N,N-dimethyltryptamine fumarate | 68677-26-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-dimethyltryptamine fumarate
• 英文别名: 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine hemi-fumarate；DMT fumarate；Dimethyltryptamine fumarate；(E)-but-2-enedioic acid;2-(1H-indol-3-yl)-N,N-dimethylethanamine
• CAS: 68677-26-9
• 化学式: C₄H₄O₄*2C₁₂H₁₆N₂
• 分子量: 492.618
• InChiKey: OHMVTPSXVQQKPA-WLHGVMLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-吲哚乙酸 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.91h， 生成 N,N-dimethyltryptamine fumarate
  参考文献：
  名称：

  [EN] INJECTABLE FORMULATION
  [FR] FORMULATION INJECTABLE

  摘要：

  本文提供了制药配方、制造方法及其用途。该制药配方包括一种可选取代的二甲基色胺盐、一个与盐分离的缓冲剂和水。该配方的pH值约为3.5至6.5，渗透压约为250至350 mOsm/Kg。这种配方可选用于注射，具有稳定性和临床可接受性，并有潜在用途于治疗精神或神经疾病。

  公开号：

  WO2022043227A1

文献信息

• [EN] THERAPEUTIC COMPOSITIONS COMPRISING DEUTERATED OR PARTIALLY DEUTERATED N,N-DIMETHYLTRYPTAMINE COMPOUNDS<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES COMPRENANT DES COMPOSÉS DE N,N-DIMÉTHYLTRYPTAMINE DEUTÉRÉS OU PARTIELLEMENT DEUTÉRÉS
  申请人：SMALL PHARMA LTD

  公开号：WO2020245133A1

  公开（公告）日：2020-12-10

  The present invention relates to compositions comprising N,N-dimethyltryptamine, deuterated N,N-dimethyltryptamine and/or partially deuterated N,N-dimethyltryptamine. In particular, the present invention relates to compositions comprising a combination of N,N-dimethyltryptamine and 2% or more by weight of one or more deuterated N,N- dimethyltryptamine compound selected from α,α-dideutero-N,N-dimethyltryptamine and α,α,β,β-tetradeutero-N,N-dimethyltryptamine. Additional and alternative compositions of the present invention comprise a combination of N,N-dimethyltryptamine and 2% or more by weight of one or more partially deuterated N,N-dimethyltryptamine compound selected from α,β,β-trideutero-N,N-dimethyltryptamine, α,β-dideutero-N,N- dimethyltryptamine, and α-deutero-N,N-dimethyltryptamine. Methods of synthesising compositions of the present invention, and methods of use of presently described compositions in treating psychiatric or psychocognitive disorders, such as major depressive disorder, are also provided.

  本发明涉及包含N,N-二甲基色胺、氘代N,N-二甲基色胺和/或部分氘代N,N-二甲基色胺的组合物。具体来说，本发明涉及包含N,N-二甲基色胺和占总重量2%或更多的一种或多种氘代N,N-二甲基色胺化合物的组合物，所述氘代N,N-二甲基色胺化合物选自α,α-二氘代N,N-二甲基色胺和α,α,β,β-四氘代N,N-二甲基色胺。本发明的其他和替代组合物包括N,N-二甲基色胺和占总重量2%或更多的一种或多种部分氘代N,N-二甲基色胺化合物的组合物，所述部分氘代N,N-二甲基色胺化合物选自α,β,β-三氘代N,N-二甲基色胺、α,β-二氘代N,N-二甲基色胺和α-氘代N,N-二甲基色胺。还提供了本发明组合物的合成方法，以及描述的组合物在治疗精神疾病或心理认知障碍，如重度抑郁症中的使用方法。
• Discovery and <i>In Vitro</i> Characterization of SPL028: Deuterated <i>N</i>,<i>N</i>-Dimethyltryptamine
  作者：Marie Layzell、Peter Rands、Meghan Good、Zelah Joel、Rick Cousins、Tiffanie Benway、Ellen James、Carol Routledge

  DOI：10.1021/acsmedchemlett.3c00143

  日期：2023.9.14

  However, when administered via intravenous infusion, its effects are short-lived due to rapid clearance. Here we describe the synthesis of deuterated analogues of DMT with the aim of prolonging the half-life and decreasing the clearance rate while maintaining similar pharmacological effects. The molecule with the greatest degree of deuteration at the α-carbon (N,N-D2-dimethyltryptamine, D2-DMT) demonstrated

  迷幻剂N , N-二甲基色胺 (DMT) 正在临床开发中，用于治疗重度抑郁症。然而，当通过静脉输注给药时，由于快速清除，其作用是短暂的。在这里，我们描述了 DMT 氘代类似物的合成，目的是延长半衰期并降低清除率，同时保持相似的药理作用。与 DMT 相比，α-碳上氘化程度最高的分子（ N , N -D 2 -二甲基色胺，D 2 -DMT）在肝细胞线粒体部分中表现出最长的半衰期和内在清除率。 D 2 -DMT 的体外受体结合谱与 DMT 相当，对 5-HT 1A 、5-HT 2A和 5-HT 2C受体具有最高亲和力。因此，D 2 -DMT 是考虑进一步评估的首选候选者。
• Effects of <i>N</i>,<i>N</i>-Dimethyltryptamine on Rat Behaviors Relevant to Anxiety and Depression
  作者：Lindsay P. Cameron、Charlie J. Benson、Lee E. Dunlap、David E. Olson

  DOI：10.1021/acschemneuro.8b00134

  日期：2018.7.18

  Depression and anxiety disorders are debilitating diseases resulting in substantial economic costs to society. Traditional antidepressants often take weeks to months to positively affect mood and are ineffective for about 30% of the population. Alternatives, such as ketamine, a dissociative anesthetic capable of producing hallucinations, and the psychoactive tisane ayahuasca, have shown great promise due to their fast-acting nature and effectiveness in treatment-resistant populations. Here, we investigate the effects of N,N-dimethyltryptamine (DMT), the principle hallucinogenic component of ayahuasca, in rodent behavioral assays relevant to anxiety and depression using adult, male, Sprague-Dawley rats. We find that while DMT elicits initial anxiogenic responses in several of these paradigms, its long-lasting effects tend to reduce anxiety by facilitating the extinction of cued fear memory. Furthermore, DMT reduces immobility in the forced swim test, which is a characteristic behavioral response induced by many antidepressants. Our results demonstrate that DMT produces antidepressant and anxiolytic behavioral effects in rodents, warranting further investigation of ayahuasca and classical psychedelics as treatments for depression and post-traumatic stress disorder.
• [EN] N,N-DIMETHYLTRYPTAMINE (DMT) CRYSTALLINE PRODUCTS AND METHODS OF MAKING THE SAME<br/>[FR] PRODUITS CRISTALLINS N,N-DIMÉTHYLTRYPTAMINE (DMT) ET LEURS PROCÉDÉS DE FABRICATION
  申请人：[en]PSILERA INC.

  公开号：WO2023076135A1

  公开（公告）日：2023-05-04

  An effective and efficient process for obtaining a crystalline products comprised of salts ofN,N-Dimethyltryptamine (DMT) freebase is provided. The crystalline products may, for example, be DMT fumarate, DMT tartrate, DMT succinate, or DMT maleate.
• [EN] TRYPTAMINE COMPOSITIONS AND METHODS<br/>[FR] COMPOSITIONS DE TRYPTAMINE ET PROCÉDÉS
  申请人：[en]CYBIN IRL LIMITED

  公开号：WO2023135237A1

  公开（公告）日：2023-07-20

  There are disclosed pharmaceutically acceptable salts of tryptamine compounds, the use of such salt forms in the treatment of diseases associated with a serotonin 5-HT2receptor, pharmaceutical compositions such as those adapted for inhalation administration containing the salt forms, methods of delivering the pharmaceutically acceptable salt forms (e.g., via inhalation), and methods of treating diseases or disorders associated with a serotonin 5-HT2receptor, such as central nervous system (CNS) disorders or psychological disorders, with the salt forms. (Formula (I))