1-(cyclobutylmethyl)-N-(2-phenylpropan-2-yl)-1H-indole-3-carboxamide | 2571070-88-5

• 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: 1-(cyclobutylmethyl)-N-(2-phenylpropan-2-yl)-1H-indole-3-carboxamide
• 英文别名: Cumyl-cbmica；1-(cyclobutylmethyl)-N-(2-phenylpropan-2-yl)indole-3-carboxamide
• CAS: 2571070-88-5
• 化学式: C₂₃H₂₆N₂O
• 分子量: 346.472
• InChiKey: INXXQNIOWMOYEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  34.03
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1-(Cyclobutylmethyl)indole 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 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 2.0h， 生成 1-(cyclobutylmethyl)-N-(2-phenylpropan-2-yl)-1H-indole-3-carboxamide
  参考文献：
  名称：

  Comprehensive Characterization of a Systematic Library of Alkyl and Alicyclic Synthetic Cannabinoids Related to CUMYL-PICA, CUMYL-BUTICA, CUMYL-CBMICA, and CUMYL-PINACA

  摘要：

  DOI：

  10.1021/acschemneuro.2c00408

文献信息

• Synthesis and <i>in Vitro</i> Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA
  作者：Annelies Cannaert、Eric Sparkes、Edward Pike、Jia Lin Luo、Ada Fang、Richard C. Kevin、Ross Ellison、Roy Gerona、Samuel D. Banister、Christophe P. Stove

  DOI：10.1021/acschemneuro.0c00644

  日期：2020.12.16

  Synthetic cannabinoid receptor agonists (SCRAs) are an evolving class of new psychoactive substances (NPS) with structurally diverse compounds emerging each year. Due to the rapid pace at which these drugs enter the market, there is often little or nil information regarding the pharmacology of these substances despite widespread human use. In this study, 12 recently emerged SCRAs (reported between 2018 and 2020) were synthesized, analytically characterized, and pharmacologically evaluated using a live cell-based nanoluciferase complementation reporter assay that monitors in vitro cannabinoid receptor type 1 (CB1) activation via its interaction with β-arrestin 2 (βarr2). All synthesized SCRAs acted as agonists of CB1, although differences in potency (EC50 = 2.33-5475 nM) and efficacy (Emax = 37-378%) were noted, and several structure-activity relationships were identified. SCRAs featuring indazole cores (EC50 = 2.33-159 nM) were generally of equal or greater potency than indole analogues (EC50 = 32.9-330 nM) or 7-azaindole derivatives (EC50 = 64.0-5475 nM). Interestingly, with the exception of APP-BINACA (Emax = 75.7%) and 5F-A-P7AICA (Emax = 37.4%), all SCRAs showed greater efficacy than the historical SCRA JWH-018 to which responses were normalized (Emax = 142-378%). The most potent CB1 agonists in the study were ADB-BINACA (EC50 = 6.36 nM), 4F-MDMB-BINACA (EC50 = 7.39 nM), and MDMB-4en-PINACA (EC50 = 2.33 nM). Notably, all of these SCRAs featured an indazole core as well as a "bulky" tert-butyl moiety in the pendant amino acid side chain. This study confirms that recently detected SCRAs 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA were all able to activate the CB1 receptor in vitro, albeit to different extents, and are potentially psychoactive in vivo. These results indicate that further evaluation of these widely used NPS is warranted to better understand the risks associated with human consumption of these drugs.
• NUCLEAR MAGNETIC RESONANCE IMPLEMENTED SYNTHETIC INDOLE AND INDAZOLE CANNABINOID DETECTION, IDENTIFICATION, AND QUANTIFICATION
  申请人：HOFSTRA UNIVERSITY

  公开号：US20220026380A1

  公开（公告）日：2022-01-27

  The present invention provides a method for detecting synthetic indole and indazole cannabinoids in a sample known or suspected to contain a synthetic indole or indazole cannabinoid. A deuterated solvent is added to the solid sample, creating a suspension. The suspension is mixed to release the cannabinoid from the solid sample. The suspension is subject to a NMR spectroscopy process to produce a sample NMR spectrum. The synthetic cannabinoid is detected in the suspension by analysis of the sample NMR spectrum. When one-dimensional proton NMR is used, detection of a first peak between 8.00 and 8.50 ppm and a second peak between 4.00 and 4.40 ppm, indicates the presence of a synthetic indole or indazole cannabinoid. When two-dimensional Correlation Spectroscopy (COSY) NMR is used, detection of a first spot between 6.50 and 9.00 ppm and a second spot between 1.50 and 4.50 ppm indicates the presence of a synthetic indole or indazole cannabinoid. The method is performed in the absence of chromatography and optionally, may be used to quantify the amount of synthetic cannabinoid.