N,N-dimethylisotryptamine | 87482-09-5

• 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: N,N-dimethylisotryptamine
• 英文别名: 2-(1H-indol-1-yl)-N,N-dimethylethan-1-amine；1-(N,N-dimethylamino)ethylindole；(2-Indol-1-yl-ethyl)-dimethyl-amine；2-indol-1-yl-N,N-dimethylethanamine
• CAS: 87482-09-5
• 化学式: C₁₂H₁₆N₂
• 分子量: 188.272
• InChiKey: PSHKCPACSIZILK-UHFFFAOYSA-N

物化性质

• 沸点：
  300.1±25.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dimethylisotryptamine 以 溶剂黄146 为溶剂， 反应 0.21h， 生成 5-{1-[2-(N,N-dimethylamino)ethyl]indol-3-yl}-10,11-dihydro-5H-dibenzo-[a,d]cycloheptene
  参考文献：
  名称：

  钢丝上的二氧化碳：稳定化，室温脱羧和钠诱导的羧酸盐迁移

  摘要：

  通过吲哚的连续化学选择性双烷基化反应合成了具有空间屏蔽作用的3-取代的两性离子N，N-二甲基异胰二铵羧​​酸盐。在室温下，羧酸盐会在二甲基亚砜（DMSO）或二甲基甲酰胺（DMF）中进行定量且异常容易的脱羧。溶剂分子破坏几乎等距的氢键会引发杂化CC裂解。脱羧速率随CO 2的增加而降低分压，证明了碳负离子中间体的质子化和再羧化的竞争力。相应的含有亚甲硅烷基和亚锡亚烷基部分的螺环化合物显示出高的热稳定性。向钠盐中添加过量的甲基锂会触发反应序列，该反应序列包括去质子化，羧酸盐转移以及另一等价的甲基锂对重排的羧酸盐的亲核捕获。对双羟甲基双羟乙酸酯进行水解后可得到乙酰基产物。氘代实验尚未阐明钠抗衡离子的作用和重排的机理。

  DOI：

  10.1002/chem.201202298
• 作为产物：
  描述：

  吲哚 、 2-氯-N,N-二甲基乙胺 在 sodium hydride 作用下， 生成 N,N-dimethylisotryptamine
  参考文献：
  名称：

  Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines

  摘要：

  A novel series of N,N-dimethylisotryptamine (isoDMT) derivatives, i.e., derivatives of 1-[2-(dimethylamino)ethyl]indole, was prepared and found to be isosteric with their corresponding N,N-dimethyltryptamine (DMT) counterparts with respect to serotonin receptor (rat fundus) affinity. Whereas the isoDMT derivatives possessed a greater affinity than did their corresponding DMT derivatives, they were relatively ineffective in displacing [3H]-5-HT binding from rat brain (cortex) homogenates. In a drug discrimination paradigm, using rats as subjects, 6-OMe-isoDMT produced effects similar to those of 5-OMe-DMT. Attempts to antagonize the discriminative stimulus effects of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) using two of the isoDMT derivatives proved unsuccessful.

  DOI：

  10.1021/jm00367a008

文献信息

• 1-(AMINOALKYL)-3-SULFONYLINDOLE AND-INDAZOLE DERIVATIVES AS 5-HYDROXYTRYPTAMINE-6 LIGANDS
  申请人：Wyeth

  公开号：US20030232828A1

  公开（公告）日：2003-12-18

  The present invention provides compounds of formula I and the use thereof for the treatment of central nervous system disorders related to or affected by the 5-HT6 receptor. 1

  本发明提供了化合物I的公式以及其用于治疗与5-HT6受体相关或受其影响的中枢神经系统疾病的用途。
• Rare-earth metal complexes supported by indolyl-based NCN-pincer ligand and their efficient catalysis for isoprene polymerization
  作者：Cheng-Hao Chu、Xiang-Rui Wang、Jiang-Sheng Huang、Ze-Ming Huang、Qing-Hai Li、Fen-Hua Wang

  DOI：10.1016/j.molstruc.2023.135498

  日期：2023.8

  Rare-earth metal dialkyl complexes [1-CH2N(CH3)2–3-CH2CH2N(CH3)2C8H4N]RE(CH2SiMe3)2 (RE = 1-Y, 2-Er, 3-Yb and 4-Lu) were synthesized by the well-designed indolyl-based proligand 1-CH2N(CH3)2–3-CH2CH2N(CH3)2C8H4NH with rare-earth metal trialkyl complexes (RE(CH2SiMe3)2(THF)2) underwent direct alkane elimination. Single-crystal X-ray analyses and the NMR spectroscopy revealed these dialkyl complexes were analogous

  稀土金属二烷基配合物[1-CH 2 N(CH 3 ) 2 –3-CH 2 CH 2 N(CH 3 ) 2 C 8 H 4 N]RE(CH 2 SiMe 3 ) 2 (RE = 1-Y , 2-Er, 3-Yb 和 4-Lu) 由精心设计的基于吲哚基的前体 1-CH 2 N(CH 3 ) 2 –3-CH 2 CH 2 N(CH 3 ) 2 C 8 H合成4 NH与稀土金属三烷基络合物(RE(CH 2 SiMe3 ) 2 (THF) 2 ) 进行直接烷烃消除。单晶 X 射线分析和核磁共振光谱表明，这些二烷基配合物通过2-sp 2吲哚的 C H 活化，具有类似的单核 NCN 钳形结构。使用这些络合物，在被烷基铝和硼酸盐活化后，引发了具有高转化率和高立体选择性的异戊二烯聚合反应（2000 当量异戊二烯的转化率为 98%，1,4-顺式聚合物的转化率高达 91.5%）。
• Rare-Earth Metal Complexes Supported by 1,3-Functionalized Indolyl-Based Ligands for Efficient Hydrosilylation of Alkenes
  作者：Shan Zhu、Wenxiang Xu、Dongjing Hong、Weikang Wu、Fuxiang Chai、Xiancui Zhu、Shuangliu Zhou、Shaowu Wang

  DOI：10.1021/acs.inorgchem.2c03488

  日期：2023.1.9

  rare-earth metal chemistry showing different reactivities and different bondings with the central metals. The reactions of HL1 with RE(CH2SiMe3)3(THF)2 provided two types of rare-earth metal complexes: the pincer type mononuclear complexes κ3-(L1)RE(CH2SiMe3)2 [L1 = 1-(2-C4H7O)CH2-3-(2-tBuC6H5N═CH)C8H4N, RE = Lu(1), Yb(2)], and the dinuclear rare-earth metal alkyl (per alkyl/per metal) complexes having

  两种不同的 1,3-功能化吲哚基前体 1-(2-C 4 H 7 O)CH 2 -3-(2- t BuC 6 H 5 N =CH)C 8 H 5 N ( HL 1 ) 和 1 -Me 2 NCH 2 CH 2 -3-(2- i PrC 6 H 5 N =CH)C 8 H 5 N ( HL 2 ) 被设计、高收率制备，并成功应用于稀土金属化学，表现出不同反应性和与中心金属的不同键合。的反应HL 1与RE(CH 2 SiMe 3 ) 3 (THF) 2提供了两种类型的稀土金属配合物：钳型单核配合物κ 3 -( L 1 )RE(CH 2 SiMe 3 ) 2 [ L 1 = 1 -(2-C 4 H 7 O)CH 2 -3-(2- t BuC 6 H 5 N= CH)C 8 H 4 N, RE = Lu( 1 ), Yb( 2)], 以及具有新配位模式配体的双核稀土金属烷基(每烷基/每金属)配合物(η
• N-substituted indoles and other heterocycles for treating brain disorders
  申请人：The Regents of the University of California

  公开号：US11254640B2

  公开（公告）日：2022-02-22

  The present invention provides N-substituted indoles and other heterocycles and methods of using the compounds for treating brain disorders.

  本发明提供了 N-取代吲哚和其他杂环化合物以及使用这些化合物治疗脑部疾病的方法。
• [DE] INDOLOCARBAZOL-IMIDE UND DEREN VERWENDUNG<br/>[EN] INDOLOCARBAZOLE IMIDES AND THEIR USE<br/>[FR] INDOLOCARBAZOL-IMIDES ET LEUR UTILISATION
  申请人：GÖDECKE AKTIENGESELLSCHAFT

  公开号：WO1993024491A1

  公开（公告）日：1993-12-09

  (DE) Gegenstand der Erfindung ist die Verwendung von Indolocarbazol-Imiden der allgemeinen Formel (I) zur Herstellung von Arzneimitteln zur Behandlung und/oder Prävention von Krebs, Viruserkrankungen (z.B. HIV-Infektionen), Herz- und Gefäßerkrankungen (wie z.B. Bluthochdruck, Thrombose, Herzrhythmusstörungen, Atherosklerose), bronchopulmonalen Erkrankungen, degenerativen Erkrankungen des Zentralnervensystems (z.B. Alzheimer), Entzündungskrankheiten (z.B. Rheuma, Arthritis), Krankheiten des Immunsystems (z.B. Allergien), sowie Psoriasis oder zur Verwendung als Immunsuppressivum sowie neue Verbindungen der Formel (I).(EN) The object of the invention is the use of indolocarbazole imides of general formula (I) for the production of medicaments for the treatment and/or prevention of cancer, viral diseases (e.g. HIV infections), cardiac and circulatory disorders (e.g. hypertension, thrombosis, cardiac rhythm irregularities, atherosclerosis), broncho-pulmonary diseases, degenerative diseases of the central nervous system (e.g. Alzheimer's disease), inflammatory conditions (e.g. rheumatism, arthritis) diseases of the immune system (e.g. allergies) and psoriasis, or for use as immunosuppressors, and novel compounds of formula (I).(FR) L'invention a pour objet l'utilisation d'indolocarbazol-imides ayant la formule générale (I) pour la fabrication de médicaments destinés au traitement et/ou à la prévention du cancer, de maladies virales (par exemple, infections HIV), maladies cardiovasculaires (telles que, par exemple, hypertension artérielle, thrombose, troubles du rythme cardiaque, athérosclérose), maladies bronchopulmonaires, maladies de dégénérescence du système nerveux central (par exemple, maladie d'Alzheimer), affections inflammatoires (par exemple, rhumatisme, arthrite), maladies du système immunitaire (par exemple, allergies), et psoriasis, ou pour l'utilisation comme immunodépresseur, ainsi que les nouveaux composés de formule (I).

  (DE) Der Ziele der Erfindung ist die Verwendung von Indolocarbazol-Imiden der allgemeinen Formel (I) zur Herstellung von Arzneimitteln zur Behandlung und/oder Prävention von Krebs, Viruserkrankungen (wie z.B. HIV-Infektionen), Herz- und Gefäßerkrankungen (wie z.B. Bluthochdruck, Thrombose, Herzrhythmusstörungen, Atherosklerose), bronchopulmonalen Erkrankungen, degenerativen Erkrankungen des Zentralnervensystems (wie z.B. Alzheimer), Entzündungskrankheiten (wie z.B. Rheuma, Arthritis), Krankheiten des Immunsystems (wie z.B. Allergien), sowie Psoriasis oder zur Verwendung als Immunsuppressivum sowie neue Verbindungen der Formel (I). (EN) The object of the invention is the use of indolocarbazole imides of general formula (I) for the production of medicaments for the treatment and/or prevention of cancer, viral diseases (e.g. HIV infections), cardiac and circulatory disorders (e.g. hypertension, thrombosis, cardiac rhythm irregularities, atherosclerosis), broncho-pulmonary diseases, degenerative diseases of the central nervous system (e.g. Alzheimer's disease), inflammatory conditions (e.g. rheumatism, arthritis) diseases of the immune system (e.g. allergies) and psoriasis, or for use as immunosuppressors, and novel compounds of formula (I). (FR) L'invention a pour objet l'utilisation d'indolocarbazol-imides ayant la formule générale (I) pour la fabrication de médicaments destinés au traitement et/ou à la précération du cancer, de maladies virales (par exemple, infections HIV), maladies cardiovasculaires (telles que, par exemple, hypertension artérielle, thromvoie, troubles du rythme cardiaque, athérosclérophe), maladies bronchopulmonaires, maladies de dégénérescence du système nerveux central (par exemple, maladie d'Alzheimer), affections inflammatoires (par exemple, rhumatisme, arthrite), maladies du système immunitaire (par exemple, allergies), et psoriasis, ou pour l'utilisation comme immunodépresseur, ainsi que les nouveaux composés de formule (I).