(6aR,9R)-7-butyl-N,N-diethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide | 96930-87-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: (6aR,9R)-7-butyl-N,N-diethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• 英文别名: BU-Lad
• CAS: 96930-87-9
• 化学式: C₂₃H₃₁N₃O
• 分子量: 365.519
• InChiKey: VTVHSIXDKKKTMT-DYESRHJHSA-N

物化性质

• 沸点：
  567.7±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  39.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  麦角乙二胺 在 potassium carbonate 、 锌 作用下， 以 四氯化碳 、 氯仿 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.0h， 生成 (6aR,9R)-7-butyl-N,N-diethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
  参考文献：
  名称：

  Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives

  摘要：

  A convenient method for the synthesis of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives was developed. A series of these compounds was synthesized and tested for substitution in the two-lever drug discrimination assay, in rats trained to discriminate injections of d-LSD tartrate (185.5 nmol/kg, ip) from saline. A dose-response curve for each of the compounds in the series was generated. Structure-activity relationships were developed, based on comparison of the estimated ED50 values from these curves. Of the compounds that substituted for LSD, the N(6)-ethyl and -allyl were approximately 2-3 times more potent than LSD itself. The N(6)-propyl was equipotent to LSD, while the isopropyl derivative was half as active. The n-butyl compound was 1 order of magnitude less potent than LSD, suggesting a similarity to the SAR of certain serotonin and dopamine agonists. By contrast, no generalization occurred to norlysergic acid N,N-diethylamide and the N(6)-2-phenethyl derivative.

  DOI：

  10.1021/jm00147a022

文献信息

• 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 NEUROLOGICAL CONDITIONS<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT DE PATHOLOGIES NEUROLOGIQUES
  申请人：[en]WESANA HEALTH INC.

  公开号：WO2022115796A1

  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 neurological conditions (e.g., traumatic brain injury or TBI), or symptoms thereof (e.g., anxiety or depression), 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., TBI), or symptoms thereof (e.g., anxiety or depression).
• [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).
• [EN] NOVEL ERGOLINES AND METHODS OF TREATING MOOD DISORDERS<br/>[FR] NOUVELLES ERGOLINES ET PROCÉDÉS DE TRAITEMENT DE TROUBLES DE L'HUMEUR
  申请人：[en]GILGAMESH PHARMACEUTICALS, INC.

  公开号：WO2022226408A1

  公开（公告）日：2022-10-27

  The present disclosure provides ergoline compounds and their use in treating mood disorders. Pharmaceutical compositions and methods of making various ergoline compounds are provided.