L-alpha-甲基多巴胺 | 14513-20-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: L-alpha-甲基多巴胺
• 英文名称: (+)-alpha-Methyldopamine
• 英文别名: (S)-(+)-1-(3,4-dihydroxyphenyl)-2-propanamine；(S)-3,4-dihydroxyamphetamine；S-DHA；L-dopa；(+)(L)-2-<3,4-Dihydroxy-phenyl>-1-methyl-aethylamin；L-alpha-Methyldopamine；4-[(2S)-2-aminopropyl]benzene-1,2-diol
• CAS: 14513-20-3
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: KSRGADMGIRTXAF-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-alpha-甲基多巴胺 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 (S)-(-)-1-(3,4-ethylenedioxyphenyl)propan-2-ylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  Ethylenedioxy homologs of N -methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine

  摘要：

  N-Methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA; 'Ecstasy'; 1) and its beta-keto analog methylone (MDMC; 2) are popular drugs of abuse. Little is known about their ring-expanded ethylenedioxy homologs. Here, we prepared N-methyl-(3,4-ethylenedioxyphenyl)-2-aminopropane (EDMA; 3), both of its optical isomers, and beta-keto EDMA (i.e., EDMC; 4) to examine their effects at transporters for serotonin (SERT), dopamine (DAT), and norepinephrine (NET). In general, ring-expansion of the methylenedioxy group led to a several-fold reduction in potency at all three transporters. With respect to EDMA (3), S(+)3 was 6-fold, 50-fold, and 8-fold more potent than its R(-) enantiomer at SERT, DAT, and NET, respectively. Overall, in the absence of a beta-carbonyl group, the ethylenedioxy (i.e., 1,4-dioxane) substituent seems better accommodated at SERT than at DAT and NET. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.035
• 作为产物：
  描述：

  (S)-1-(3,4-dibenzyloxyphenyl)-2-aminopropane 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 L-alpha-甲基多巴胺
  参考文献：
  名称：

  PRATESI; LAMANNA; GRANA, Farmaco, Edizione Scientifica, 1964, vol. 19, p. 529 - 536

  摘要：

  DOI：

文献信息

• US7608445B1
  申请人：——

  公开号：US7608445B1

  公开（公告）日：2009-10-27
• PRATESI; LAMANNA; GRANA, Farmaco, Edizione Scientifica, 1964, vol. 19, p. 529 - 536
  作者：PRATESI、LAMANNA、GRANA

  DOI：——

  日期：——
• Ethylenedioxy homologs of N -methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine
  作者：Fabio Del Bello、Farhana Sakloth、John S. Partilla、Michael H. Baumann、Richard A. Glennon

  DOI：10.1016/j.bmc.2015.07.035

  日期：2015.9

  N-Methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA; 'Ecstasy'; 1) and its beta-keto analog methylone (MDMC; 2) are popular drugs of abuse. Little is known about their ring-expanded ethylenedioxy homologs. Here, we prepared N-methyl-(3,4-ethylenedioxyphenyl)-2-aminopropane (EDMA; 3), both of its optical isomers, and beta-keto EDMA (i.e., EDMC; 4) to examine their effects at transporters for serotonin (SERT), dopamine (DAT), and norepinephrine (NET). In general, ring-expansion of the methylenedioxy group led to a several-fold reduction in potency at all three transporters. With respect to EDMA (3), S(+)3 was 6-fold, 50-fold, and 8-fold more potent than its R(-) enantiomer at SERT, DAT, and NET, respectively. Overall, in the absence of a beta-carbonyl group, the ethylenedioxy (i.e., 1,4-dioxane) substituent seems better accommodated at SERT than at DAT and NET. (C) 2015 Elsevier Ltd. All rights reserved.