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      Cannabinoids, Phenolics, Terpenes and Alkaloids of Cannabis

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          Abstract

          Cannabis sativa is one of the oldest medicinal plants in the world. It was introduced into western medicine during the early 19th century. It contains a complex mixture of secondary metabolites, including cannabinoids and non-cannabinoid-type constituents. More than 500 compounds have been reported from C. sativa, of which 125 cannabinoids have been isolated and/or identified as cannabinoids. Cannabinoids are C 21 terpeno-phenolic compounds specific to Cannabis. The non-cannabinoid constituents include: non-cannabinoid phenols, flavonoids, terpenes, alkaloids and others. This review discusses the chemistry of the cannabinoids and major non-cannabinoid constituents (terpenes, non-cannabinoid phenolics, and alkaloids) with special emphasis on their chemical structures, methods of isolation, and identification.

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          Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects.

          Ethan Russo (2011)
          Tetrahydrocannabinol (THC) has been the primary focus of cannabis research since 1964, when Raphael Mechoulam isolated and synthesized it. More recently, the synergistic contributions of cannabidiol to cannabis pharmacology and analgesia have been scientifically demonstrated. Other phytocannabinoids, including tetrahydrocannabivarin, cannabigerol and cannabichromene, exert additional effects of therapeutic interest. Innovative conventional plant breeding has yielded cannabis chemotypes expressing high titres of each component for future study. This review will explore another echelon of phytotherapeutic agents, the cannabis terpenoids: limonene, myrcene, α-pinene, linalool, β-caryophyllene, caryophyllene oxide, nerolidol and phytol. Terpenoids share a precursor with phytocannabinoids, and are all flavour and fragrance components common to human diets that have been designated Generally Recognized as Safe by the US Food and Drug Administration and other regulatory agencies. Terpenoids are quite potent, and affect animal and even human behaviour when inhaled from ambient air at serum levels in the single digits ng·mL(-1) . They display unique therapeutic effects that may contribute meaningfully to the entourage effects of cannabis-based medicinal extracts. Particular focus will be placed on phytocannabinoid-terpenoid interactions that could produce synergy with respect to treatment of pain, inflammation, depression, anxiety, addiction, epilepsy, cancer, fungal and bacterial infections (including methicillin-resistant Staphylococcus aureus). Scientific evidence is presented for non-cannabinoid plant components as putative antidotes to intoxicating effects of THC that could increase its therapeutic index. Methods for investigating entourage effects in future experiments will be proposed. Phytocannabinoid-terpenoid synergy, if proven, increases the likelihood that an extensive pipeline of new therapeutic products is possible from this venerable plant. http://dx.doi.org/10.1111/bph.2011.163.issue-7. © 2011 The Author. British Journal of Pharmacology © 2011 The British Pharmacological Society.
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            Isolation, Structure, and Partial Synthesis of an Active Constituent of Hashish

            Y GAONI, R Mechoulam (1964)
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              Chemical constituents of marijuana: the complex mixture of natural cannabinoids.

              Mahmoud ElSohly, Desmond Slade (2005)
              The cannabis plant (Cannabis sativa L.) and products thereof (such as marijuana, hashish and hash oil) have a long history of use both as a medicinal agent and intoxicant. Over the last few years there have been an active debate regarding the medicinal aspects of cannabis. Currently cannabis products are classified as Schedule I drugs under the Drug Enforcement Administration (DEA) Controlled Substances act, which means that the drug is only available for human use as an investigational drug. In addition to the social aspects of the use of the drug and its abuse potential, the issue of approving it as a medicine is further complicated by the complexity of the chemical make up of the plant. This manuscript discusses the chemical constituents of the plant with particular emphasis on the cannabinoids as the class of compounds responsible for the drug's psychological properties.
              Article 0 comments Cited 281 times – based on 0 reviews     Review now
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                Author and article information

                Contributors
                İhsan Çalış: Role: Academic Editor
                Horváth Györgyi: Role: Academic Editor
                Agnieszka Ludwiczuk: Role: Academic Editor
                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 08 May 2021
                Publication date Collection: May 2021
                Volume: 26
                Issue: 9
                Electronic Location Identifier: 2774
                Affiliations
                [1 ]National Center for Natural Products Research, School of Pharmacy, University of Mississippi, Oxford, MS 38677, USA; mradwan@ 123456olemiss.edu (M.M.R.); suman@ 123456olemiss.edu (S.C.)
                [2 ]ElSohly Laboratories, Inc., 5 Industrial Park Drive, Oxford, MS 38655, USA; swgul@ 123456go.olemiss.edu
                [3 ]Sally McDonnell Barksdale Honors College, University of Mississippi, Oxford, MS 38677, USA
                [4 ]Department of Pharmaceutics and Drug Delivery, School of Pharmacy, University of Mississippi, Oxford, MS 38677, USA
                Author notes
                [* ]Correspondence: melsohly@ 123456olemiss.edu ; Tel.: +1-662-915-5928; Fax: +1-662-915-5587
                Article
                Publisher ID: molecules-26-02774
                DOI: 10.3390/molecules26092774
                PMC ID: 8125862
                PubMed ID: 34066753
                SO-VID: 94046d5c-b5be-4981-9687-082dbf559d3b
                Copyright © © 2021 by the authors.
                License:

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( https://creativecommons.org/licenses/by/4.0/).

                History
                Date received : 22 March 2021
                Date accepted : 04 May 2021
                Categories
                Subject: Review

                Keywords: cannabis sativa,cannabinoids,non-cannabinoid phenols,flavonoids,terpenes,alkaloids
                Data availability:
                Keywords: cannabis sativa, cannabinoids, non-cannabinoid phenols, flavonoids, terpenes, alkaloids

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