Cannabinol (CBN)

Overview

• Type: Mildly psychoactive phytocannabinoid
• Mechanism: Low affinity partial agonist at CB1 & CB2 receptors
• Discovery: First isolated from cannabis in 1896
• Legal Status:
  • CA: Unscheduled
  • UK: Class B
  • US: Unscheduled

Chemical and Physical Data

• Formula: C21H26O2
• Molar Mass: 310.437 g/mol
• Melting Point: 76-77°C (169-171°F)
• Solubility:
  • Insoluble in water
  • Soluble in methanol and ethanol

Pharmacology

Pharmacodynamics

• Activates CB1 (Ki = 211.2 nM) and CB2 (Ki = 126.4 nM) receptors
• Lower affinity compared to THC
• Higher selectivity for CB2 receptors, primarily associated with immune function
• Demonstrates antimicrobial effects, especially with antibiotic-resistant bacteria
• Acts as ANKTM1 channel agonist at high concentrations (>20 nM)
• Limited evidence of interaction with nociceptive and immune-related signaling via TRP channels
• Preclinical studies suggest inhibitory effects on GI motility

Entourage Effect

• Describes synergistic effect of cannabinoids when combined with other cannabis compounds (e.g., flavonoids, terpenoids)

Potential Therapeutic Properties

• Antimicrobial and Anti-inflammatory effects
• Potential Efficacy:
  • Ocular disease
  • Epidermolysis bullosa
  • Synergistic neuroprotective effects with other cannabinoids

Biosynthesis

• Unique in that it is generated through oxidation of THC, not from a pre-existing acidic form
• Found in trace amounts in aged and stored cannabis

Pharmacokinetics

• Administered orally or via inhalation
• Bioavailability is low due to high lipophilicity & first-pass metabolism
• Metabolized by CYP450 isoforms 2C9 & 3A4
• Primary active metabolite: 11-OH-CBN
• Inhalation bioavailability ~40% that of intravenous
• Half-life is variable, affected by genetic factors

Chemistry

• Considered a classical cannabinoid
• Compared to THC, CBN has an additional aromatic ring

History

• Isolated in late 1800s
• Structure identified by Cahn in the early 1930s
• Structure and synthesis achieved by 1940
• Early research focused on effects of individual cannabis-derived compounds

Legal and Regulatory Context

• Not listed in UN's international drug control treaties
• Legal in the US under the 2018 Farm Bill if THC concentration is 0.3% or less

References

• Cited various studies and articles for pharmacological and chemical data

Related Research Areas

• Neurotransmitter interactions
• Cannabinoid receptor agonism and its effects on brain synaptic plasticity

These notes provide a concise summary of CBN, its pharmacological properties, potential therapeutic uses, and legal status. Further details can be explored through referenced studies and articles provided in the Wikipedia article.