9,10-didehydro-N,N-diethyl-6-cyanoergoline-8β-carboxamide | 35779-41-0

• 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: 9,10-didehydro-N,N-diethyl-6-cyanoergoline-8β-carboxamide
• 英文别名: N⁶-Cyano-norlysergic acid diethylamide；d-N⁶-Cyan-N⁶-demethyl-LSD；d-N⁶-Cyan-N⁶-demethyl-lysergsaeure-diethylamid；6-cyano-9,10-didehydro-ergoline-8-carboxylic acid diethylamide；8β-6-cyano-9,10-didehydro-N,N-diethylergoline-8-carboxamide；N-Cyanonor-LSD；(6aR,9R)-7-cyano-N,N-diethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• CAS: 35779-41-0
• 化学式: C₂₀H₂₂N₄O
• 分子量: 334.421
• InChiKey: PRJLFXBNAZPHEJ-RDTXWAMCSA-N

物化性质

• 沸点：
  625.1±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DCM、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9,10-didehydro-N,N-diethyl-6-cyanoergoline-8β-carboxamide 在 sodium acetate 、 溶剂黄146 、 锌 作用下， 反应 5.5h， 生成 麦角乙二胺
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  溴化氰 、 麦角乙二胺 以 四氯化碳 、 氯仿 为溶剂， 反应 6.0h， 以71%的产率得到9,10-didehydro-N,N-diethyl-6-cyanoergoline-8β-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

• Reagents for lysergic acid diethylamide immunoassay
  申请人：Roche Diagnostics Corporation

  公开号：US06063908A1

  公开（公告）日：2000-05-16

  The present invention provides hapten derivatives that are useful for the preparation of antigens, antibodies and reagents having superior performance characteristics for use in immunoassays for the detection of LSD and nor-LSD. In the present invention the LSD nucleus is derivatized out of the indole nitrogen to form an aminoalkyl derivative. Derivatives have also been synthesized out of the piperidine nitrogen of the LSD nucleus. The resulting haptens can then be further modified at these functionalized positions for linking to appropriate antigenic or labelling groups to provide reagents for LSD immunoassays having excellent sensitivity and selectivity for both LSD and nor-LSD.

  本发明提供了一种可用于制备抗原、抗体和试剂的半抗原衍生物，这些试剂在用于检测LSD和去甲-LSD的免疫分析中具有优良的性能特征。在本发明中，LSD核心通过吲哚氮原子衍生化形成氨基烷基衍生物。还从LSD核心的哌啶氮原子合成了衍生物。然后可以在这些功能化位置进一步修饰得到的半抗原，以便与适当的抗原或标记基团连接，为LSD免疫分析提供具有对LSD和去甲-LSD都具有极佳灵敏性和选择性的试剂。
• US6063908A
  申请人：——

  公开号：US6063908A

  公开（公告）日：2000-05-16
• US6476199B1
  申请人：——

  公开号：US6476199B1

  公开（公告）日：2002-11-05