N-(adamantan-1-yl)-1-pentyl-1H-indole-3-carboxamide | 1345973-50-3

• 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-(adamantan-1-yl)-1-pentyl-1H-indole-3-carboxamide
• 英文别名: APICA；SDB-001；Apica；N-(1-adamantyl)-1-pentylindole-3-carboxamide
• CAS: 1345973-50-3
• 化学式: C₂₄H₃₂N₂O
• 分子量: 364.531
• InChiKey: MDJYHWLDDJBTMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,2,2-三氟-1-(1-戊基-1H-吲哚-3-基)乙烷-1-酮 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 N-(adamantan-1-yl)-1-pentyl-1H-indole-3-carboxamide
  参考文献：
  名称：

  新一代氮杂吲哚-金刚烷基衍生的合成大麻素

  摘要：

  目的这项工作报告了新发现的一系列新的氮杂吲哚-金刚烷基衍生的合成大麻素（SC）的合成以及药理和分析数据。 方法使用有效且发散的合成方法合成每个SC，并通过电子电离质谱（EIMS）进行评估。使用荧光成像板读数器（FLIPR）分析进行每种化合物的仿拟活性。 结果所描述的EIMS方法和气相色谱保留时间能够有效区分每种类似物，而与双环核无关。在这些SC结构中，双环系统首次显示出对膜电位的荧光测定法对大麻模拟活性的影响。类似物的范围从在CB 1和CB 2上均适度有效（例如，AP4AIC EC 50  = 160 nM和EC 50  = 64 nM）到对任一大麻素受体（AP4AICA，AP5AICA和APIC）均无效。 结论进一步研究围绕这些双环核心的受体选择性可能证明对未来的治疗应用有用。

  DOI：

  10.1007/s11419-019-00466-1

文献信息

• IMMUNOASSAY FOR SYNTHETIC CANNABINOIDS OF THE ADAMANTYL INDAZOLE/INDOLE-3-CARBOXAMIDE FAMILY
  申请人：Randox Laboratories Limited

  公开号：US20150346227A1

  公开（公告）日：2015-12-03

  An immunoassay method for detecting and determining adamantane substituted indazole and indole synthetic cannabinoids is described. Also described are components for use in implementing the method, namely, antibodies, detection agents, solid state devices and kits as well as immunogens used to raise the antibodies.

  本文描述了一种用于检测和确定取代了金刚烷的吲唑和吲哚合成大麻素的免疫测定方法。还描述了用于实施该方法的组分，即抗体、检测试剂、固态设备和试剂盒，以及用于制备抗体的免疫原。
• IMMUNOASSAY FOR SYNTHETIC CANNABINOIDS OF THE 3-ADAMANTANYL INDAZOLE/INDOLE-3-CARBOXAMIDE FAMILY
  申请人：Randox Laboratories Ltd.

  公开号：EP2950103A1

  公开（公告）日：2015-12-02

  An immunoassay method for detecting and determining adamantane substituted indazole and indole synthetic cannabinoids is described. Also described are components for use in implementing the method, namely, antibodies, detection agents, solid state devices and kits as well as immunogens used to raise the antibodies.

  描述了一种用于检测和确定金刚烷取代的吲唑和吲哚合成大麻素的免疫测定方法。还描述了用于实施该方法的组件，即抗体、检测剂、固态装置和试剂盒以及用于提高抗体的免疫原。
• Immunoassay for synthetic cannabinoids of the adamantyl indazole/indole-3-carboxamide family
  申请人：Randox Laboratories Limited

  公开号：US10591497B2

  公开（公告）日：2020-03-17

  An immunoassay method for detecting and determining adamantane substituted indazole and indole synthetic cannabinoids is described. Also described are components for use in implementing the method, namely, antibodies, detection agents, solid state devices and kits as well as immunogens used to raise the antibodies.

  描述了一种用于检测和确定金刚烷取代的吲唑和吲哚合成大麻素的免疫测定方法。还描述了用于实施该方法的组件，即抗体、检测剂、固态装置和试剂盒以及用于提高抗体的免疫原。
• The Synthesis and Pharmacological Evaluation of Adamantane-Derived Indoles: Cannabimimetic Drugs of Abuse
  作者：Samuel D. Banister、Shane M. Wilkinson、Mitchell Longworth、Jordyn Stuart、Nadine Apetz、Katrina English、Lance Brooker、Catrin Goebel、David E. Hibbs、Michelle Glass、Mark Connor、Iain S. McGregor、Michael Kassiou

  DOI：10.1021/cn400035r

  日期：2013.7.17

  Two novel adamantane derivatives, adamantan-1-yl (1-pentyl-1H-indo1-3-yl) methano ne (AB-001) and N-(adamtan-1-yl)-1-pentyl-1H-indole-3-carboxamide (SDB-001), were recently identified as cannabimimetic indoles of abuse. Conflicting anecdotal reports of the psychoactivity of AB-001 in humans, and a complete dearth of information about the bioactivity of SDB-001, prompted the preparation of AB-001, SDB-001, and several analogues intended to explore preliminary structure-activity relationships within this class. This study sought to elucidate which structural features of AB-001, SDB-001, and their analogues govern the cannabimimetic potency of these chemotypes in vitro and in vivo. All compounds showed similar full agonist profiles at CB1 (EC50 = 16-43 nM) and CB2 (EC50 = 29-216 nM) receptors in vitro using a FLIPR membrane potential assay, with the exception of SDB-002, which demonstrated partial agonist activity at CB2 receptors. The activity of AB-001, AB-002, and SDB-001 in rats was compared to that of Delta(9)-tetrahydrocannabinol (Delta(9)-THC) and cannabimimetic indole JWH-018 using biotelemetry. SDB-001 dose-dependently induced hypothermia and reduced heart rate (maximal dose 10 mg/kg) with potency comparable to that of Delta(9)-tetrahydrocannabinol (Delta(9)-THC, maximal dose 10 mg/kg), and lower than that of JWH-018 (maximal dose 3 mg/kg). Additionally, the changes in body temperature and heart rate affected by SDB-001 are of longer duration than those of Delta(9)-THC or JWH-018, suggesting a different pharmacokinetic profile. In contrast, AB-001, and its homologue, AB-002, did not produce significant hypothermic and bradycardic effects, even at relatively higher doses (up to 30 mg/kg), indicating greatly reduced potency compared to Delta(9)-THC, JWH-018, and SDB-001.
• New-generation azaindole-adamantyl-derived synthetic cannabinoids
  作者：Mitchell Longworth、Tristan A. Reekie、Karen Blakey、Rochelle Boyd、Mark Connor、Michael Kassiou

  DOI：10.1007/s11419-019-00466-1

  日期：2019.7

  each of the analogues regardless of the bicyclic core. For the first time in these SC structures, the bicyclic ring system was shown to have an impact on the cannabimimetic activities in the fluorometric assay of membrane potential. Analogues ranged from moderately potent at both CB1 and CB2 (e.g., AP4AIC EC50 = 160 nM and EC50 = 64 nM, respectively) to not active at either cannabinoid receptor (AP4AICA

  目的这项工作报告了新发现的一系列新的氮杂吲哚-金刚烷基衍生的合成大麻素（SC）的合成以及药理和分析数据。 方法使用有效且发散的合成方法合成每个SC，并通过电子电离质谱（EIMS）进行评估。使用荧光成像板读数器（FLIPR）分析进行每种化合物的仿拟活性。 结果所描述的EIMS方法和气相色谱保留时间能够有效区分每种类似物，而与双环核无关。在这些SC结构中，双环系统首次显示出对膜电位的荧光测定法对大麻模拟活性的影响。类似物的范围从在CB 1和CB 2上均适度有效（例如，AP4AIC EC 50  = 160 nM和EC 50  = 64 nM）到对任一大麻素受体（AP4AICA，AP5AICA和APIC）均无效。 结论进一步研究围绕这些双环核心的受体选择性可能证明对未来的治疗应用有用。