25CN-NBOH | 1391489-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 25CN-NBOH
• 英文别名: N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine；2-([2-(4-cyano-2,5-dimethoxyphenyl)ethylamino]methyl)phenol；Nboh-2C-CN；4-[2-[(2-hydroxyphenyl)methylamino]ethyl]-2,5-dimethoxybenzonitrile
• CAS: 1391489-32-9
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: VWEDZTZAXHMZIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  74.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-hydroxydibenzo[b,d]furan-4-carbaldehyde 、 25CN-NBOH 在 甲醇 、 sodium tetrahydroborate 作用下， 生成
  参考文献：
  名称：

  大体积 N-二苯并呋喃基甲基取代对迷幻苯乙胺 5-HT2 受体亲和力和功效的影响

  摘要：

  在苯乙胺和色胺的胺氮原子上引入芳甲基取代基通常会导致它们对 5-HT 2血清素受体的亲和力和功能活性显着增加。为了探讨这种效应对更大的N取代基的敏感性，通过在碱性氮上添加不同的二苯并[ b , d ]呋喃甲基 (DBFM) 部分，制备了十种已充分表征的迷幻苯乙胺 2C-B 的衍生物。 DBFM 基团通过 1-、-2-或 3-位连接到氨基上，降低了对 5-HT 2A/2C受体的亲和力和激动剂活性。通过 4 位的取代通常有利于对所有三种 5-HT 2受体亚型的亲和力，其中化合物5对 5-HT 2A和 5-HT 2C受体的亲和力分别高出 10 倍和 40 倍，但选择性低于四倍三种受体亚型之间。然而，所有这些都是相对较弱的部分5-HT 2A R 激动剂，大部分在低微摩尔范围内，但在钙动员测定中确定为5-HT 2C亚型的完全或接近完全激动剂。分子对接模拟表明，二苯并呋喃部分比 5-HT 2C受体更深入地进入

  DOI：

  10.1021/acschemneuro.3c00639
• 作为产物：
  描述：

  3-(2,5-二甲氧苯基)丙酸 在 N-溴代丁二酰亚胺(NBS) 、 叠氮磷酸二苯酯 、 甲烷磺酸(2-二环己基膦基-2',4',6'-三-异丙基-1,1'-联苯基)(2'-氨基-1,1'-联苯-2-基)钯(II) 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 反应 28.0h， 生成 25CN-NBOH
  参考文献：
  名称：

  [EN] PHENALKYLAMINES AND METHODS OF MAKING AND USING THE SAME
  [FR] PHÉNALKYLAMINES ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION

  摘要：

  本公开提供了苯基烷胺化合物及其在治疗医学疾病（如精神科疾病和障碍）中的应用。提供了制备各种苯基烷胺化合物的制药组合物和方法。

  公开号：

  WO2022192781A1

文献信息

• 5-HT2A AGONISTS FOR USE IN TREATMENT OF DEPRESSION
  申请人：Lophora ApS

  公开号：US20210137908A1

  公开（公告）日：2021-05-13

  The present invention relates to agonists of the 5-HT 2A serotonin receptors and their medical uses. In one aspect the invention relates to 5-HT 2A agonists of formula (I). In second aspect, the invention relates to selective 5-HT 2A agonists of formula (II). In another aspect, the invention relates to mixed 5-HT 2A /5-HT 2C agonists of formula (III). In yet another aspect, the invention relates to 5-HT 2A agonists for use in the treatment of a depressive disorder, more particular a 5-HT 2A agonist for the use in the treatment of treatment-resistant depression.

  本发明涉及5-HT2A 5-羟色胺受体的激动剂及其医疗用途。在一个方面，本发明涉及式(I)的5-HT2A激动剂。在第二个方面，本发明涉及式(II)的选择性5-HT2A激动剂。在另一个方面，本发明涉及式(III)的混合5-HT2A/5-HT2C激动剂。在另一个方面，本发明涉及用于治疗抑郁症的5-HT2A激动剂，更具体地说是用于治疗难治性抑郁症的5-HT2A激动剂。
• 5-HT2A agonists for use in treatment of depression
  申请人：Lophora ApS

  公开号：US11246860B2

  公开（公告）日：2022-02-15

  The present invention relates to agonists of the 5-HT2A serotonin receptors and their medical uses. In one aspect the invention relates to 5-HT2A agonists of formula (I). In second aspect, the invention relates to selective 5-HT2A agonists of formula (II). In another aspect, the invention relates to mixed 5-HT2A/5-HT2C agonists of formula (III). In yet another aspect, the invention relates to 5-HT2A agonists for use in the treatment of a depressive disorder, more particular a 5-HT2A agonist for the use in the treatment of treatment-resistant depression.

  本发明涉及 5-HT2A 血清素受体的激动剂及其医疗用途。一方面，本发明涉及式（I）的 5-HT2A 激动剂。第二方面，本发明涉及式（II）的选择性 5-HT2A 激动剂。另一方面，本发明涉及式（III）的 5-HT2A/5-HT2C 混合激动剂。再一方面，本发明涉及用于治疗抑郁障碍的5-HT2A激动剂，尤其是用于治疗耐药抑郁症的5-HT2A激动剂。
• Synthesis and Structure–Activity Relationships of <i>N</i>-Benzyl Phenethylamines as 5-HT_2A/2C Agonists
  作者：Martin Hansen、Karina Phonekeo、James S. Paine、Sebastian Leth-Petersen、Mikael Begtrup、Hans Bräuner-Osborne、Jesper L. Kristensen

  DOI：10.1021/cn400216u

  日期：2014.3.19

  N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5-dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule to determine the effects on receptor binding affinity and functional activity at 5-HT2A and 5-HT2c receptors. The compounds generally had high affinity for the 5-HT2A receptor with 8b having the highest affinity at 0.29 nM but with several other compounds also exhibiting subnanomolar binding affinities. The functional activity of the compounds was distributed over a wider range with lb being the most potent at 0.074 nM. Most of the compounds exhibited low to moderate selectivity (1- to 40-fold) for the 5-HT2A receptor in the binding assays, although one compound 6b showed an impressive 100-fold selectivity for the 5-HT2A receptor. In the functional assay, selectivity was generally higher with lb being more than 400-fold selective for the 5-HT2A receptor.
• 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.