4-benzyloxy-6-fluoro-N,N-dimethyltryptamine | 312314-32-2

• 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: 4-benzyloxy-6-fluoro-N,N-dimethyltryptamine
• 英文别名: [2-[4-(benzyloxy)-6-fluoroindol-3-yl]ethyl]dimethylamine；2-(4-benzyloxy-6-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine；2-(6-fluoro-4-phenylmethoxy-1H-indol-3-yl)-N,N-dimethylethanamine
• CAS: 312314-32-2
• 化学式: C₁₉H₂₁FN₂O
• 分子量: 312.387
• InChiKey: XYWMOFAJSCIDSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-6-fluoro-N,N-dimethyltryptamine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以36 mg的产率得到3-[2-(dimethylamino)ethyl]-6-fluoroindol-4-ol
  参考文献：
  名称：

  [EN] HETEROCYCLIC COMPOUNDS AND METHODS OF PREPARATION THEREOF
  [FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS PROCÉDÉS DE PRÉPARATION

  摘要：

  This disclosure relates to heterocyclic compounds of Formula (I), Formula (II), and Formula (III) as well as the preparation and use thereof. As contemplated herein, heterocyclic compounds of Formula (I), Formula (II), and Formula (III) may be used for the treatment of neuropsychiatric, and neurodegenerative, neuroinflammatory and pain disorders including depression, as well as tobacco, opiate, and cocaine addiction, alcoholism, post-traumatic stress disorder (PTSD), and neuropathic pain syndromes including cluster headaches and chemotherapy induced peripheral neuropathy. Formula (I), Formula (II), Formula (III)

  公开号：

  WO2022246554A1
• 作为产物：
  描述：

  3-氟苯酚 在 N-甲基吡咯烷酮 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 sodium methylate 、 铜 、 potassium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 、 xylene 为溶剂， 反应 62.5h， 生成 4-benzyloxy-6-fluoro-N,N-dimethyltryptamine
  参考文献：
  名称：

  Effect of Ring Fluorination on the Pharmacology of Hallucinogenic Tryptamines

  摘要：

  A series of fluorinated analogues of the hallucinogenic tryptamines N,N-diethyltryptamine (DET), 4-hydroxy-N,N-dimethyltryptamine (4-OH-DMT, psilocin), and 5-methoxy-DMT was synthesized to investigate possible explanations for the inactivity of 6-fluoro-DET as a hallucinogen and to determine the effects of fluorination on the molecular recognition and activation of these compounds at serotonin receptor subtypes. The target compounds were evaluated using in vivo behavioral assays for hallucinogen-like and 6-HT1A agonist activity and in vitro radioligand competition assays for their affinity at 5-HT2A, 5-HT2C, and 5-HT1A receptor sites. Functional activity at the 5-HT2A receptor was determined for all compounds. In addition, for some compounds functional activity was determined at the 5-HT1A receptor. Hallucinogen-like activity, evaluated in the two-lever drug discrimination paradigm using LSD-trained rats, was attenuated or abolished for all of the fluorinated analogues. One of the tryptamines, 4-fluoro-5-methoxy-DMT (6), displayed high 5-HT1A agonist activity, with potency greater than that of the 5-HT1A agonist 8-OH-DPAT. The ED50 Of 6 in the two-lever drug discrimination paradigm using rats trained to discriminate the 5-HT1A agonist LY293284 was 0.17 mu mol/kg, and the K-i at [H-3] 8-OH-DPAT-labeled 5-HT1A receptors was 0.23 nM. The results indicate that fluorination of hallucinogenic tryptamines generally has little effect on 5-HT2A/2C receptor affinity or intrinsic activity. Affinity at the 5-HT1A receptor was reduced, however, in all but one example, and all of the compounds tested were full agonists but with reduced functional potency at this serotonin receptor subtype. The one notable exception was 4-fluoro-5-methoxy-DMT (6), which had markedly enhanced 5-HT1A receptor affinity and functional potency. Although it is generally considered that hallucinogenic activity results from 5-HT2A receptor activation, the present results suggest a possible role for involvement of the 5-HT1A receptor with tryptamines.

  DOI：

  10.1021/jm000339w

文献信息

• [EN] COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：GALENEA CORP

  公开号：WO2011019738A1

  公开（公告）日：2011-02-17

  Indole compounds are disclosed. Also disclosed are methods for using the compounds to treat human and animal disease, pharmaceutical compositions of the compounds, and kits including the compounds.

  吲哚化合物已被披露。还披露了使用这些化合物治疗人类和动物疾病的方法，这些化合物的药物组合物，以及包含这些化合物的试剂盒。
• COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Elder Amy

  公开号：US20110144090A1

  公开（公告）日：2011-06-16

  Indole compounds are disclosed. Also disclosed are methods for using the compounds to treat human and animal disease, pharmaceutical compositions of the compounds, and kits including the compounds.

  揭示了吲哚化合物。还揭示了使用该化合物治疗人类和动物疾病的方法，该化合物的药物组成以及包括该化合物的试剂盒。
• Compounds and methods of use thereof
  申请人：Elder Amy

  公开号：US08912220B2

  公开（公告）日：2014-12-16

  Indole compounds are disclosed. Also disclosed are methods for using the compounds to treat human and animal disease, pharmaceutical compositions of the compounds, and kits including the compounds.

  本文披露了吲哚类化合物。此外，还披露了使用这些化合物治疗人类和动物疾病的方法，以及包含这些化合物的药物组合物和试剂盒。
• US8912220B2
  申请人：——

  公开号：US8912220B2

  公开（公告）日：2014-12-16