Cannabinol [CBN]

Chemical Structure and Synthesis

• Cannabinol (CBN) is a classical cannabinoid derived from Cannabis Sativa L.
• CBN has a slower metabolic profile compared to Δ-THC due to an additional aromatic ring.
• CBN lacks double bond isomers or stereoisomers and can degrade into HU-345 from oxidation.
• CBN is unique as it is generated through the oxidation of THC rather than from an acidic precursor form.
• CBN forms through exposure to heat, oxygen, and/or light in aged cannabis.
• Oral administration of CBN involves first-pass metabolism in the liver, enhancing its affinity for CB1 and CB2 receptors.

Pharmacology and Pharmacokinetics

• CBN activates CB1 and CB2 receptors as a low affinity partial agonist.
• CBN has equivalent or higher affinity to CB2 receptors compared to THC.
• CBN metabolism is mediated by CYP450 isoforms and UGTs, with inhalation having higher bioavailability than oral administration.
• Study of 6 cannabis users found highly variable half-life of 32±17 hours with intravenous administration.
• CBN is metabolized by CYP2C9 and CYP3A4 liver enzymes, sensitivity to genetic factors.
• Genetic factors affect levels of liver enzymes.
• Metabolism similar to CBD.

Entourage Effect and Therapeutic Potential

• The entourage effect describes synergistic effects of cannabinoids and other compounds in cannabis when coadministered.
• Whole-plant-derived cannabis therapeutics may be more effective due to the entourage effect.
• Limited evidence suggests CBN interacts with nociceptive and immune-related signaling via TRP channels.
• CBN, anandamide, and other CB1 agonists have shown inhibitory effects on GI motility in preclinical studies.
• CBN demonstrates antimicrobial effects, especially against antibiotic-resistant bacteria.

Legal Status and Legislation

• CBN not listed in schedules by United Nations Single Convention on Narcotic Drugs.
• Legal under US federal law if THC concentration of 0.3% or less.
• Sales or possession could be prosecuted under Federal Analogue Act.
• Legal status varies internationally.
• 2018 Farm Bill legalized extracts from Cannabis sativa L. with THC concentration of 0.3% or less.
• Legal landscape evolving.

Research and References

• Various studies on cannabinol and its effects.
• Research on therapeutic potential of cannabis and cannabinoids.
• Studies on pharmacology and medicinal properties of cannabinoids.
• Investigations into endocannabinoid system for therapeutic strategies.
• Research on cannabis chemistry, extraction, and therapeutic applications.

Cannabinol Data Sources