dehydroxylcannabidiol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: dehydroxylcannabidiol
• 英文别名: 5-Desoxy-delta9-tetrahydrocannabinol；2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylphenol
• 化学式: C₂₁H₃₀O
• 分子量: 298.469
• InChiKey: OANGEIYPAQYPQV-AZUAARDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  dehydroxylcannabidiol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到四氢大麻酚
  参考文献：
  名称：

  WO2006/133941

  摘要：

  公开号：
• 作为产物：
  描述：

  甜橙提取物 在 三氟化硼乙醚 、 双氧水 、 magnesium sulfate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， -78.0~180.0 ℃ 、133.32 Pa 条件下， 反应 23.0h， 生成 dehydroxylcannabidiol
  参考文献：
  名称：

  Improved accessibility to the desoxy analogues of Δ9-tetrahydrocannabinol and cannabidiol

  摘要：

  Desoxy analogues of Delta(9)-tetrahydrocannabinol (THC) and cannabidiol (CBD) have been reported to provide a novel mode of analgesia whilst avoiding the psychotropic side effects associated with most cannabinoid drugs. A detailed and improved synthesis of desoxy THC, desoxy CBD and didesoxy CBD is reported here. The key improvements include a concentration-dependent boron trifluoride mediated electrophilic aromatic substitution which was used to synthesize both THC and CBD analogues. The synthetic route is general and could be applied to the development of a library of modified desoxy THC and desoxy CBD analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.080

文献信息

• The design, synthesis and testing of desoxy-CBD: Further evidence for a region of steric interference at the cannabinoid receptor
  作者：P.H. Reggio、R.D. Bramblett、H. Yuknavich、H.H. Seltzman、D.N. Fleming、S.R. Fernando、L.A. Stevenson、R.G. Pertwee

  DOI：10.1016/0024-3205(95)00185-9

  日期：1995.5

  steric interference at the CB1 receptor [P.H. Reggio, A.M. Panu, S. Miles J. Med. Chem. 36, 1761-1771 (1993)] in three dimensions using the Active Analog Approach. We report here a conformational analysis of CBD which, in turn, led to the design of a new analog, desoxy-CBD. Modeling results for desoxy-CBD predict that this compound is capable of clearing the region of steric interference by expending 3

  据报道，大麻二酚CBD是大麻的非精神活性成分，对大脑中的大麻素CB1受体结合位点基本上没有亲和力。关于CBD对大麻素CB1受体缺乏亲和力的假设是，CBD无法清除CB1受体处的空间干扰区域，因此无法与该受体结合。我们先前已经表征了在CB1受体处的空间干扰区域[PH Reggio，AM Panu，S. Miles J. Med。化学 36，1761-1771（1993）]在三个维度上使用主动模拟方法。我们在这里报告了CBD的构象分析，进而导致了新的类似物desoxy-CBD的设计。脱氧CBD的建模结果表明，该化合物能够通过消耗3清除空间干扰区域。能量为64 kcal / mol，而CBD则为12.39 kcal / mol。脱氧-CBD是通过DMF-二戊基缩醛介导的3-戊基苯酚与p-mentha-2,8-dien-1-ol缩合合成的。在小鼠输精管测定中发现了脱氧-CBD充当部分激动剂，据报道该
• POLYCANNABINOIDS, COMPOUNDS, COMPOSITIONS AND METHODS OF USE
  申请人：University of Connecticut

  公开号：US20210322365A1

  公开（公告）日：2021-10-21

  Polymers comprising a plurality of cannabinoids, methods of preparation thereof, and methods of use to treat a number of disease conditions are reported. Also provided are polymer coatings, films, fibers, and non-woven fabrics for a variety of topical applications including stents, bandages, sutures, and transdermal patches.

  本文报告了包含多种大麻素的聚合物，其制备方法以及用于治疗多种疾病状况的方法。同时，还提供了用于各种局部应用的聚合物涂层、膜、纤维和无纺布，包括支架、绷带、缝合线和经皮贴片。
• [EN] CBD CANNABINOIDS AND CBD CANNABINOID ANALOGUES<br/>[FR] CANNABINOÏDES CBD ET ANALOGUES DE CANNABINOÏDES CBD
  申请人：BOTANIX PHARMACEUTICALS LTD

  公开号：WO2022133544A1

  公开（公告）日：2022-06-30

  Cannabidiol (CBD) cannabinoids and CBD cannabinoid analogues with, inter alia, antimicrobial activity, synthetic methods for the preparation thereof and medical uses and formulations containing same.

  大麻二酚（CBD）大麻素及CBD类似物具有抗微生物活性，其制备的合成方法以及含有其的医疗用途和制剂。
• Cholesterol regulates cannabinoid analgesia through glycine receptors
  作者：Lei Yao、Chengyuan Liu、Ning Wang、Feng Du、Sijia Fan、Yujun Guo、Li Zhang、Yang Pan、Wei Xiong

  DOI：10.1016/j.neuropharm.2020.108242

  日期：2020.10

  Cholesterol plays vital roles in many central physiological and pathological processes. As a key component in the cell membrane, cholesterol can regulate a variety of ion channels, including ligand-gated ion channels (LGICs). However, relatively little is known about the molecular detail and in vivo consequence of cholesterol-LGIC interaction. Here, we reveal that membrane cholesterol depletion significantly inhibits the potentiating effects of dehydroxylcannabidiol (DH-CBD) on glycine-activated currents (I-Gly) in HEK 293T cells expressing alpha 1/alpha 3 glycine receptors (GlyRs). Simvastatin considerably decreases cholesterol levels and DH-CBD-induced potentiation of I-Gly in the spinal cord of mice. Simvastatin also significantly decreases DH-CBD analgesia in acute and chronic pain of mice. The cholesterol levels in the dorsal horn of spinal cord, measured by mass spectrometry imaging, are specifically correlated with cannabinoid potentiation of spinal GlyRs and cannabinoid-induced analgesia. These findings suggest that spinal cholesterol is critical for the efficacy of glycinergic cannabinoid-induced analgesia.
• PROPYL CANNABINOID HEMP PLANTS, METHODS OF PRODUCING AND METHODS OF USING THEM
  申请人：Biotech Institute, LLC

  公开号：US20210045311A1

  公开（公告）日：2021-02-18

  The invention provides compositions and methods for the breeding, production, processing and use of Specialty Cannabis , including new hemp varieties comprising high levels of propyl cannabinoids with low THC content Cannabinoid compositions comprising high levels of propyl cannabinoids with low THC content are also disclosed.