4,5-(methylenedioxy)-2-aminoindan | 182634-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4,5-(methylenedioxy)-2-aminoindan
• 英文别名: 4,5-Methylenedioxy-2-aminoindane；7,8-dihydro-6H-cyclopenta[g][1,3]benzodioxol-7-amine
• CAS: 182634-37-3
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: AHYFDWHTTFREHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-(methylenedioxy)-2-aminoindan 、 甲乙酐 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 N-(7,8-Dihydro-6H-1,3-dioxa-as-indacen-7-yl)-formamide
  参考文献：
  名称：

  Malmusi, Luca; Dukat, Malgorzata; Young, Richard, Medicinal Chemistry Research, 1996, vol. 6, # 6, p. 412 - 426

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-(亚甲二氧基)苯甲醛 在 palladium on activated charcoal 哌啶 、 盐酸 、 硫酸 、 氢气 、 phosphorus pentoxide 、 亚硝酸异戊酯 作用下， 以 吡啶 、 甲醇 、 乙醇 、 溶剂黄146 、 苯 为溶剂， 反应 11.0h， 生成 4,5-(methylenedioxy)-2-aminoindan
  参考文献：
  名称：

  Nonneurotoxic tetralin and indan analogs of 3,4-(methylenedioxy)amphetamine (MDA)

  摘要：

  Four cyclic analogues of the psychoactive phenethylamine derivative 3,4-(methylenedioxy)amphetamine were studied. These congeners, 5,6- and 4,5-(methylenedioxy)-2-aminoindan (3a and 4a, respectively), and 6,7- and 5,6-(methylenedioxy)-2-aminotetralin (3b and 4b, respectively) were tested for stimulus generalization in the two-lever drug-discrimination paradigm. Two groups of rats were trained to discriminate either LSD tartrate (0.08 mg/kg) from saline, or (+/-)-MDMA.HCl (1.75 mg/kg) from saline. In addition, a 2-aminoindan (5a) and 2-aminotetralin (5b) congener of the hallucinogenic amphetamine 1-(2,5-dimethoxy-4- methylphenyl)-2-aminopropane (DOM) were also evaluated. None of the methylenedioxy compounds substituted in LSD-trained rats, while both 3a and 3b fully substituted in MDMA-trained rats. Compounds 4a and 4b did not substitute in MDMA-trained rats. Compounds 5a and 5b did not substitute in MDMA-trained rats, although 5a substituted in LSD-trained rats, but with relatively low potency compared to its open-chain counterpart. In view of the now well-established serotonin neurotoxicity of 3,4-(methylenedioxy)amphetamine and its N-methyl homologue 1, 3a and 3b were evaluated and compared to 1 for similar toxic effects following a single acute dose of 40 mg/kg sc. Sacrifice at 1 week showed that neither 3a nor 3b depressed rat cortical or hippocampal 5-HT or 5-HIAA levels nor were the number of binding sites (Bmax) depressed for [3H]paroxetine. By contrast, and in agreement with other reports, 1 significantly depressed all three indices of neurotoxicity. These results indicate that 3a and 3b have acute behavioral pharmacology similar to 1 but that they lack similar serotonin neurotoxicity.

  DOI：

  10.1021/jm00164a037

文献信息

• Nonneurotoxic tetralin and indan analogs of 3,4-(methylenedioxy)amphetamine (MDA)
  作者：David E. Nichols、William K. Brewster、Michael P. Johnson、Robert Oberlender、Robert M. Riggs

  DOI：10.1021/jm00164a037

  日期：1990.2

  Four cyclic analogues of the psychoactive phenethylamine derivative 3,4-(methylenedioxy)amphetamine were studied. These congeners, 5,6- and 4,5-(methylenedioxy)-2-aminoindan (3a and 4a, respectively), and 6,7- and 5,6-(methylenedioxy)-2-aminotetralin (3b and 4b, respectively) were tested for stimulus generalization in the two-lever drug-discrimination paradigm. Two groups of rats were trained to discriminate either LSD tartrate (0.08 mg/kg) from saline, or (+/-)-MDMA.HCl (1.75 mg/kg) from saline. In addition, a 2-aminoindan (5a) and 2-aminotetralin (5b) congener of the hallucinogenic amphetamine 1-(2,5-dimethoxy-4- methylphenyl)-2-aminopropane (DOM) were also evaluated. None of the methylenedioxy compounds substituted in LSD-trained rats, while both 3a and 3b fully substituted in MDMA-trained rats. Compounds 4a and 4b did not substitute in MDMA-trained rats. Compounds 5a and 5b did not substitute in MDMA-trained rats, although 5a substituted in LSD-trained rats, but with relatively low potency compared to its open-chain counterpart. In view of the now well-established serotonin neurotoxicity of 3,4-(methylenedioxy)amphetamine and its N-methyl homologue 1, 3a and 3b were evaluated and compared to 1 for similar toxic effects following a single acute dose of 40 mg/kg sc. Sacrifice at 1 week showed that neither 3a nor 3b depressed rat cortical or hippocampal 5-HT or 5-HIAA levels nor were the number of binding sites (Bmax) depressed for [3H]paroxetine. By contrast, and in agreement with other reports, 1 significantly depressed all three indices of neurotoxicity. These results indicate that 3a and 3b have acute behavioral pharmacology similar to 1 but that they lack similar serotonin neurotoxicity.
• Malmusi, Luca; Dukat, Malgorzata; Young, Richard, Medicinal Chemistry Research, 1996, vol. 6, # 6, p. 412 - 426
  作者：Malmusi, Luca、Dukat, Malgorzata、Young, Richard、Teitler, Milt、Darmani, Nissar A.、Ahmad, Bashir、Smith, Carol、Glennon, Richard A.

  DOI：——

  日期：——