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| CBN | |
|---|---|
| Name | Cannabinol |
| Caption | Structural formula of cannabinol |
| Formula | C21H26O2 |
| Molar mass | 310.43 g·mol−1 |
| Synonyms | CBN |
| Category | Cannabinoid |
CBN
CBN is a minor cannabinoid found in cannabis plant material and in aged cannabis preparations. It is structurally related to other phytocannabinoids and arises predominantly from oxidative degradation processes; historically it was among the first cannabinoids to be isolated and characterized in early 20th‑century natural product chemistry. Interest in CBN spans biochemical studies, pharmacology, forensic chemistry, commercial extraction, and regulatory debates involving public health and intellectual property.
The trivial name derives from historical nomenclature used in natural product studies contemporaneous with the work of Sir Robert Robinson, Thomas H. Morgan-era biochemists, and early 20th‑century pharmacognosy texts. Abbreviations used in analytical chemistry and regulatory filings follow the International Union of Pure and Applied Chemistry conventions similar to abbreviations used for THC, CBD, and CBG in publications from institutions such as the National Institutes of Health, Food and Drug Administration, and national forensic laboratories. Systematic names follow IUPAC rules and are used in databases maintained by bodies like the Chemical Abstracts Service and PubChem.
CBN is a bicyclic dibenzopyran derivative with the molecular formula C21H26O2; its structure resembles oxidative aromatization products of Δ9-tetrahydrocannabinol derivatives reported in analytical chemistry literature. Pharmacologically, CBN exhibits affinity for cannabinoid receptor subtypes such as CB1 receptor and CB2 receptor with lower potency compared to Δ9-THC; receptor binding and functional assays by researchers at institutions like Columbia University, University of Mississippi, and Johns Hopkins University indicate partial agonist or weak agonist activity in vitro. CBN also interacts with non-cannabinoid targets including transient receptor potential channels characterized in studies from labs affiliated with Harvard University and Massachusetts Institute of Technology. Metabolic pathways in mammalian systems involve hepatic cytochrome P450 enzymes, as described in pharmacokinetic investigations from University College London and the University of California, San Francisco.
Isolation techniques for CBN employ chromatographic separation methods such as preparative high‑performance liquid chromatography used by analytical groups at Agilent Technologies and Shimadzu-equipped laboratories. Classical extraction from botanical material uses solvent partitions adapted from protocols at Charles University and botanical chemistry groups at University of Oxford; aged resin and heat‑treated samples yield higher CBN content through oxidative conversion of THC precursors, a transformation monitored in studies linked to Royal Society of Chemistry publications. Total synthesis routes and semi‑synthetic oxidations have been reported by research groups at Stanford University, ETH Zurich, and corporate chemistry teams at Pfizer and Eli Lilly, employing reagents common to organic synthesis such as DDQ and other oxidants.
Clinical interest in CBN has focused on potential sedative, analgesic, and anti‑inflammatory properties investigated in preclinical models at institutions including Stanford University School of Medicine, Mayo Clinic, and Cleveland Clinic. Small animal studies and in vitro assays from laboratories at University of Toronto and Monash University suggest synergistic interactions with CBD and THC in modulating nociception and inflammation. Human clinical trials remain limited compared with trials for agents studied at National Institutes of Health‑funded centers; ongoing pilot studies at academic medical centers such as University of California, Los Angeles and Imperial College London examine sleep and pain outcomes.
Toxicological evaluations reference preclinical safety data generated at contract research organizations and academic toxicology units associated with Boston University and Yale School of Medicine. Reported adverse effects in animal models include doses‑dependent alterations in locomotor activity and sedation; comparative assessments reference safety profiles of THC and CBD evaluated by regulatory agencies such as the European Medicines Agency and Food and Drug Administration. Drug interaction concerns involve cytochrome P450 inhibition or induction pathways characterized by pharmacologists at Karolinska Institutet and Uppsala University.
Regulatory classification of CBN varies: in some jurisdictions it is treated under statutes that govern cannabinoid derivatives enforced by agencies like the Drug Enforcement Administration in the United States, while other countries apply frameworks administered by ministries such as the Home Office in the United Kingdom or the Ministry of Health, Brazil. Legal determinations often reference scheduling decisions for THC and interpretation of analogue laws adjudicated in courts including Supreme Court of the United States and national appellate courts. Product labeling, advertising, and interstate commerce implications are addressed in regulatory guidance from agencies including the Federal Trade Commission and national customs authorities.
The nutraceutical and wellness market includes CBN‑containing products marketed by companies such as multinational retailers and specialized firms reviewed in analyses by Deloitte, McKinsey & Company, and Euromonitor International. Product forms include tinctures, topicals, and inhalable formulations produced by manufacturers utilizing extraction technologies supplied by firms like Corteva and analytical testing by laboratories accredited by American Association for Laboratory Accreditation. Branding, supply chain considerations, and patent activity engage intellectual property practices overseen by bodies such as the United States Patent and Trademark Office and the European Patent Office.
Controversies concern evidence gaps highlighted in systematic reviews published in journals associated with Nature Publishing Group, Elsevier, and Springer Nature, as well as debates over marketing claims litigated in courts such as the United States District Court and consumer protection actions involving agencies like the Federal Trade Commission. Research priorities promoted by funding agencies including National Science Foundation, Medical Research Council (UK), and Canadian Institutes of Health Research emphasize rigorous randomized controlled trials and standardized analytical methods developed in interlaboratory studies coordinated by organizations like the International Organization for Standardization and American Chemical Society.
Category:Cannabinoids