Synthese und Chiralität des (‐)‐Cannabidiols Vorläufige Mitteilung

Petrzilka, Th.; Haefliger, W.; Sikemeier, C.; Ohloff, G.; Eschenmoser, Albert

doi:10.1002/hlca.19670500235

Cited by 78 publications

(34 citation statements)

References 18 publications

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“…In the case of opioids, morphine can either be extracted from P. somniferum or created by full chemical synthesis (Gates and Tschudi, 1956; Mechoulam and Hanuš, 2000; Novak et al., 2000). The same goes with molecules structurally identical to naturally occurring phytocannabinoids such as dronabinol or cannabidiol (CBD is the INN of (–)-CBD, whether natural or synthetic) that are designed in vitro without involving initial plant material (Adam Ametovski and Lupton, 2019; Mechoulam and Gaoni, 1965; Petrzilka et al., 1967; Razdan et al., 1974; Trost and Dogra, 2007). Analytically indistinguishable, fully synthesised in vitro phytocannabinoids and naturally obtained in vivo phytocannabinoids were not distinguished by the ECDD which considers them in all points pharmacologically identical (ECDD, 2019: 54–55; Riboulet-Zemouli and Krawitz, 2019).…”

Section: Resultsmentioning

confidence: 99%

“…Eighty years ago, Adams et al (1940) were the first to synthesise a cannabinoid compound ex vivo: the phytocannabinoid CBN (see Mechoulam and Hanu s, 2000;Pertwee, 2006). The first compounds to be named 'synthetic cannabinoid' in the 1960s were all closely related to the molecules found in C. sativa, either phytocannabinoids obtained in vitro or closely related byproducts, obtained during attempts to synthesise and describe naturally occurring phytocannabinoids (Bow and Rimoldi, 2016;Fahrenholtz et al, 1967;Mechoulam and Gaoni, 1965;Mechoulam and Hanu s, 2000;Pertwee, 2006;Petrzilka et al, 1967;Razdan and Zitko, 1969). Hence their definition by the negative insofar they were, by then, the only non-natural, not wholly-phyto cannabinoids.…”

Section: A Metachemistry Of Cannabinoids (And Beyond)mentioning

confidence: 99%

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‘Cannabis’ ontologies I: Conceptual issues with Cannabis and cannabinoids terminology

Riboulet-Zemouli¹

2020

Drug Science, Policy and Law

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Objective Identify a coherent nomenclature for Cannabis sativa L. derived products and their analogues. Design Research undertaken in parallel to the three-year assessment of Cannabis derivatives by the World Health Organisation. The scope is limited to Cannabis products intended for human incorporation (internal and topical consumption). Primarily embedded in pharmacognosy, the study incorporates a wide range of scholarly and grey literature, folk knowledge, archives, pharmacopœias, international law, field pharmacy, clinical and herbal medicine data, under a philosophical scrutiny. Generic and Cannabis-specific nomenclatural frames are compared to determine the extent to which they coincide or conflict. Results All lexica reviewed use weak, ambiguous, or inconsistent terms. There is insufficient scientific basis for terms and concepts related to Cannabis at all levels. No sound classification exists: current models conflict by adopting idiosyncratic, partial, outdated, or utilitarian schemes to arrange the extraordinarily numerous and diverse derivatives of the C. sativa plant. In law and policy, no clear or unequivocal boundary between herbal and non-herbal drugs, nor natural and synthetic cannabinoids was found; current nomenclatures need updates. In science, the botanical Cannabis lexicon overlooks parthenocarpy, and wide disagreement remains as to the taxonomy and systematics of the plant; chemical research should address differences in kinds between synthetic cannabinoids; pharmacopœias include little information related to Cannabis, and disagree on broader classes of herbal medicines, virtually failing to embrace many known Cannabis medicines. Since existing products and compounds fail to be categorised in an evidence-based manner, confusions will likely increase as novel cannabinoid compounds, genetic and biotechnological modifications surge. Conclusions The lack of clarity is comprehensive: for patients, physicians, and regulators. This study proposes an update of terms at several levels. It points at gaps in morphological descriptions in botany and pharmacognosy and a need for a metaphysical address of cannabinoids. Methods of obtention are identified as a common criterion to distinguish products; the way forward suggests a mutually exclusive nomenclatural pattern based on the smallest common denominator of obtention methods. In the context of a swelling number of Cannabis products being consumed (be it via medical prescription, adult-use, ‘hemp’ foodstuff and cosmetics, or other purposes), this study can assist research, contribute to transparent labelling of products, consumer safety and awareness, pharmacovigilance, medical standards of care, and an update of prevention and harm reduction approaches. It can also better inform regulatory policies surrounding C. sativa, its derivatives, and other cannabinoid-containing products.

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Section: Resultsmentioning

confidence: 99%

Section: A Metachemistry Of Cannabinoids (And Beyond)mentioning

confidence: 99%

‘Cannabis’ ontologies I: Conceptual issues with Cannabis and cannabinoids terminology

Riboulet-Zemouli¹

2020

Drug Science, Policy and Law

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“…Researchers have already used several synthetic strategies to deliver the desired CBD molecule, in both racemic [78,110,111] and enantioselective [112][113][114][115][116][117][118][119] ways (Scheme 8). [112][113][114][115][116][117][118][119] These strategies include, as key steps, reactions such as Friedel-Crafts alkylation, [120][121][122][123] Diels-Alder cycloaddition, [111] anion-ic addition mediated by strongb ases [78] and/oro rganometallic species, [118,124] stereodivergent dual catalysis reactions, [119,125] and biotechnological synthesis. [112] 4.1.…”

Section: General Aspects Of Cbd Synthesismentioning

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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“…In 1965, Petrzilka et al presented a stereoselective synthesis method for (-)-CBD. The (-)-cannabidiol can be obtained through olivetol with 4-isopropenyl-1-methyl-2-cyclohexene-1-ol in the presence of N,N-dimethylformamide (DMF) [78,79]. In this method, Fig.…”

Section: Synthesis Of Cannabidiol (Cbd)mentioning

confidence: 99%

A review on the syntheses of Dronabinol and Epidiolex as classical cannabinoids with various biological activities including those against SARS-COV2

Tadayon

Ramazani

2021

J IRAN CHEM SOC

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The very important psychoactive phytocannabinoid from Cannabis Δ 9 tetrahydrocannabinol (Δ 9-THC) and its non-psychotropic member is cannabidiol (CBD). These compounds have a variety of pharmacological activities. THC has been approved for the treatment of nausea caused by chemotherapy, multiple sclerosis and chronic and neuropathic pain and research is underway to use it to treat stimulation of dementia, anorexia nervous and Tourette's syndrome. CBD has therapeutic benefits in Epilepsy, neuroprotective, cancer, inflammatory and anxiety. Recognizing candidate drugs efficiently in the new SARS-CoV2 disease 2019 (Covid-19) is crucial. Cannabidiol and Δ 9-tetrahydrocannabinol have immunomodulatory and anti-inflammatory effects. They can reduce the uncontrolled cytokine production of acute lung injury. Although THD and CBD can be extracted from natural sources due to the disadvantages of this method such as difficulty in purification, cultivation, etc. It has been proven that chemical-synthesis methods of these two compounds can solve these problems. This review briefly summarizes the chemical-synthetic strategies of Dronabinol and Epidiolex from THC and CBD.

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Synthese und Chiralität des (‐)‐Cannabidiols Vorläufige Mitteilung

Cited by 78 publications

References 18 publications

‘Cannabis’ ontologies I: Conceptual issues with Cannabis and cannabinoids terminology

‘Cannabis’ ontologies I: Conceptual issues with Cannabis and cannabinoids terminology

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

A review on the syntheses of Dronabinol and Epidiolex as classical cannabinoids with various biological activities including those against SARS-COV2

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