(8beta)-9,10-二去氢-N,N-二乙基-6-(2-丙烯基)-麦角灵-8-甲酰胺 | 65527-61-9

• 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
• 中文名称: (8beta)-9,10-二去氢-N,N-二乙基-6-(2-丙烯基)-麦角灵-8-甲酰胺
• 英文名称: 8β-6-allyl-6-norlysergic acid diethylamide
• 英文别名: 6-allyl-6-norlysergic acid diethylamide；N⁶-Allyl-norlysergic acid diethylamide；N-AllylnorLSD；6-allyl-9,10-didehydro-ergoline-8-carboxylic acid diethylamide；AL-Lad；(6aR,9R)-N,N-diethyl-7-prop-2-enyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• CAS: 65527-61-9
• 化学式: C₂₂H₂₇N₃O
• 分子量: 349.476
• InChiKey: JCQLEPDZFXGHHQ-OXQOHEQNSA-N

物化性质

• 熔点：
  >75°C (dec.)
• 沸点：
  558.2±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  39.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8beta)-9,10-二去氢-N,N-二乙基-6-(2-丙烯基)-麦角灵-8-甲酰胺 、 2-呋喃基(1H-咪唑-1-基)甲酮 以 乙腈 为溶剂， 以68 %的产率得到(6aR,9R)-N,N-diethyl-4-(furan-2-carbonyl)-7-prop-2-enyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
  参考文献：
  名称：

  [EN] PRODRUGS OF SUBSTITUTED ERGOLINES
  [FR] PROMÉDICAMENTS D'ERGOLINES SUBSTITUÉES

  摘要：

  The present invention relates generally to substituted ergoline compounds and compositions, more particularly new lysergamide derivatives and compositions, and applications of these. The invention furthermore relates to a new production process for 2-bromo lysergamide derivatives and intermediates of said production process.

  公开号：

  WO2024028495A1
• 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 10.5h， 生成 (8beta)-9,10-二去氢-N,N-二乙基-6-(2-丙烯基)-麦角灵-8-甲酰胺
  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

• Stachulski, Andrew V.; Nichols, David E.; Scheinmann, Feodor, Journal of Chemical Research - Part S, 1996, # 1, p. 30 - 31
  作者：Stachulski, Andrew V.、Nichols, David E.、Scheinmann, Feodor

  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.
• TRYPTAMINE COMPOSITIONS FOR ENHANCING NEURITE OUTGROWTH
  申请人：STAMETS Paul Edward

  公开号：US20210069170A1

  公开（公告）日：2021-03-11

  Described herein are neurotrophic and nootropic compositions and methods for treating subjects with such compositions. In one aspect the composition comprises one or more tryptamines or in pure form or extracts from psilocybin containing mushrooms, or combinations thereof optionally combined with one or more phenethylamines or amphetamines in pure form or extracts from a plant or mushroom, or combinations thereof, optionally one or more erinacines or hericenones in pure form, extracts from Hericium mushroom species (e.g., H. erinaceus, H. coralloides, H. ramosum ) or combinations thereof, optionally one or more cannabinoids in pure form or extracts from Cannabis sativa, Cannabis sativa, Cannabis indica , or Cannabis ruderalis , optionally, one or more adversive compounds, and optionally one or more pharmaceutically acceptable excipients.
• 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] TRYPTAMINE COMPOSITIONS FOR ENHANCING NEURITE OUTGROWTH<br/>[FR] COMPOSITIONS DE TRYPTAMINES DESTINÉES À AMÉLIORER L'EXCROISSANCE DES NEURITES
  申请人：STAMETS PAUL EDWARD

  公开号：WO2021101926A1

  公开（公告）日：2021-05-27

  Described herein are neurotrophic and nootropic compositions and methods for treating subjects with such compositions. In one aspect the composition comprises one or more tryptamines or in pure form or extracts from psilocybin containing mushrooms, or combinations thereof optionally combined with one or more phenethylamines or amphetamines in pure form or extracts from a plant or mushroom, or combinations thereof, optionally one or more erinacines or hericenones in pure form, extracts from Hericium mushroom species (e.g., H. erinaceus, H. coralloides, H. ramosum) or combinations thereof, optionally one or more cannabinoids in pure form or extracts from Cannabis sativa, Cannabis sativa, Cannabis indica, or Cannabis ruderalis, optionally, one or more adversive compounds, and optionally one or more pharmaceutically acceptable excipients.