6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran | 99355-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran
• 英文别名: 75S5T5T7QX；1-(5-methoxy-2-methyl-2,3-dihydro-1-benzofuran-6-yl)propan-2-amine
• CAS: 99355-74-5
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: XBHKBTCXRYPZMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-dihydro-5-methoxy-2-methylbenzofuran 在 lithium aluminium tetrahydride 、 ammonium acetate 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Synthesis and evaluation of 2,3-dihydrobenzofuran analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats

  摘要：

  Two analogues, 6-(2-aminopropyl)-5-methoxy-2,3-dihydrobenzofuran and 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran, of the hallucinogenic agent 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) were synthesized and tested in the two-lever drug discrimination paradigm. In rats trained to discriminate saline from LSD tartrate (0.08 mg/kg), stimulus generalization occurred to both of the 2,3-dihydrobenzofuran analogues but at doses more than 10-fold higher than for DOM. A possible explanation for this dramatic attenuation of LSD-like activity could involve a highly directional electrophilic binding site on the receptor that cannot accept the orientation of the unshared electron pairs on the heterocyclic oxygen atom in the benzofurans.

  DOI：

  10.1021/jm00152a022

文献信息

• NICHOLS, D. E.;HOFFMAN, A. J.;OBERLENDER, R. A.;RIGGS, R. M., J. MED. CHEM., 1986, 29, N 2, 302-304
  作者：NICHOLS, D. E.、HOFFMAN, A. J.、OBERLENDER, R. A.、RIGGS, R. M.

  DOI：——

  日期：——
• Antiparkinsonian Action of Phenylisopropylamines
  申请人：Caron G. Marc

  公开号：US20070027208A1

  公开（公告）日：2007-02-01

  A method of treating a subject for Parkinson's disease comprises administering said subject a phenylisopropylamine in an amount effective to treat said Parkinson's disease. In some embodiments the method is used to treat at least a motor symptom of Parkinson's disease; in some embodiments the method is used to treat at least a non-motor symptom of Parkinson's disease.
• COMPOSITIONS COMPRISING A PSILOCYBIN DERIVATIVE AND A CANNABINOID
  申请人：CaaMTech, LLC

  公开号：US20190142851A1

  公开（公告）日：2019-05-16

  This disclosure pertains to new compositions and methods comprising a psilocybin derivative. In one embodiment, the compositions disclosed herein are used for a method of regulating a neurotransmitter receptor, e.g., a serotonin receptor. In one embodiment, the compositions disclosed herein comprise purified compounds, e.g., a purified psilocybin derivative, a purified cannabinoid, or purified terpene.
• COMPOSITIONS COMPRISING A SEROTONERGIC TRYPTAMINE COMPOUND
  申请人：CAAMTECH, INC.

  公开号：US20210346346A1

  公开（公告）日：2021-11-11

  Disclosed herein are compositions comprising a serotonergic tryptamine compound, combinations thereof, and methods of using them for treating and preventing a variety of human conditions. In one embodiment, disclosed herein are new compositions and methods which comprise a therapeutically effective amount of a first purified psilocybin derivative and a therapeutically effective amount of a second compound. The second compound is selected from the group consisting of a second purified psilocybin derivative, a purified terpene, a serotonergic drug, an adrenergic drug, a dopaminergic drug, a purified erinacine, and a purified hericenone.
• US8877802B2
  申请人：——

  公开号：US8877802B2

  公开（公告）日：2014-11-04