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Greatest Minor Cannabinoid: CBN

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An October 2022 study entitled "Cannabinol: History, Syntheses, and Biological Profile of the Greatest Minor Cannabinoid" that was published in the journal Plants investigated the cannabinoid cannabinol (CBN), calling it a "forgotten and mistreated phytocannabinoid due prominence and attention." The study focused on the "well-known synthetic pathways and highlighted the urgent need to fill the gaps in the biological field."

The researchers explained that early studies about cannabinoids "focused almost exclusively on the narcotic principle of marijuana, ∆9-tetrahydrocannabinol (∆9-THC), eventually expanding to the other related compounds, which are cannabidiol (CBD), cannabigerol (CBG), and cannabichromene (CBC), that together form a group of compounds often referred to as 'the major cannabinoids' or 'big four.'"

Cannabis is capable of producing "more than 150 other compounds referred to as 'minor cannabinoids.'"

The study reported that most research to date has focused on these "big four" cannabinoids "due to their high extraction yield from vegetable sources or easy accessibility through total synthesis." However, it noted that the cannabis botanical species is capable of producing "more than 150 other compounds referred to as 'minor cannabinoids,' which have significant structural differences and specific biological properties."

Reported the study: "CBN was probably considered a 'minor' phytocannabioid owing to its unfortunate and confusing discovery: It was the first phytocannabinoid to be isolated from hashish in the late 19th century, but its structure was not fully solved until 1940 due to some issues related to both nomenclature misunderstandings and the nature of the plant material used for the extraction. This confusing situation—associated with its limited availability and the discovery of more interesting bioactive phytocannabinoids—severely hindered its characterization from a biological and pharmacological standpoint."

CBN molecular structure

Study Conclusions

"The studies reviewed demonstrate the significant contribution that CBN has made to the development of knowledge pertaining, from chemical and biological perspectives, to the field of cannabinoids, even if in a sometimes indirect and particular manner.

"CBN has unfortunately often been overlooked in favor of its analogues which demonstrate a more marked and promising biological profile."

"Since the beginning of the chemistry associated with the study of this class of compounds, CBN has played a crucial role, actively participating in the clarification of their biological properties, the elucidation of the structure of the major cannabinoids, and the development of innovative and efficient extraction and purification processes.

"As a result of the subsequent isolation of the major cannabinoids, particularly CBD and ∆9-THC, and the discovery of the remarkable biological activity associated with them, CBN has unfortunately often been overlooked in favor of its analogues which demonstrate a more marked and promising biological profile; however, it has recently regained prominence following the discovery of the ECS and the multitude of targets that comprise it and provide new avenues for the study and treatment of a broad spectrum of diseases.

"Despite the large number of biological studies conducted on this compound, further research is necessary: extensive data on pharmacokinetics and pharmacodynamics are required, especially on larger mammals, as well as a complete screening on the large number of secondary targets correlated to the ECS.

"The peculiar structure of CBN has made it the target compound...from the 1940s to present day."

"The peculiar biphenyl structure of CBN has made it the target compound for the validation of numerous and diversified synthetic techniques, keeping it in high regard from the 1940s to the present day, and a number of important synthetic methodologies have been developed through the study of its chemistry, including a straightforward one-pot protocol for its synthesis from commercially available source materials.

"The current simplicity of synthesis, both of CBN and its analogues, combined with the largely unknown biological properties, make this class of benzo[c]-chromenic structured compounds one of the most powerful platforms for exploration of the biological space associated with the chemotype of cannabinoids."

View the original study.

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