1-(5-methoxyindol-3-yl)-2-aminobutane | 4765-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(5-methoxyindol-3-yl)-2-aminobutane
• 英文别名: 1-(5-methoxy-indol-3-ylmethyl)-propylamine；3-<2-Amino-butyl>-5-methoxy-indol；3-(2-Amino-butyl)-5-methoxy-indol；5-Methoxy-alpha-ethyltryptamine；1-(5-methoxy-1H-indol-3-yl)butan-2-amine
• CAS: 4765-10-0
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: JHTPCKWBFLMJMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  393.3±27.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：5mg/mL； DMSO：11mg/mL； DMSO:PBS(pH7.2)(1:1)：0.5mg/ml；乙醇：10mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-methoxyindol-3-yl)-2-aminobutane 、 乙醛酸 以 甲醇 、 水 为溶剂， 生成 3-ethyl-6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylic acid
  参考文献：
  名称：

  Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  A structure-activity relationship study was conducted on a series of tetrahydro-beta-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNF alpha production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity. (c) 2007 Elsevier Ltd. All rialuts reserved.

  DOI：

  10.1016/j.bmcl.2007.05.070
• 作为产物：
  描述：

  5-甲氧基吲哚-3-甲醛 在 哌啶 、 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 1-(5-methoxyindol-3-yl)-2-aminobutane
  参考文献：
  名称：

  Synthesis and structure–activity relationship of novel conformationally restricted analogues of serotonin as 5-HT₆ receptor ligands

  摘要：

  5-Hydroxytryptamine 6 receptors (5-HT6R) are being perceived as the possible target for treatment of cognitive disorders as well as obesity. The present article deals with the design, synthesis, in vitro binding and structure-activity relationship of a novel series of tetracyclic tryptamines with the rigidized N-arylsulphonyl, N-arylcarbonyl and N-benzyl substituents as 5-HT6 receptor ligands. The chiral sulphonyl derivatives 15a and 17a showed high affinity at 5-HT6R with the K-i of 23.4 and 20.5 nM, respectively. The lead compound from the series 15a has acceptable ADME properties, adequate brain penetration and is active in animal models of cognition like Novel Object Recognition Task (NORT) and water maze.

  DOI：

  10.3109/14756366.2011.595713

文献信息

• Nickel boride/hydrazine hydrate reduction of aromatic and aliphatic nitro compounds. Synthesis of 4-(benzyloxy)indole and .alpha.-alkyltryptamines
  作者：David H. Lloyd、David E. Nichols

  DOI：10.1021/jo00372a037

  日期：1986.10
• LLOYD D. H.; NICHOLS D. E., J. ORG. CHEM., 51,(1986) N 22, 4294-4295
  作者：LLOYD D. H.、 NICHOLS D. E.

  DOI：——

  日期：——
• 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.
• [EN] COMPOSITIONS AND METHODS FOR TREATING MIGRAINE<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT DE LA MIGRAINE
  申请人：[en]WESANA HEALTH INC.

  公开号：WO2022115798A2

  公开（公告）日：2022-06-02

  As described below, the present disclosure features compositions containing a cannabidiol (CBD) and/or psilocybin, optionally in combination with a mushroom blend. The present disclosure also features methods for treating or preventing migraine, or symptoms thereof, with a cannabidiol and/or psilocybin, optionally in combination with a mushroom blend. The present disclosure also features compositions and methods of using psilocybin in combination with a neurotransmitter activity modulator for the treatment of neurological conditions (e.g., migraine), or symptoms thereof (e.g., anxiety or depression).