Cannabidiol

February 06, 2017
I’m a THC isomer that won’t get you high.
What molecule am I?

Everyone knows (or should know) that (−)-trans9-tetrahydrocannabinol (THC) and many of its cannabinoid isomers are the chief psychoactive components of marijuana (Cannabis sativa). But some THC isomers are not psychoactive and may have some beneficial uses.

Members of the cannabidiol family fall into this category. The structure shown is the one typically used for cannabidiol; it goes by many names, including (–)-cannabidiol, Δ1(2)-trans-cannabidiol, and cannabidiol (7CI). There are at least seven known cannabidiol isomers.

In 1940, the iconic organic chemist Roger Adams and colleagues isolated cannabidiol as its bis(3,5-dinitrobenzoate) ester from C. sativa, which they called “Minnesota wild hemp”. At the time, cannabidiol’s isomerism was not recognized. It was not until the 1960s that its isomers’ absolute configurations were determined and some of them were synthesized.

Israeli scientists led by Raphael Mechoulam discovered in 1970 that cannabidiol and most other cannabinoids are not psychoactive. Since then, cannabidiol has been investigated for medical uses, including treatment for a virulent form of epilepsy. It is a component of some dietary supplements and cosmetics. Biologists are working on developing marijuana strains that suppress THC content and enhance the production of cannabidiol.

Cannabidiol’s regulatory status varies from one jurisdiction to another. The regulations are so irregular that in 2016 the European Industrial Hemp Association issued a position paper that suggested a regulatory protocol with the objective that all European Union countries would operate under the same rules.

MOTW Update

The cyclopentazole anion was the Molecule of the Week for December 12, 2016. Its sodium salt was the first stable N5compound ever synthesized. But this salt is stable only in aqueous solution. More recently, Chong Zhang, Chengguo Sun, and coauthors in China prepared a stable (but complex) crystalline cyclopentazolate salt: (N5)6(H3O)3(NH4)4Cl.

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