6-去甲麦角酸二乙基酰胺 | 35779-43-2

• 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: 6-去甲麦角酸二乙基酰胺
• 英文名称: nor-LSD
• 英文别名: N-Demethyllysergic acid diethylamide；(6aR,9R)-N,N-diethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
• CAS: 35779-43-2
• 化学式: C₁₉H₂₃N₃O
• 分子量: 309.411
• InChiKey: SUXLVXOMPKZBOV-CXAGYDPISA-N

物化性质

• 溶解度：
  酒精：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  48.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  T
• 危险类别码：
  R23/24/25
• 危险品运输编号：
  UN 2811 6
• 海关编码：
  2933990090
• 安全说明：
  S36/37/39,S45

反应信息

• 作为反应物：
  描述：

  6-去甲麦角酸二乙基酰胺 、 碘甲烷 反应 1.0h， 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：

  麦角乙二胺 在 溴化氰 、 溶剂黄146 、 锌 作用下， 以 水 为溶剂， 以67%的产率得到6-去甲麦角酸二乙基酰胺
  参考文献：
  名称：

  Synthetic LSD metabolite for preparing haptens used in an LSD metabolite immunoassay

  摘要：

  已成功开发了一种合成OH-LSD及其类似物的通用方法。这种方法方便高效，可以制备一系列在不同位置（C-8、N-6或N-1）附有连接子的OH-LSD类似物。

  公开号：

  US20060223998A1

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。
• Special ergolines are highly selective, potent antagonists of the chemokine receptor CXCR3: Discovery, characterization and preliminary SAR of a promising lead
  作者：Gebhard Thoma、Rolf Baenteli、Ian Lewis、Trixie Wagner、Lukas Oberer、Wolfgang Blum、Fraser Glickman、Markus B. Streiff、Hans-Guenter Zerwes

  DOI：10.1016/j.bmcl.2009.09.002

  日期：2009.11

  The special ergoline 1 is a highly potent, selective antagonist of the chemokine receptor CXCR3. The surprising selectivity of this LSD-related compound can be explained by different electronic and steric properties of the ergoline core structure caused by the urea portion of the molecule. Discovery, biopharmaceutical properties and first derivatives of this promising lead compound are discussed.

  特殊麦角灵1是趋化因子受体CXCR3的高效，选择性拮抗剂。该LSD相关化合物的惊人的选择性可以通过由分子的脲部分引起的麦角灵核心结构的不同电子和空间特性来解释。讨论了这种有前途的先导化合物的发现，生物制药性能和一阶衍生物。
• Ergoline Derivatives
  申请人：Baenteli Rolf

  公开号：US20090018127A1

  公开（公告）日：2009-01-15

  Disclosed are ergoline derivatives, Formula (I), wherein either each of R 1 and R 2 , independently, is H; optionally R 10 and/or R 11 -substituted-phenyl or -phenyl-C 1-4 alkyl; optionally R 10 and/or R 11 -substituted-heteroaryl or -heteroaryl-C 1-4 alkyl; optionally R 10 and/or R 11 -substituted heteroaryl N-oxide; optionally R 10 -substituted C 1 -C 8 alkyl; optionally R 10 -substituted C 2 -C 8 alkenyl, optionally R 10 -substituted C 2 -C 8 alkynyl; optionally R 10 -substituted C 3 -C 8 cycloalkyl, or optionally R 10 -substituted C 4 -C 8 cycloalkenyl; or R 1 and R 2 form together with the nitrogen atom to which they are attached an optionally R 10 -substituted 3-8 membered ring containing in addition to the nitrogen atom up to 2 heteroatoms selected independently from N, O and S; R 3 is H; OR 1 ; CH 2 R 1 R 2 ; (CH 2 ) 1-2 NR 1 R 2 ; CH 2 —CH 2 —OR 1 ; CH 2 —CO—NR 1 R 2 ; or CO—CH 2 R 1 R 2 ; R 4 is F; Cl; Br; I; OR 1 ; NR 1 R 2 or has one of the significances given for R 1 ; and R 5 has one of the significances given for R 1 , in free form or in salt form for preventing or treating disorders or diseases mediated by interactions between chemokine receptors and their ligands.

  本发明涉及一种聚乙酰胺衍生物，化学式（I），其中R1和R2中的每个独立地为H；可选地为R10和/或R11取代的苯基或苯基-C1-4烷基；可选地为R10和/或R11取代的杂环芳基或杂环芳基-C1-4烷基；可选地为R10和/或R11取代的杂环芳基-N-氧化物；可选地为R10取代的C1-C8烷基；可选地为R10取代的C2-C8烯基，可选地为R10取代的C2-C8炔基；可选地为R10取代的C3-C8环烷基，或可选地为R10取代的C4-C8环烯基；或者R1和R2与它们连接的氮原子一起形成一个可选地取代的3-8成员环，除氮原子外，还含有最多2个独立选择的杂原子，从N、O和S中选择；R3为H、OR1、CH2R1R2、（CH2）1-2NR1R2、CH2—CH2—OR1、CH2—CO—NR1R2或CO—CH2R1R2；R4为F、Cl、Br、I、OR1、NR1R2或具有R1给出的其中一个意义；R5具有R1给出的其中一个意义，在自由形式或盐形式中，用于预防或治疗由趋化因子受体和它们的配体之间的相互作用介导的疾病或疾病。
• Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives
  作者：Andrew J. Hoffman、David E. Nichols

  DOI：10.1021/jm00147a022

  日期：1985.9

  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.
• ERGOLINE DERIVATIVES AND THEIR USE AS CHEMOKINE RECEPTOR LIGANDS
  申请人：Novartis AG

  公开号：EP1893611A1

  公开（公告）日：2008-03-05