1-<2,5-dimethoxy-4-(2-butyl)phenyl>-2-nitropropene | 89556-68-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-<2,5-dimethoxy-4-(2-butyl)phenyl>-2-nitropropene
• 英文别名: 1-(Butan-2-yl)-2,5-dimethoxy-4-(2-nitroprop-1-en-1-yl)benzene；1-butan-2-yl-2,5-dimethoxy-4-(2-nitroprop-1-enyl)benzene
• CAS: 89556-68-3
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: GBOOFQUHWKYFHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<2,5-dimethoxy-4-(2-butyl)phenyl>-2-nitropropene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1-(4-仲-丁基-2,5-二甲氧基苯基)-2-丙胺
  参考文献：
  名称：

  Substituent branching in phenethylamine-type hallucinogens: a comparison of 1-[2,5-dimethoxy-4-(2-butyl)phenyl]-2-aminopropane and 1-[2,5-dimethoxy-4-(2-methylpropyl)phenyl]-2-aminopropane

  摘要：

  Two novel hallucinogen analogues related to 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM, STP) were synthesized and evaluated in the two-lever drug discrimination paradigm by using 0.08 mg/kg of LSD as the training drug stimulus. The two compounds differ from each other only with respect to the point of branching in the 4-alkyl group. However, pharmacological evaluation revealed a clear difference in difference in potency and degree of LSD generalization for the two isomers. Branching adjacent to the ring, as in the 4-(2-butyl) analogue, may provide steric interference to the formation of the drug-receptor complex, while branching one methylene unit removed from the ring, as in the 4-(2-methylpropyl) analogue, poses less of a steric problem for the drug-receptor interaction. This is consistent with the idea that formation of a charge-transfer complex between the hallucinogen molecule and the receptor may be one of the features of this drug-receptor interaction.

  DOI：

  10.1021/jm00372a015
• 作为产物：
  描述：

  2,5-二甲氧基苯乙酮 在 palladium on activated charcoal ammonium acetate 、 氢气 、 四氯化钛 、 对甲苯磺酸 、 magnesium 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.5h， 生成 1-<2,5-dimethoxy-4-(2-butyl)phenyl>-2-nitropropene
  参考文献：
  名称：

  Substituent branching in phenethylamine-type hallucinogens: a comparison of 1-[2,5-dimethoxy-4-(2-butyl)phenyl]-2-aminopropane and 1-[2,5-dimethoxy-4-(2-methylpropyl)phenyl]-2-aminopropane

  摘要：

  Two novel hallucinogen analogues related to 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM, STP) were synthesized and evaluated in the two-lever drug discrimination paradigm by using 0.08 mg/kg of LSD as the training drug stimulus. The two compounds differ from each other only with respect to the point of branching in the 4-alkyl group. However, pharmacological evaluation revealed a clear difference in difference in potency and degree of LSD generalization for the two isomers. Branching adjacent to the ring, as in the 4-(2-butyl) analogue, may provide steric interference to the formation of the drug-receptor complex, while branching one methylene unit removed from the ring, as in the 4-(2-methylpropyl) analogue, poses less of a steric problem for the drug-receptor interaction. This is consistent with the idea that formation of a charge-transfer complex between the hallucinogen molecule and the receptor may be one of the features of this drug-receptor interaction.

  DOI：

  10.1021/jm00372a015

文献信息

• Substituent branching in phenethylamine-type hallucinogens: a comparison of 1-[2,5-dimethoxy-4-(2-butyl)phenyl]-2-aminopropane and 1-[2,5-dimethoxy-4-(2-methylpropyl)phenyl]-2-aminopropane
  作者：Robert A. Oberlender、Paresh J. Kothari、David E. Nichols、Joseph E. Zabik

  DOI：10.1021/jm00372a015

  日期：1984.6

  Two novel hallucinogen analogues related to 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM, STP) were synthesized and evaluated in the two-lever drug discrimination paradigm by using 0.08 mg/kg of LSD as the training drug stimulus. The two compounds differ from each other only with respect to the point of branching in the 4-alkyl group. However, pharmacological evaluation revealed a clear difference in difference in potency and degree of LSD generalization for the two isomers. Branching adjacent to the ring, as in the 4-(2-butyl) analogue, may provide steric interference to the formation of the drug-receptor complex, while branching one methylene unit removed from the ring, as in the 4-(2-methylpropyl) analogue, poses less of a steric problem for the drug-receptor interaction. This is consistent with the idea that formation of a charge-transfer complex between the hallucinogen molecule and the receptor may be one of the features of this drug-receptor interaction.