What molecule am I?
Everyone knows (or should know) that (−)-trans-Δ9-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.
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.
July 9, 2018
Cannabidiol (CBD) is the term for a family of cannabinoids that are isomers of THC, the chief psychoactive component of marijuana. These compounds are not psychoactive, but they are useful for controlling pain and other medical conditions. Up to now, CBD had an unclear regulatory status; but it now has its first approval from the US Food and Drug Administration. On June 25, FDA approved an oral solution of CBD for treating seizures from two severe forms of epilepsy.
April 17, 2023
Cannabidiol1 (CBD) is a non-psychoactive marijuana constituent that is useful for controlling pain and other medical conditions. Perfluorooctanesulfonic acid2 (PFOS) was the Molecule of the Week for January 28, 2019. It was once a widely used surfactant; but because it became an environmental pollutant—even appearing in human blood—it was removed from the market.
What’s the connection between CBD and PFOS? Earlier this month, Hang Yin, Shu Li, and co-workers at Northeast Agricultural University (Harbin, China) reported that administering CBD can attenuate PFOS-induced heart injury. In a mouse study, the researchers found that CBD alleviates myocardial cell apoptosis caused by PFOS by restoring antioxidant capacity, mitochondrial function, and energy metabolic homeostasis to the cells.
1. CAS Reg. No. 13956-29-1.
2. CAS Reg. No. 1763-23-1.
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