(+/-)-1-(4-methylthiophenyl)-2-aminopropane hydrochloride | 94784-92-6

• 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-(4-methylthiophenyl)-2-aminopropane hydrochloride
• 英文别名: (RS)-2-amino-1-(4-methylsulfanylphenyl)propane hydrochloride；4-Methylthioamphetamine hydrochloride；2-amino-1-(4-methylthiophenyl)propane hydrochloride；alpha-Methyl-4-(methylthio)-benzeneethanamine,monohydrochloride；1-(4-methylsulfanylphenyl)propan-2-amine;hydrochloride
• CAS: 94784-92-6
• 化学式: C₁₀H₁₅NS*ClH
• 分子量: 217.763
• InChiKey: DGCZWGSFSFNXNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.41
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(4-methylthiophenyl)-2-aminopropane hydrochloride 在 三氟过氧乙酸 、 盐酸 作用下， 以 乙醚 、 异丙醇 为溶剂， 反应 5.0h， 以67%的产率得到1-(4-methylsulfonylphenyl)-2-aminopropane hydrochloride
  参考文献：
  名称：

  S-OXIDATION PRODUCTS OF ALKYLTHIOAMPHETAMINES

  摘要：

  The preparation of the sulfoxides and the sulfones of two centrally active alkylthioamphetamine salts, (+/-)-1-(4-methylthiophenyl)-2-aminopropane hydrochloride (2) (MTA . HCl) and (+/-)-1-(2,5-dimethoxy-4-ethylthiophenyl)-2-aminopropane hydrochloride (7) (ALEPH-2 . HCl), is described.

  DOI：

  10.1081/scc-120006041
• 作为产物：
  描述：

  4-甲硫基安非他明 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 生成 (+/-)-1-(4-methylthiophenyl)-2-aminopropane hydrochloride
  参考文献：
  名称：

  Synthesis and serotonin transporter activity of sulphur-substituted α-alkyl phenethylamines as a new class of anticancer agents

  摘要：

  The discovery that some serotonin reuptake transporter (SERT) ligands have the potential to act as pro-apoptotic agents in the treatment of cancer adds greatly to their diverse pharmacological application. 4-Methylthioamphetamine (MTA) is a selective ligand for SERT over other monoamine transporters. In this study, a novel library of structurally diverse 4-MTA analogues were synthesised with or without N-alkyl and/or C-alpha methyl or ethyl groups so that their potential SERT-dependent antiproliferative activity could be assessed.Many of the compounds displayed SERT-binding activity as well as cytotoxic activity. While there was no direct correlation between these two effects, a number of derivatives displayed anti-tumour effects in lymphoma, leukaemia and breast cancer cell lines, showing further potential to be developed as possible chemotherapeutic agents. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.07.027

文献信息

• Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted α-alkylthioamphetamines
  作者：Suzanne M. Cloonan、John J. Keating、Desmond Corrigan、John E. O’Brien、Pierce V. Kavanagh、D. Clive Williams、Mary J. Meegan

  DOI：10.1016/j.bmc.2010.04.022

  日期：2010.6.1

  drugs often contain byproducts of uncontrolled, illegal clandestine synthetic processes. We report the isolation and structural identification of a number of novel pyridines, dihydropyridone and N,N-di(1-aryl-2-propyl) amines as route-specific byproducts associated with clandestine synthesis of 4-MTA and related amphetamines. We report the in vitro cytotoxicity of 4-MTA, its synthesis byproducts together

  4-甲硫基苯丙胺（4-MTA）被认为是一种3,4-亚甲二氧基甲基苯丙胺（MDMA）滥用药物。这种苯丙胺类药物通常含有不受控制的非法秘密合成过程的副产物。我们报告了许多新型吡啶，二氢吡啶酮和N，N的分离和结构鉴定-二（1-芳基-2-丙基）胺是与4-MTA和相关苯丙胺的秘密合成有关的途径特定的副产物。我们报告了4-MTA的体外细胞毒性，其合成副产物与一些结构相关的硫取代的α-烷基苯乙胺在过度表达人单胺转运蛋白的细胞系以及主要神经元细胞系模型和多巴胺能神经母细胞瘤细胞系中。在药理定义的浓度范围内，发现4-MTA以及许多其他与结构相关的苯丙胺衍生物和合成杂质对这些细胞具有细胞毒性，这表明4-MTA在体外是细胞毒性剂，因此可能具有神经毒性剂的潜力。体内。
• Human and rat monoamine oxidase-A are differentially inhibited by (S)-4-alkylthioamphetamine derivatives: Insights from molecular modeling studies
  作者：Angélica Fierro、Mauricio Osorio-Olivares、Bruce K. Cassels、Dale E. Edmondson、Silvia Sepúlveda-Boza、Miguel Reyes-Parada

  DOI：10.1016/j.bmc.2007.05.021

  日期：2007.8

  Four enantiomerically pure (S)-4-alkylthioamphetamine derivatives were evaluated as monoamine oxidase (MAO) inhibitors using the human and rat isoforms of the enzyme. Molecular dockings were performed in order to gain insights regarding the binding mode of these inhibitors. All compounds were potent and selective MAO-A inhibitors although different rank orders of potencies were observed against the enzymes from different species. This behavior can be rationalized on the basis of different binding modes to each enzyme, as determined in silico. These findings further support the concept that MAO inhibitory activity of novel compounds, determined with enzymes from diverse mammalian species, should be considered with caution if human MAO is the final target to be addressed. (c) 2007 Elsevier Ltd. All rights reserved.