des canaux chlorure à grille GABA. On utilise des compositions d'au moins deux composés comprenant au moins un inhibiteur de production de neurostéroïdes pour traiter la pathophysiologie de l'addiction, de la dépendance et du sevrage de toxicomanie.
• Serotonin receptor affinities of psychoactive phenalkylamine analogs
  作者：Richard A. Glennon、Stephen M. Liebowitz、George M. Anderson

  DOI：10.1021/jm00177a017

  日期：1980.3

  Employing a rat fundus model, the serotonin (5-HT) receptor affinities of 45 phenalkylamine analogues were determined. Phenethylamine and phenylisopropylamine possess relatively low receptor affinities; in general, mono-, di-, and trimethoxylation enhance affinity. Of the disubstituted compounds, methoxyl groups at the 2 and 5 positions are optimal for imparting a high affinity. 4-Methylation, 4-ethylation and 4-bromination also enhance receptor affinity, while N,N-dimethylation of the terminal amine decreases affinity. alpha-Methylation of phenethylamines has little effect on affinity when racemates are examined. Introduction of a benzylic keto group can either increase or decrease affinity, depending upon the presence of other aromatic substituents. The most behaviorally active compounds were found to possess the highest 5-HT receptor affinities, while less active compounds were found to possess lower affinities.