1-<2-(benzyloxy)-5-methoxyphenyl>-2-aminopropane | 61552-27-0

• 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-(benzyloxy)-5-methoxyphenyl>-2-aminopropane
• 英文别名: 1-(5-Methoxy-2-phenylmethoxyphenyl)propan-2-amine
• CAS: 61552-27-0
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: AIRBRNLRZNUKNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1-<2-(benzyloxy)-5-methoxyphenyl>-2-aminopropane 在 氢溴酸 、 溴 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 1-<2-(benzyloxy)-4-bromo-5-methoxyphenyl>-2-aminopropane hydrobromide
  参考文献：
  名称：

  5-HT1 and 5-HT2 binding characteristics of 1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane analogs

  摘要：

  1-(2,5-Dimethoxy-4-bromophenyl)-2-aminopropane (DOB; 1a) is a purported serotonin (5-HT) agonist that binds selectively to central 5-HT2 binding sites. Systematic removal of any or all of the aromatic substituents had relatively little effect on 5-HT1 binding but reduced 5-HT2 binding by approximately 2 or more orders of magnitude. Demethylation of the 2-methoxy group of 1a, or introduction of an N-n-propyl group, doubled 5-HT1-site affinity but decreased 5-HT2-site affinity by 3- and 30-fold, respectively. In tests of stimulus generalization, using rats trained to discriminate DOM from saline, the 2-demethyl and N-propyl derivatives were found to produce stimulus effects similar to those of DOB. In addition, the S-(+) isomer of the iodo analogue of 1a was found to possess one-third the affinity of its R-(-) enantiomer at 5-HT2 sites and also resulted in DOM-stimulus generalization. Of the DOB analogues examined, DOB (1a) possesses optimal selectivity for 5-HT2 binding.

  DOI：

  10.1021/jm00152a005
• 作为产物：
  描述：

  2-苄氧基-5-甲氧基-苯甲醛 在 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 20.0h， 生成 1-<2-(benzyloxy)-5-methoxyphenyl>-2-aminopropane
  参考文献：
  名称：

  精神活性甲氧基苯烷基胺的去甲基类似物：合成和血清素受体亲和力。

  摘要：

  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。

  DOI：

  10.1021/jm00183a006

文献信息

• In vitro O-demethylation of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane
  作者：Jonathan S. Zweig、Neal Castagnoli

  DOI：10.1021/jm00213a020

  日期：1977.3

  O-demethylation of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (1, DOM, STP). Employing a sensitive and highly selective stable isotope dilution assay, we observed that rabbit liver homogenates biotransform the amine 1 to its 2-O-demethyl, 5-O-demethyl, and bis (O-demethyl) metabolite metabolites. Both monophenolic metabolites are enriched in their S enantiomers. The bis(O-demethyl) metabolite has structural

  甲氧基化的1-苯基-2-氨基丙烷之间的代谢与拟精神活性之间的可能关系导致我们对1-（2,5-二甲氧基-4-甲基苯基）-2-氨基丙烷（1， DOM，STP）。采用灵敏且高度选择性的稳定同位素稀释测定法，我们观察到兔肝脏匀浆将胺1生物转化为其2-O-脱甲基，5-O-脱甲基和双（O-脱甲基）代谢产物。两种单酚代谢物均富含其S对映体。双（O-去甲基）代谢产物具有与交感剂“ 6-羟基多巴胺”相似的结构，化学和电化学性质。根据胺1的拟精神特性，讨论了代谢O-去甲基化的可能意义。
• GLENNON R. A.; LIEBOWITZ S. M.; LEMING-DOOT D.; ROSECRANS J. A., J. MED. CHEM., 1980, 23, NO 9, 990-994
  作者：GLENNON R. A.、 LIEBOWITZ S. M.、 LEMING-DOOT D.、 ROSECRANS J. A.

  DOI：——

  日期：——
• GLENNON, R. A.;MCKENNEY, J. D.;LYON, R. A.;TITELER, M., J. MED. CHEM., 1986, 29, N 2, 194-199
  作者：GLENNON, R. A.、MCKENNEY, J. D.、LYON, R. A.、TITELER, M.

  DOI：——

  日期：——
• 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。
• 5-HT1 and 5-HT2 binding characteristics of 1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane analogs
  作者：Richard A. Glennon、J. D. McKenney、Robert A. Lyon、Milt Titeler

  DOI：10.1021/jm00152a005

  日期：1986.2

  1-(2,5-Dimethoxy-4-bromophenyl)-2-aminopropane (DOB; 1a) is a purported serotonin (5-HT) agonist that binds selectively to central 5-HT2 binding sites. Systematic removal of any or all of the aromatic substituents had relatively little effect on 5-HT1 binding but reduced 5-HT2 binding by approximately 2 or more orders of magnitude. Demethylation of the 2-methoxy group of 1a, or introduction of an N-n-propyl group, doubled 5-HT1-site affinity but decreased 5-HT2-site affinity by 3- and 30-fold, respectively. In tests of stimulus generalization, using rats trained to discriminate DOM from saline, the 2-demethyl and N-propyl derivatives were found to produce stimulus effects similar to those of DOB. In addition, the S-(+) isomer of the iodo analogue of 1a was found to possess one-third the affinity of its R-(-) enantiomer at 5-HT2 sites and also resulted in DOM-stimulus generalization. Of the DOB analogues examined, DOB (1a) possesses optimal selectivity for 5-HT2 binding.