大麻酚单甲醚 | 41935-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 大麻酚单甲醚
• 英文名称: cannabinol monomethyl ether
• 英文别名: cannabinol methyl ether；cannabinol methylether；CBN monomethyl ether；methyl cannabinol；CBNM；1-methoxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene；1-methoxy-6,6,9-trimethyl-3-pentylbenzo[c]chromene
• CAS: 41935-92-6
• 化学式: C₂₂H₂₈O₂
• 分子量: 324.463
• InChiKey: YEDIZIGYIMTZKP-UHFFFAOYSA-N

物化性质

• 沸点：
  456.7±24.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：50mg/mL； DMSO：50mg/mL； DMSO:PBS(pH 7.2)(1:3)：250μg/ml；乙醇：30mg/mL；甲醇：30mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  大麻酚单甲醚 在 水 、 氢碘酸 、 乙酸酐 作用下， 反应 7.0h， 以77%的产率得到大麻酚
  参考文献：
  名称：

  大麻素的环三聚途径。

  摘要：

  使用微波介导的[2 + 2 + 2]环三聚反应作为关键步骤，合成了大麻素类的三个成员：大麻酚，大麻醇甲醚和大麻醇。这种方法提供了高水平的合成灵活性，可轻松合成大麻素类似物。

  DOI：

  10.1021/ol800589e
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以17.6 mg的产率得到大麻酚单甲醚
  参考文献：
  名称：

  大麻素的环三聚途径。

  摘要：

  使用微波介导的[2 + 2 + 2]环三聚反应作为关键步骤，合成了大麻素类的三个成员：大麻酚，大麻醇甲醚和大麻醇。这种方法提供了高水平的合成灵活性，可轻松合成大麻素类似物。

  DOI：

  10.1021/ol800589e

文献信息

• Efficacy of Cannabinoids in a Pre-Clinical Drug-Screening Platform for Alzheimer’s Disease
  作者：David Schubert、Devin Kepchia、Zhibin Liang、Richard Dargusch、Joshua Goldberg、Pamela Maher

  DOI：10.1007/s12035-019-1637-8

  日期：2019.11

  Finding a therapy for Alzheimer’s disease (AD) is perhaps the greatest challenge for modern medicine. The chemical scaffolds of many drugs in the clinic today are based upon natural products from plants, yet Cannabis has not been extensively examined as a source of potential AD drug candidates. Here, we determine if a number of non-psychoactive cannabinoids are neuroprotective in a novel pre-clinical AD and neurodegeneration drug-screening platform that is based upon toxicities associated with the aging brain. This drug discovery paradigm has yielded several compounds in or approaching clinical trials for AD. Eleven cannabinoids were assayed for neuroprotection in assays that recapitulate proteotoxicity, loss of trophic support, oxidative stress, energy loss, and inflammation. These compounds were also assayed for their ability to remove intraneuronal amyloid and subjected to a structure-activity relationship analysis. Pairwise combinations were assayed for their ability to synergize to produce neuroprotective effects that were greater than additive. Nine of the 11 cannabinoids have the ability to protect cells in four distinct phenotypic neurodegeneration screening assays, including those using neurons that lack CB1 and CB2 receptors. They are able to remove intraneuronal Aβ, reduce oxidative damage, and protect from the loss of energy or trophic support. Structure-activity relationship (SAR) data show that functional antioxidant groups such as aromatic hydroxyls are necessary but not sufficient for neuroprotection. Therefore, there is a need to focus upon CB1 agonists that have these functionalities if neuroprotection is the goal. Pairwise combinations of THC and CBN lead to a synergistic neuroprotective interaction. Together, these results significantly extend the published data by showing that non-psychoactive cannabinoids are potential lead drug candidates for AD and other neurodegenerative diseases.

  寻找阿尔茨海默病（AD）的治疗方法可能是现代医学面临的最大挑战。如今临床上许多药物的化学支架都是基于植物的天然产物，但大麻尚未作为潜在 AD 候选药物的来源进行广泛研究。在这里，我们根据与大脑老化相关的毒性，确定了一些非精神活性大麻素在新型临床前 AD 和神经退行性疾病药物筛选平台中是否具有神经保护作用。这种药物发现范式已经产生了几种正在进行或即将进行 AD 临床试验的化合物。在概括蛋白质毒性、营养支持丧失、氧化应激、能量损失和炎症的测定中，对十一种大麻素进行了神经保护作用。还测定了这些化合物去除神经元内淀粉样蛋白的能力，并进行结构-活性关系分析。分析了成对组合的协同作用能力，以产生大于相加的神经保护作用。 11 种大麻素中的 9 种能够在四种不同表型神经变性筛选试验中保护细胞，包括使用缺乏 CB1 和 CB2 受体的神经元的试验。它们能够去除神经元内的 Aβ，减少氧化损伤，并防止能量或营养支持的损失。构效关系（SAR）数据表明，芳香羟基等功能性抗氧化基团对于神经保护是必要的，但还不够。因此，如果神经保护是目标，则需要关注具有这些功能的 CB1 激动剂。 THC 和 CBN 的配对组合可产生协同的神经保护相互作用。总之，这些结果显着扩展了已发表的数据，表明非精神活性大麻素是 AD 和其他神经退行性疾病的潜在主要候选药物。
• Cannabinoid composition and products including α-tocopherol
  申请人：Constance Therapeutics, Inc.

  公开号：US10238745B2

  公开（公告）日：2019-03-26

  A cannabinoid composition having an excipient including α-tocopherol and at least one isolated cannabinoid having a purity of greater than 80%. The α-tocopherol inhibits oxidation, regulates viscosity of the composition, and improves bioavailability of the cannabinoid. The composition includes a carrier oil mixed with the excipient and cannabinoid. In one embodiment, the at least one cannabinoid is an isolated cannabinoid having a greater than 80% purity, and preferably greater than 90% purity. The at least one cannabinoid is selected from the group consisting of phytocannabinoids, endocannabinoids, synthetic cannabinoids, and combinations thereof. The cannabinoid may be derived from plants other than cannabis sativa, or synthesized from fungi, bacteria, yeast or other synthetic method. Preferably the α-tocopherol comprises at least 10% w/w of the composition.

  一种大麻素组合物，其赋形剂包括α-生育酚和至少一种纯度大于 80% 的分离大麻素。α-生育酚可抑制氧化，调节组合物的粘度，提高大麻素的生物利用度。组合物包括与赋形剂和大麻素混合的载体油。在一个实施方案中，至少一种大麻素是分离出来的大麻素，纯度大于 80%，最好大于 90%。至少一种大麻素选自植物大麻素、内源性大麻素、合成大麻素及其组合组成的组。大麻素可以从大麻以外的植物中提取，也可以从真菌、细菌、酵母或其他合成方法中合成。α-生育酚最好至少占组合物重量的 10%。
• Cannabis oil extracts and compositions
  申请人：CONSTANCE THERAPEUTICS, INC.

  公开号：US10406186B2

  公开（公告）日：2019-09-10

  The present invention provides cannabis oil extracts and compositions thereof, including cannabis oil compositions containing vitamin E, and methods for preparing the extracts and compositions. In some embodiments, the present invention provides a method for preparing a cannabis oil extract comprising eluting cannabinoids from cannabis plant material with a solvent to produce an eluate, filtering the eluate with a filter to produce a filtrate, evaporating the solvent from the filtrate with a distiller to produce a distillate, and purging the distillate under conditions sufficient to remove residual solvent, thereby preparing the extract. In some embodiments, the method further includes mixing a quantity of vitamin E with the extract to produce a cannabis oil composition.

  本发明提供了大麻油提取物及其组合物，包括含有维生素 E 的大麻油组合物，以及制备提取物和组合物的方法。在一些实施方案中，本发明提供了一种制备大麻油提取物的方法，包括用溶剂从大麻植物材料中洗脱大麻素以产生洗脱液，用过滤器过滤洗脱液以产生滤液，用蒸馏器蒸发滤液中的溶剂以产生蒸馏物，在足以除去残留溶剂的条件下净化蒸馏物，从而制备提取物。在某些实施方案中，该方法还包括将一定量的维生素 E 与萃取物混合，制成大麻油组合物。
• Breeding, production, processing and use of medical cannabis
  申请人：BIOTECH INSTITUTE, LLC

  公开号：US10441617B2

  公开（公告）日：2019-10-15

  The invention provides compositions and methods for the breeding, production, processing and use of medical cannabis.

  本发明提供了用于培育、生产、加工和使用医用大麻的组合物和方法。
• Bioactive concentrates and uses thereof
  申请人：SC LABORATORIES, INC.

  公开号：US10792318B2

  公开（公告）日：2020-10-06

  The present invention relates to concentrates obtained from extraction from Cannabis, preferably cannabinoid and/or terpene concentrates, and formulation of the concentrates, particularly for use for direct vaporization, infusion into edible matrices, in electronic inhalation devices, and as nutraceuticals.

  本发明涉及从大麻中提取的浓缩物，最好是大麻素和/或萜类浓缩物，以及浓缩物的配方，特别是用于直接汽化、注入可食用基质、电子吸入装置和作为营养保健品。