Structure of Cannabidiol. III. Reduction and Cleavage

Adams, Roger; Hunt, Madison; Clark, J. H.

doi:10.1021/ja01861a011

Cited by 19 publications

(11 citation statements)

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“…Early experiments on CBD characterization included both physical (polarimetry measurements) and chemical methods (oxidative degradation, ozonolysis, and partial hydrogenation reactions), as well as spectroscopy (UV/Vis and IR absorption spectra). [49][50][51] However, limited by the tools availablea tt he time, the group of Adamsw as wrong aboutt he positiono ft he endocyclic double bond of the terpenem oiety,s uggesting structure 6 without stereochemical assignments(Scheme 2). [52,53] According to the authors, the proposed structure of 6 would be susceptible to acid media to deliver two isomers (7 or 8), depending upon the conditions of acid-catalyzed isomerization (Scheme 2).…”

Section: First Attempts To Characterize Cbdmentioning

confidence: 99%

Cannabidiol Discovery and Synthesis—a Target‐Oriented Analysis in Drug Production Processes

Aguillón

Leão

Miranda

et al. 2021

Chemistry A European J

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Section: First Attempts To Characterize Cbdmentioning

confidence: 99%

Cannabidiol Discovery and Synthesis—a Target‐Oriented Analysis in Drug Production Processes

Aguillón

Leão

Miranda

et al. 2021

Chemistry A European J

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“…THC and CBD are the most important and studied plant cannabinoids. In 1940, CBD was first isolated from the plant [ 21 ]. In 1963 its structure was first described [ 22 ] and followed by its first identification as a crystal structure in 1977 [ 23 ].…”

Section: Cannabis Sativa L and Its Major Derivmentioning

confidence: 99%

Receptors and Channels Possibly Mediating the Effects of Phytocannabinoids on Seizures and Epilepsy

2020

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Epilepsy contributes to approximately 1% of the global disease burden. By affecting especially young children as well as older persons of all social and racial variety, epilepsy is a present disorder worldwide. Currently, only 65% of epileptic patients can be successfully treated with antiepileptic drugs. For this reason, alternative medicine receives more attention. Cannabis has been cultivated for over 6000 years to treat pain and insomnia and used since the 19th century to suppress epileptic seizures. The two best described phytocannabinoids, (−)-trans-Δ9-tetrahydrocannabinol (THC) and cannabidiol (CBD) are claimed to have positive effects on different neurological as well as neurodegenerative diseases, including epilepsy. There are different cannabinoids which act through different types of receptors and channels, including the cannabinoid receptor 1 and 2 (CB1, CB2), G protein-coupled receptor 55 (GPR55) and 18 (GPR18), opioid receptor µ and δ, transient receptor potential vanilloid type 1 (TRPV1) and 2 (TRPV2), type A γ-aminobutyric acid receptor (GABAAR) and voltage-gated sodium channels (VGSC). The mechanisms and importance of the interaction between phytocannabinoids and their different sites of action regarding epileptic seizures and their clinical value are described in this review.

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“…However, dimerization was detrimental for activity, and dimeric quinones were devoid of significant activity in PPARγ-activity assays. 23 Dimeric quinones are axially chiral, and, since enantiomeric cannabinoids can show markedly different profiles of bioactivity, 2 the one from CBG (CBGQ ( 23 )) was resolved by chromatography on a chiral-phase column packed with amylose-tris(5-chloro-2-methylphenylcarbamate). However, both the ( aR ) and the ( aS ) enantiomers turned out to be inactive.…”

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confidence: 99%

The Oxidation of Phytocannabinoids to Cannabinoquinoids

et al. 2020

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Spurred by a growing interest in cannabidiolquinone (CBDQ, HU-313, 2 ) as a degradation marker and alledged hepatotoxic metabolite of cannabidiol (CBD, 1 ), we performed a systematic study on the oxidation of CBD ( 1 ) to CBDQ ( 2 ) under a variety of experimental conditions (base-catalyzed aerobic oxidation, oxidation with metals, oxidation with hypervalent iodine reagents). The best results in terms of reproducibility and scalability were obtained with λ 5 -periodinanes (Dess-Martin periodinane, 1-hydroxy-1λ 5 ,2-benziodoxole-1,3-dione (IBX), and SIBX, a stabilized, nonexplosive version of IBX). With these reagents, the oxidative dimerization that plagues the reaction under basic aerobic conditions was completely suppressed. A different reaction course was observed with the copper(II) chloride-hydroxylamine complex (Takehira reagent), which afforded a mixture of the hydroxyiminodienone 11 and the halogenated resorcinol 12 . The λ 5 -periodinane oxidation was general for phytocannabinoids, turning cannabigerol (CBG, 18 ), cannabichromene (CBC, 10 ), and cannabinol (CBN, 19 ) into their corresponding hydroxyquinones ( 20 , 21 , and 22 , respectively). All cannabinoquinoids modulated to a various extent peroxisome proliferator-activated receptor gamma (PPAR-γ) activity, outperforming their parent resorcinols in terms of potency, but the iminoquinone 11 , the quinone dimers 3 and 23 , and the haloresorcinol 12 were inactive, suggesting a specific role for the monomeric hydroxyquinone moiety in the interaction with PPAR-γ.

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Structure of Cannabidiol. III. Reduction and Cleavage

Cited by 19 publications

References 0 publications

Cannabidiol Discovery and Synthesis—a Target‐Oriented Analysis in Drug Production Processes

Cannabidiol Discovery and Synthesis—a Target‐Oriented Analysis in Drug Production Processes

Receptors and Channels Possibly Mediating the Effects of Phytocannabinoids on Seizures and Epilepsy

The Oxidation of Phytocannabinoids to Cannabinoquinoids

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