(6aR,10aR)-6,6,9-三甲基-3-丙基-6A,7,10,10A-四氢-6H-苯并[c]苯并吡喃-1-醇 | 31262-38-1

• 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: (6aR,10aR)-6,6,9-三甲基-3-丙基-6A,7,10,10A-四氢-6H-苯并[c]苯并吡喃-1-醇
• 英文名称: Propyl-delta(8)-tetrahydrocannabiol
• 英文别名: 3-norpentyl-3-propyl-Δ⁸-tetrahydrocannabinol；4'-propyl-(-)-trans-Δ⁸-tetrahydrocannabinol；Δ⁸‐tetrahydrocannabivarin；Δ(8)-tetrahydrocannabivarin；Δ⁸‐THCV；Δ(8)-THCV；Propyl-delta(8)-tetrahydrocannabinol；(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
• CAS: 31262-38-1
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: CDBDULHNWQRYSY-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6aR,10aR)-6,6,9-三甲基-3-丙基-6A,7,10,10A-四氢-6H-苯并[c]苯并吡喃-1-醇 以 异丙醇 为溶剂， 反应 4.5h， 以26%的产率得到(-)-3-norpentyl-3-propyl-Δ^9,11-tetrahydrocannabinol
  参考文献：
  名称：

  δ8，δ9-和δ9,11-四氢大麻酚的醚及相关类似物的合成及药理学评估。

  摘要：

  这项研究的主要目的是合成一系列大麻类药物的醚类似物，并评估它们在小鼠或大鼠中的激动剂和拮抗剂药理特性。使用多重评价程序（运动活性，甩尾潜伏期，体温过低，环不动）对小鼠的激动剂和拮抗剂活性进行评估，并在判别性刺激范式中确定大鼠的活性。另外，评价了新的类似物结合由3H-CP-55,940标记的THC受体位点的能力。大麻素类似物均不能在大鼠（最高剂量10 mg / kg）或小鼠（最高剂量30 mg / kg）中减弱δ9-THC（3 mg / kg）的作用。还似乎具有最小体内活性的化合物不是混合的激动剂/拮抗剂。这些数据表明酚羟基对于受体识别（结合）和体内效力很重要。另外，已经发现先前被认为是无活性的大麻素甲基醚产生有限的活性。最后，数据表明，δ9,11-THC比以前的报告更有效，并且确实具有药理活性。

  DOI：

  10.1021/jm00115a023
• 作为产物：
  描述：

  次大麻二酚 在 对甲苯磺酸 作用下， 反应 2.0h， 以96%的产率得到(6aR,10aR)-6,6,9-三甲基-3-丙基-6A,7,10,10A-四氢-6H-苯并[c]苯并吡喃-1-醇
  参考文献：
  名称：

  Comparative topical anti-inflammatory activity of cannabinoids and cannabivarins

  摘要：

  A selection of seven phytocannabinoids representative of the major structural types of classic cannabinoids and their corresponding cannabivarins was investigated for in vivo topical anti-inflammatory activity in the Croton oil mouse ear dermatitis assay. Differences in the terpenoid moiety were far more important for anti-inflammatory activity than those at the C-3 alkyl residue, suggesting the involvement not only of cannabinoid receptors, but also of other inflammatory end-points targeted by phytocannabinoids. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2010.04.009

文献信息

• A Revised Modular Approach to (-)-<i>trans</i> -Δ⁸ -THC and Derivatives Through Late-Stage Suzuki-Miyaura Cross-Coupling Reactions
  作者：Victor R. L. J. Bloemendal、Daan Sondag、Hidde Elferink、Thomas J. Boltje、Jan. C. M. van Hest、Floris P. J. T. Rutjes

  DOI：10.1002/ejoc.201900059

  日期：2019.3.31

  various synthetic (–)‐trans‐Δ8‐THC derivatives through late‐stage Suzuki–Miyaura cross‐coupling reactions is disclosed. Ten derivatives were synthesized allowing both sp2‐ and sp3‐hybridized cross‐coupling partners with minimal β‐hydride elimination. Importantly, we demonstrate that a para‐bromo‐substituted THC scaffold for Suzuki–Miyaura cross‐coupling reactions has been initially reported incorrectly

  公开了通过后期 Suzuki-Miyaura 交叉偶联反应对各种合成 (-)-trans-Δ8-THC 衍生物进行修改的模块化方法。合成了 10 种衍生物，允许 sp2 和 sp3 杂交交叉偶联伙伴，消除最小的 β-氢化物。重要的是，我们证明了用于 Suzuki-Miyaura 交叉偶联反应的对位溴取代的 THC 支架最初在最近的文献中被错误地报道。
• Isolation and Characterization of Impurities in Commercially Marketed Δ⁸-THC Products
  作者：Mohamed M. Radwan、Amira S. Wanas、Waseem Gul、Elsayed A. Ibrahim、Mahmoud A. ElSohly

  DOI：10.1021/acs.jnatprod.2c01008

  日期：——

  Δ9-THC (11). The chemical structures of the purified compounds were determined using several spectroscopic methods, including 1D (1H, 13C, and DEPT-135) and 2D (COSY, HMQC, HMBC, and NOESY) NMR, LC–MS, and GC-MS. Other naturally occurring cannabinoids and impurities were also identified in GC-MS chromatograms but were not isolated. These were cannabidiol (CBD, 12), cannabinol (CBN, 13), hexahydrocannabinol

  使用 GC-MS对几种含有 Δ 8 -四氢大麻酚 (Δ 8 -THC) 作为主要成分的商业产品进行定性分析，结果鉴定出了几种杂质以及 Δ 8 -THC。为了尝试分离和鉴定这些杂质，选择商业 Δ 8 -THC 馏出物进行分离工作。使用多种色谱技术分离出十一种杂质，并确定了它们的化学结构。这些包括 Δ 4,8-异-四氢大麻酚 ( 1 ) 、Δ 4-异-四氢大麻酚 ( 2 )、Δ 8-顺式-异-四氢大麻酚 ( 3 )、4,8-环氧-异-四氢大麻酚 ( 4 )、8-羟基-异-四氢大麻酚 ( 5 )、9β-羟基六氢大麻酚 ( 6 )、9α-羟基六氢大麻酚 ( 7 )、异-四氢大麻呋喃 ( 8 )、大麻西群 (CBT, 9 )、橄榄醇 ( 10 ) 和 Δ 9 -THC ( 11 )。使用多种光谱方法确定纯化化合物的化学结构，包括 1D ( 1 H, 13C、DEPT-135）和 2D（COSY、HMQC、HMBC
• TOPICAL ANTIBIOTIC
  申请人：Concept Matrix Solutions

  公开号：US20210093690A1

  公开（公告）日：2021-04-01

  Provided herein is a topical antibiotic composition that includes an external antibiotic agent, one or more pharmaceutically acceptable excipients, and at least one of a cannabinoid, terpene, and flavonoid. Also provided is a method that includes topically administering to a skin surface of a subject (e.g., human) the topical antibiotic composition.
• STABLE FORMULATIONS OF DRONABINOL
  申请人：TRYAGx Labs Inc.

  公开号：US20210251947A1

  公开（公告）日：2021-08-19

  Described herein are formulations, methods of manufacturing, and methods of treatment using formulations of cannabinoids that are stable at room temperature for at least about one to two years. In one embodiment, the composition is an oxidatively stable formulation of dronabinol.
• CARTRIDGE FOR VAPOR-PHASE CANNABINOID REACTIONS WITHIN A DEVICE
  申请人：Canopy Growth Corporation

  公开号：US20220218653A1

  公开（公告）日：2022-07-14

  Disclosed herein is a cartridge for a vape device. The cartridge comprises a housing defining an inlet, an outlet, and an interior chamber that is position between the inlet and the outlet. The inlet, the outlet, and the interior chamber are fluidly connected by a flow path, and the inlet is configured to receive a first cannabinoid. The cartridge also comprises a Lewis-acidic heterogeneous reagent positioned in the interior chamber such that when the flow path passes through the interior chamber, at least a portion of the flow path contacts the Lewis-acidic heterogeneous reagent. The Lewis-acidic heterogeneous reagent has an acidity metric that surpasses a threshold acidity metric for the first cannabinoid such that contact between the Lewis-acidic heterogeneous reagent and the first cannabinoid under reaction conditions defined by a contact temperature and a contact time converts at least a portion of the first cannabinoid into a second cannabinoid.