外四氢大麻酚 | 27179-28-8

• 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: 外四氢大麻酚
• 英文名称: Δ9(11)-tetrahydrocannabinol
• 英文别名: (6aR,10aR)-6a,7,8,9,10,10a-hexahydro-6,6-dimethyl-9-methylene-3-pentyl-6H-dibenzo[b,d]pyran-1-ol；(+/-)-delta7-Tetrahydrocannabinol；D11-THC；(6aR,10aR)-6,6-dimethyl-9-methylidene-3-pentyl-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-1-ol
• CAS: 27179-28-8
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: AOYYFUGUUIRBML-IAGOWNOFSA-N

物化性质

• 沸点：
  384.0±42.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)
• 闪点：
  9℃

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  外四氢大麻酚 在 盐酸 、 potassium 2-methylbutan-2-olate 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 0.5h， 生成 四氢大麻酚
  参考文献：
  名称：

  Addition and elimination of HCl to tetrahydrocannabinol isomers. A method for the preparation of stereospecifically 2H-labeled cannabinoids

  摘要：

  Addition of HCl gas to (-)Delta(8)-, (-)Delta(9)-, or (-)Delta(9,11)-THC solutions at -60 degrees C results in the formation of 9 alpha- and 9 beta-chlorohexahydrocannabinol (Cl-HHC). The addition appears to involve initial protonation of the double bond in the form of a bridged hydrogen cation followed by attack of the chloride anion at the most substituted 9-position. For both steps in the addition reaction the stereochemistry is dependent on the double bond position in the THC isomer. Elimination of HCl from each of the two addition products using potassium-tert-amylate leads exclusively to Delta(9)-THC in the case of 9 beta-Cl-HHC and to Delta(9,11)-THC in the case of 9 alpha-Cl-HHC. The individual addition products can be separated and used to obtain regio-and stereochemically H-2-isotopically labeled tetrahydrocannabinols which can be used in biophysical and biochemical studies.

  DOI：

  10.1002/(sici)1099-1344(199802)41:2<121::aid-jlcr55>3.0.co;2-s
• 作为产物：
  描述：

  1,3-二甲氧基-2-[(1R,6R)-3-甲基-6-丙-1-烯-2-基-1-环己-2-烯基]-5-戊基苯 在 potassium tert-butylate 、 氢溴酸 、 三溴化硼 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 13.17h， 生成 外四氢大麻酚
  参考文献：
  名称：

  Synthesis of (-)-.DELTA.9-6a,10a-trans-tetrahydrocannabinol. Boron trifluoride catalyzed arylation by a homocuprate

  摘要：

  DOI：

  10.1021/jo00177a044

文献信息

• Synthesis and pharmacological evaluation of ether and related analogs of .DELTA.8-, .DELTA.9-, and .DELTA.9,11-tetrahydrocannabinol
  作者：David R. Compton、W. Roy Prescott、Billy R. Martin、Craig Siegel、Patrick M. Gordon、Raj K. Razdan

  DOI：10.1021/jm00115a023

  日期：1991.11

  Additionally, novel analogues were evaluated for their ability to bind to the THC receptor site labeled by 3H-CP-55,940. None of the cannabinoid analogues were capable of attenuating the effects of delta 9-THC (3 mg/kg) in either the rat (doses up to 10 mg/kg) or in the mouse (doses up to 30 mg/kg). It also appears that the compounds with minimal in vivo activity are not mixed agonist/antagonists. These data would

  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。
• 13C-NMR. Spectra of Natural and Semi-synthetic Cannabinoids
  作者：Michael Binder、Ingo Franke、Burkhard Schmidt、Wolfgang Dietrich

  DOI：10.1002/hlca.19820650318

  日期：1982.5.5

  The 13C-NMR. spectra of one natural and ten semi-synthetic cannabinoids were analyzed in detail. Assignments of the signals are based on their chemical shifts, splitting patterns in 1H-off-resonance decoupling experiments and comparison with 13C-NMR. data of related cannabinoids. With some compounds final assignments were made by selective 1H-decoupling experiments and incremental calculations.

  的13 C-NMR。详细分析了一种天然大麻素和十种半合成大麻素的光谱。信号的分配基于其化学位移，1 H-off-共振去耦实验中的分裂模式以及与13 C-NMR的比较。相关大麻素的数据。对于某些化合物，最终的结果是通过选择性1 H解耦实验和增量计算得出的。
• Conversion of cannabidiol or delta-9 tetrahydrocannabinolic acid to delta-9 tetrahydrocannabinol and delta-8 tetrahydrocannabinol in nontoxic heterogeneous mixtures
  申请人：Pure Tonic Concentrates, LLC

  公开号：US10941131B1

  公开（公告）日：2021-03-09

  A solvent-free method for converting CBD or delta-9 THC-A to delta-9 THC and delta-8 THC includes adding CBD to a reaction vessel, streaming an inert gas through the reaction vessel, heating the CBD while stirring to melt the CBD, stirring the melting CBD, adding concentrated hydrochloric acid as a catalyst to the melting CBD while stirring, increasing the temperature over time to a temperature not to exceed the boiling point of reactants and products in the reaction vessel, holding the reaction vessel at a temperature less than the boiling point temperature for the reactants and products in the reaction vessel for an amount of time to allow the complete conversion of the CBD, and bubbling an inert gas into the reaction products to remove free ions of hydrogen and chloride. The CBD can be replaced in whole or in part by delta-9 THC-A as the reactant.

  使用无溶剂的方法将CBD或Δ-9 THC-A转化为Δ-9 THC和Δ-8 THC的步骤包括向反应容器中加入CBD，通过反应容器中通入惰性气体，加热CBD并搅拌以融化CBD，搅拌融化的CBD，向融化的CBD中加入浓盐酸作为催化剂并继续搅拌，随着时间的推移逐渐提高温度至不超过反应容器中反应物和产物的沸点的温度，将反应容器保持在低于反应容器中反应物和产物的沸点温度的温度下一段时间，以允许CBD的完全转化，并向反应产物中通入惰性气体以去除氢和氯离子。CBD可以全部或部分地被Δ-9 THC-A取代作为反应物。
• Metabolic Transformation of (3R, 4R)-?1(7)-Tetrahydrocannabinol by a Rat Liver Microsomal Preparation
  作者：Michael Binder、Uwe Barlage

  DOI：10.1002/hlca.19800630126

  日期：1980.1.23

  of the non-psychotropic cannabinoid (3R, 4R)Δ1(7)-tetrahydrocannabinol (1) (=Δ 1(7)-THC) was investigated in a rat liver microsomal preparation. The metabolites obtained from the incubation mixture were separated, purified and identified by 1H-NMR. spectroscopy and combined gas-liquid chromatography/mass spectrometry. Metabolites 3–10 are derived from Δ1(7)-THC (1) by mono-hydroxylation in the isoprenoid

  在大鼠肝微粒体制剂中研究了非精神性大麻素（3 R，4 R）Δ1 （7） -四氢大麻酚（1）（=Δ1 （7） -THC）的代谢。从温育混合物中获得的代谢物被分离，纯化并通过1 H-NMR鉴定。光谱和气液色谱/质谱联用。代谢物3-10通过类异戊二烯部分或分子侧链中的单羟基化作用衍生自Δ1 （7） -THC（1）。代谢物11–16在异戊二烯环和侧链中同时被羟基化。第三类，代谢物18–22是通过环氧乙烷环的水解从1,7-环氧化物17衍生而来的，这些代谢物中的三个在类异戊二烯部分或侧链中带有额外的羟基。详细讨论了代谢物的质谱，并提出了四氢大麻酚裂解的新规则。
• Novel synthesis of (−)-<i>trans</i>-Δ^9,11-tetrahydrocannabinol
  作者：Ali R. Banijamali、Alexandros Makriyannis

  DOI：10.1002/jhet.5570250324

  日期：1988.5

  Addition of hydrogen chloride gas to a solution of Δ8-tetrahydrocannabinol in dry dichloromethane at -60° in the presence of zinc chloride results in the formation of a higher concentration of 9-α-chlorohexa-hydrocannabinol (75%) than the thermodynamically more stable 9-β-chlorohexahydrocannabinol (25%). The two isomers can be separated by reverse-phase hplc. Elimination of hydrogen chloride from

  氯化氢气体的除了Δ的溶液8四氢大麻酚的无水二氯甲烷在-60℃在氯化锌的结果在9-α-chlorohexa-hydrocannabinol（75％）的高浓度的形成的存在比热力学上更稳定的9-β-氯六氢大麻酚（25％）。两种异构体可通过反相hplc分离。使用钾9-α-chlorohexa-hydrocannabinol氯化氢消除吨-amylate无水的条件下给出专门Δ 9,11中的65％总产率四氢大麻酚。