Elsevier

Life Sciences

Volume 78, Issue 5, 22 December 2005, Pages 539-548
Life Sciences

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Chemical constituents of marijuana: The complex mixture of natural cannabinoids

https://doi.org/10.1016/j.lfs.2005.09.011Get rights and content

Abstract

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.

Section snippets

Chemistry and constituents of Cannabis sativa L.

Marijuana is the crude drug derived from the plant Cannabis sativa L. a plant that is currently accepted as belonging to a family (Cannabaceae) that has only one genus (Cannabis) with only one species (sativa) that is highly variable.

Cannabis has had a long history of use (over 5000 years) starting in Central and Northeast Asia with current use spreading worldwide as a recreational drug or as a medicine albeit unauthorized. Several historic reviews have been written on Cannabis use as a

Cannabinoids: 70 known (4 new)

The typical C21 group of compounds present in C. sativa L. is known as cannabinoids and includes their analogs and transformation products (Razdan, 1987). Five different numbering systems have been used for the cannabinoids (Fig. 1; Eddy, 1965). Compounds in this review will be numbered according to these systems, or if needed, by using the Chemical Abstract Index numbering. The 70 known cannabinoids can be classified as follows:

Other constituents: 419 known (2 new)

The following chemical classes (number known) has been identified in marijuana: nitrogenous compounds (27), amino acids (18), proteins (3), enzymes (6), glycoproteins (2), sugars and related compounds (34), hydrocarbons (50), simple alcohols (7), simple aldehydes (12), simple ketones (13), simple acids (20), fatty acids (23), simple esters (12), lactones (1), steroids (11), terpenes (120), non-cannabinoid phenols (25), flavonoids [23, including 2 new flavonol glycosides, namely kaempferol 3-O

Acknowledgments

The authors acknowledge the support of the National Institute on Drug Abuse for funding much of our work in dealing with the chemistry of the plant over the years.

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