4-(2-氨基丙基)-2-甲氧基苯酚 | 13062-61-8

• 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: 4-(2-氨基丙基)-2-甲氧基苯酚
• 英文名称: 4-hydroxy-3-methoxyamphetamine hydrochloride
• 英文别名: 4-(2-amino-propyl)-2-methoxy-phenol; hydrochloride；4-(2-aminopropyl)-2-methoxyphenol;hydrochloride
• CAS: 13062-61-8
• 化学式: C₁₀H₁₅NO₂*ClH
• 分子量: 217.696
• InChiKey: NHLXZOOGQNYXLV-UHFFFAOYSA-N

物化性质

• 熔点：
  251 °C (decomp)
• 溶解度：
  DMF：0.16mg/mL； DMSO：10mg/mL； PBS（pH 7.2）：5 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  14
• 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：
  55.5
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2922509090

反应信息

• 作为产物：
  描述：

  4-羟基-3-甲氧基苯丙酮 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 51.5h， 以36%的产率得到4-(2-氨基丙基)-2-甲氧基苯酚
  参考文献：
  名称：

  Comparative potencies of 3,4-methylenedioxymethamphetamine (MDMA) analogues as inhibitors of [³ H]noradrenaline and [³ H]5-HT transport in mammalian cell lines

  摘要：

  Background and purpose:Illegal ‘ecstasy’ tablets frequently contain 3,4‐methylenedioxymethamphetamine (MDMA)‐like compounds of unknown pharmacological activity. Since monoamine transporters are one of the primary targets of MDMA action in the brain, a number of MDMA analogues have been tested for their ability to inhibit [3H]noradrenaline uptake into rat PC12 cells expressing the noradrenaline transporter (NET) and [3H]5‐HT uptake into HEK293 cells stably transfected with the 5‐HT transporter (SERT).Experimental approach:Concentration–response curves for the following compounds at both NET and SERT were determined under saturating substrate conditions: 4‐hydroxy‐3‐methoxyamphetamine (HMA), 4‐hydroxy‐3‐methoxymethamphetamine (HMMA), 3,4‐methylenedioxy‐N‐hydroxyamphetamine (MDOH), 2,5‐dimethoxy‐4‐bromophenylethylamine (2CB), 3,4‐dimethoxymethamphetamine (DMMA), 3,4‐methylenedioxyphenyl‐2‐butanamine (BDB), 3,4‐methylenedioxyphenyl‐N‐methyl‐2‐butanamine (MBDB) and 2,3‐methylenedioxymethamphetamine (2,3‐MDMA).Key results:2,3‐MDMA was significantly less potent than MDMA at SERT, but equipotent with MDMA at NET. 2CB and BDB were both significantly less potent than MDMA at NET, but equipotent with MDMA at SERT. MBDB, DMMA, MDOH and the MDMA metabolites HMA and HMMA, were all significantly less potent than MDMA at both NET and SERT.Conclusions and implications:This study provides an important insight into the structural requirements of MDMA analogue affinity at both NET and SERT. It is anticipated that these results will facilitate understanding of the likely pharmacological actions of structural analogues of MDMA.British Journal of Pharmacology (2007) 152, 1121–1130; doi:10.1038/sj.bjp.0707473; published online 24 September 2007

  DOI：

  10.1038/sj.bjp.0707473

文献信息

• Demethyl analogs of psychoactive methoxyphenalkylamines: synthesis and serotonin receptor affinities
  作者：Richard A. Glennon、Stephen M. Liebowitz、Dianne Leming-Doot、John A. Rosecrans

  DOI：10.1021/jm00183a006

  日期：1980.9

  5-dimethoxyphenalkylamines increases their affinity for the serotonin receptors of the isolated rat fundus preparation. In several instances, demethylation of methoxyphenalkylamines results in compounds which produce an antagonism which is not of a competitive nature. With respect to 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM), demethylation of the 2-methoxy group alters affinity in a manner which parallels

  几种2，5-二甲氧基苯烷基胺的单O-去甲基化增加了它们对离体大鼠眼底制剂中血清素受体的亲和力。在几种情况下，甲氧基苯烷基胺的去甲基化导致化合物产生拮抗作用，该拮抗作用不是竞争性的。关于1-（2,5-二甲氧基-4-甲基苯基）-2-氨基丙烷（DOM），2-甲氧基的去甲基化以与5-甲氧基-N，N的脱甲基化所观察到的平行的方式改变亲和力。 -二甲基色胺。使用判别性刺激范式，对大鼠的行为研究显示，DOM的2-羟基类似物而非5-羟基类似物产生的作用（感受暗示）类似于5-甲氧基-N，N-二甲基色胺。