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112 Recent Patents on CNS Drug Discovery, 2009, 4, 112-136
Naturally Occurring and Related Synthetic Cannabinoids and their Potential Therapeutic Applications
Ahmed M. Galal1,*, Desmond Slade1, Waseem Gul1,5, Abir T. El-Alfy2, Daneel Ferreira1,3 and Mahmoud A. Elsohly1,4,5
1National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, 2Department of Pharmacology, School of Pharmacy, The University of Mississippi, University, MS 38677, 3Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677, 4Department of Pharmaceutics, School of Pharmacy, The University of Mississippi, University, MS 38677, and 5ElSohly Laboratories, Inc., 5 Industrial Park Drive, Oxford, MS 38655
Received: October 9, 2008; Accepted: November 3, 2008; Revised: November 17, 2008
Abstract: Naturally occurring cannabinoids (phytocannabinoids) are biosynthetically related terpenophenolic compounds uniquely produced by the highly variable plant, Cannabis sativa L. Natural and synthetic cannabinoids have been extensively studied since the discovery that the psychotropic effects of cannabis are mainly due to !9-THC. However, cannabinoids exert pharmacological actions on other biological systems such as the cardiovascular, immune and endocrine systems. Most of these effects have been attributed to the ability of these compounds to interact with the cannabinoid CB1 and CB2 receptors. The FDA approval of Marinol®, a product containing synthetic "9-THC (dronabinol), in 1985 for the control of nausea and vomiting in cancer patients receiving chemotherapy, and in 1992 as an appetite stimulant for AIDS patients, has further intensified the research interest in these compounds. This article reviews patents (2003-2007) that describe methods for isolation of cannabinoids from cannabis, chemical and chromatographic methods for their purification, synthesis, and potential therapeutic applications of these compounds.
Keywords: Cannabis sativa L, cannabinoids, phytocannabinoids, pharmacological actions, CB1 and CB2 receptors, isolation, purification, synthesis, therapeutic applications.
Cannabinoids are terpenophenolic secondary plant metabolites uniquely found in Cannabis sativa L. . Biogenetically they are derived from a mixed origin, with the 3-alkylphenol moiety originating from a polyketide pre- cursor and the tetrahydroisochroman moiety from a mono- terpene residue . Cannabinoids found in cannabis are designated as phytocannabinoids or exogenous cannabinoids to distinguish them from the eicosanoid endocannabinoids, a group of arachidonoyl esters and amides that were first discovered in 1988 in mammalian tissues acting as endo- genous cannabinoid receptor ligands with neuromodulatory action .
Cannabis is divided mainly into three phenotypes or chemotypes: Phenotype I (drug type), with (-)-trans-(6aR, 10aR)-!9-tetrahydrocannabinol (!9-THC) (1) > 0.3% and cannabidiol (CBD) (2) < 0.5%; an intermediate phenotype II (intermediate type), with (2) as the major cannabinoid but with (1) also present at various concentrations; and phenotype III (fiber type), with especially low (1) content. The rare phenotypes IV and V have low (1) and (2) content and high cannabigerol (CBG) (3) content, and undetectable amounts of any cannabinoid, respectively (Table 1) . All analyses are based on plant inflorescence dry material. Although environmental factors play a role in the amount of cannabinoids present in different parts of the plant at
*Address correspondence to this author at the National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA; Tel: +1-662-915-5928;
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different growth stages , the tripartite distribution of (2):(1) ratios in most populations (phenotypes I to III) are under genetic control [4c].
Not only is the isolation and purification of cannabinoids challenging owing to the structural, physical and chemical similarity of these compounds, but synthetic routes are equally demanding due to low yields and the formation of by-products while the final products are typically non- crystalline. The critical step in the majority of synthesis routes yielding (1) [in cannabinoid parlance, synthetic (1) is called dronabinol] is the condensation of a monoterpene with a resorcinol derivative such as olivetol (5-pentyl-1,3- benzenediol). Presently, condensation of (+)-p-mentha-2,8- dien-1-ol with olivetol is used to produce commercial (1). In addition, the thermodynamic instability of (1) must always be considered during isolation, synthesis and storage, since
© 2009 Bentham Science Publishers Ltd.
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