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Review
. 2021 May 8;26(9):2774.
doi: 10.3390/molecules26092774.

Cannabinoids, Phenolics, Terpenes and Alkaloids of Cannabis

Mohamed M Radwan  1 , Suman Chandra  1 , Shahbaz Gul  2   3 , Mahmoud A ElSohly  1   3   4
Affiliations
Review

Cannabinoids, Phenolics, Terpenes and Alkaloids of Cannabis

Mohamed M Radwan et al. Molecules. .

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 C21 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.

Keywords: Cannabis sativa; alkaloids; cannabinoids; flavonoids; non-cannabinoid phenols; terpenes.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Δ9-THC-Type Cannabinoids.
Figure 2
Figure 2
Δ8-THC-Type Cannabinoids.
Figure 3
Figure 3
CBG-Type Cannabinoids.
Figure 4
Figure 4
CBD, CBND, CBE and CBL-Type Cannabinoids.
Figure 5
Figure 5
CBC and CBN-Type Cannabinoids.
Figure 6
Figure 6
CBT-Type Cannabinoids.
Figure 7
Figure 7
Miscellaneous-Type Cannabinoids.
Figure 8
Figure 8
Miscellaneous-Type Cannabinoids (cont.).
Figure 9
Figure 9
Chemical structure of Cannabis Spiro-Indans.
Figure 10
Figure 10
Chemical structure of Cannabis dihydrostilbenes.
Figure 11
Figure 11
Chemical structure of Cannabis Dihydrophenanthrene Derivatives.
Figure 12
Figure 12
Chemical Structures of Cannabis Simple Phenols.
Figure 13
Figure 13
Chemical Structures of Cannabis Flavonoids.
Figure 14
Figure 14
Chemical Structure of Cannabis Monoterpenes (hydrocarbon derivatives).
Figure 15
Figure 15
Chemical Structure of Cannabis Oxygenated Monoterpenes (acyclic, monocyclic and bicyclic).
Figure 16
Figure 16
Chemical Structures of Cannabis Sesquiterpenes.
Figure 17
Figure 17
Chemical Structures of Cannabis Diterpenes, Triterpenes, and Miscellaneous Terpenes.
Figure 18
Figure 18
Chemical structure of Cannabis Alkaloids.
See this image and copyright information in PMC

References

    1. Zuardi A.W. History of cannabis as a medicine: A review. Braz. J. Psychiatry. 2006;28:153–157. doi: 10.1590/S1516-44462006000200015. - DOI - PubMed
    1. ElSohly M.A., Slade D. Chemical constituents of marijuana: The complex mixture of natural cannabinoids. Life Sci. 2005;78:539–548. doi: 10.1016/j.lfs.2005.09.011. - DOI - PubMed
    1. Turner C.E., Elsohly M.A., Boeren E.G. Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J. Nat. Prod. 1980;43:169–234. doi: 10.1021/np50008a001. - DOI - PubMed
    1. Mechoulam R., Carlini E.A. Toward drugs derived from cannabis. Naturwissenschaften. 1978;65:174–179. doi: 10.1007/BF00450585. - DOI - PubMed
    1. Cunha J.M., Carlini E., Pereira A.E., Ramos O.L., Pimentel C., Gagliardi R., Sanvito W., Lander N., Mechoulam R. Chronic administration of cannabidiol to healthy volunteers and epileptic patients. Pharmacology. 1980;21:175–185. doi: 10.1159/000137430. - DOI - PubMed

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