(2-碘苯基)(1-((1-甲基哌啶-2-基)甲基)-1H-吲哚-3-基)甲酮 | 444912-75-8

• 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
• 中文名称: (2-碘苯基)(1-((1-甲基哌啶-2-基)甲基)-1H-吲哚-3-基)甲酮
• 英文名称: AM2233
• 英文别名: (2-iodophenyl)[1-[(1-methyl-2-piperidinyl)methyl]-1H-indol-3-yl]methanone；(2-iodophenyl)-[1-[(1-methylpiperidin-2-yl)methyl]indol-3-yl]methanone
• CAS: 444912-75-8
• 化学式: C₂₂H₂₃IN₂O
• 分子量: 458.342
• InChiKey: KSLCYQTUSSEGPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-碘苯基)(1-((1-甲基哌啶-2-基)甲基)-1H-吲哚-3-基)甲酮 在 四(三苯基膦)钯 、 六正丁基二锡 、 盐酸 、 sodium iodide 、 chloroamine-T 作用下， 以 甲苯 、 乙醇 为溶剂， 反应 18.08h， 生成 [131I]2-iodophenyl-[1-(1-methylpiperidin-2-ylmethyl)-1H-indol-3-yl]methanone
  参考文献：
  名称：

  Potent Cannabinergic Indole Analogues as Radioiodinatable Brain Imaging Agents for the CB1 Cannabinoid Receptor

  摘要：

  A series of novel aminoalkylindoles was synthesized in an effort to develop compounds that are potent agonists at the CB1 cannabinoid receptor and that are also easily labeled with radioisotopes of iodine for biochemical and imaging studies. 2-iodophenyl-[1-(l-methylpiperidin2-ylmethyl)]-1H-indol-3-yllmethanone (8, AM2233) had a very high affinity for the rat CB1 receptor, with most of the affinity residing with the (R)-enantiomer. Radioiodinated 8, (R)-8, and (S)-8 were prepared by radioiododestannylation of the tributyltin analogues in high yields, radiochemical purities, and specific radioactivities. In a mouse hippocampal membrane preparation with [I-131](R)-8 as radioligand, racemic 8 exhibited a K-i value of 0.2 nM compared with 1.6 nM for WIN55212-2. In autoradiographic experiments with mouse brain sections, the distribution of radioiodinated 8 was consistent with that of brain CB1 receptors. Again, very little specific binding was seen with the (S)-enantiomer [I-131](S)-8 and none occurred with the (R)-enantiomer [I-131] (R)-8 in sections from CB1 receptor knockout mice. Radioiodinated 8 thus appears to be a suitable radioligand for studies of CB1 cannabinoid receptors.

  DOI：

  10.1021/jm050135l
• 作为产物：
  描述：

  N-(N-甲基哌啶基)甲基吲哚 、 邻碘苯甲酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到(2-碘苯基)(1-((1-甲基哌啶-2-基)甲基)-1H-吲哚-3-基)甲酮
  参考文献：
  名称：

  Potent Cannabinergic Indole Analogues as Radioiodinatable Brain Imaging Agents for the CB1 Cannabinoid Receptor

  摘要：

  A series of novel aminoalkylindoles was synthesized in an effort to develop compounds that are potent agonists at the CB1 cannabinoid receptor and that are also easily labeled with radioisotopes of iodine for biochemical and imaging studies. 2-iodophenyl-[1-(l-methylpiperidin2-ylmethyl)]-1H-indol-3-yllmethanone (8, AM2233) had a very high affinity for the rat CB1 receptor, with most of the affinity residing with the (R)-enantiomer. Radioiodinated 8, (R)-8, and (S)-8 were prepared by radioiododestannylation of the tributyltin analogues in high yields, radiochemical purities, and specific radioactivities. In a mouse hippocampal membrane preparation with [I-131](R)-8 as radioligand, racemic 8 exhibited a K-i value of 0.2 nM compared with 1.6 nM for WIN55212-2. In autoradiographic experiments with mouse brain sections, the distribution of radioiodinated 8 was consistent with that of brain CB1 receptors. Again, very little specific binding was seen with the (S)-enantiomer [I-131](S)-8 and none occurred with the (R)-enantiomer [I-131] (R)-8 in sections from CB1 receptor knockout mice. Radioiodinated 8 thus appears to be a suitable radioligand for studies of CB1 cannabinoid receptors.

  DOI：

  10.1021/jm050135l

文献信息

• Formulations and methods for treating acute cannabinoid overdose
  申请人：Anebulo Pharmaceuticals, Inc.

  公开号：US11141404B1

  公开（公告）日：2021-10-12

  Described herein are uses of the CB1 inhibitors (e.g., antagonists, neutral antagonists, inverse agonists) and various methods of using and administering a CB1 inhibitor to a patient, especially patients showing symptoms of drug overdose or suspected of a drug overdose. Further described herein are uses wherein the CB1 inhibitor is ANEB-001. Further described herein are treatments with a CB1 inhibitor for THC or synthetic cannabinoid overdose.

  本文描述了CB1抑制剂（如拮抗剂、中性拮抗剂、逆激动剂）的用途，以及向患者，特别是出现药物过量症状或疑似药物过量的患者使用和施用CB1抑制剂的各种方法。本文进一步描述了CB1抑制剂为ANEB-001的用途。本文还描述了使用 CB1 抑制剂治疗四氢大麻酚或合成大麻素过量的方法。
• COMPOSITIONS AND METHODS FOR TREATING ACUTE CANNABINOID OVERDOSE WITH A CANNABINOID RECEPTOR ANTAGONIST
  申请人：Opiant Pharmaceuticals, Inc.

  公开号：EP3890724A1

  公开（公告）日：2021-10-13
• FORMULATIONS AND METHODS FOR TREATING ACUTE CANNABINOID OVERDOSE
  申请人：Anebulo Pharmaceuticals, Inc.

  公开号：US20220151990A1

  公开（公告）日：2022-05-19

  Described herein are uses of the CB1 inhibitors (e.g., antagonists, neutral antagonists, inverse agonists) and various methods of using and administering a CB1 inhibitor to a patient, especially patients showing symptoms of drug overdose or suspected of a drug overdose. Further described herein are uses wherein the CB1 inhibitor is ANEB-001. Further described herein are treatments with a CB1 inhibitor for THC or synthetic cannabinoid overdose.
• [EN] COMPOSITIONS AND METHODS FOR TREATING ACUTE CANNABINOID OVERDOSE WITH A CANNABINOID RECEPTOR ANTAGONIST<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE TRAITEMENT D'UN SURDOSAGE AIGU AU CANNABINOÏDE AVEC UN ANTAGONISTE DU RÉCEPTEUR CANNABINOÏDE
  申请人：OPIANT PHARMACEUTICALS INC

  公开号：WO2020118048A1

  公开（公告）日：2020-06-11

  Disclosed herein are formulations and methods for reversing cannabinoid overdose or one or more symptoms thereof, comprising parenterally administering a CB1 antagonist in an amount sufficient to reverse the cannabinoid overdose or symptom(s).
• [EN] COMPOSITIONS AND METHODS FOR TREATING ACUTE CANNABINOID OVERDOSE WITH A CANNABINOID RECEPTOR ANTAGONIST<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT DU SURDOSAGE AIGU AUX CANNABINOÏDES AVEC UN ANTAGONISTE DES RÉCEPTEURS CANNABINOÏDES
  申请人：OPIANT PHARMACEUTICALS INC

  公开号：WO2020257333A1

  公开（公告）日：2020-12-24

  Provided are formulations and methods for treating, reversing, or reducing acute cannabinoid overdose, cannabinoid hyperemesis syndrome, or one or more symptoms thereof, comprising parenterally administering a CB 1 antagonist in an amount sufficient to reverse the acute cannabinoid overdose, cannabinoid hyperemesis syndrome, or symptom(s) thereof.