Cannabinol (CAS 521-35-7) is a mildly psychoactive cannabinoid formed primarily through the oxidative degradation of tetrahydrocannabinol (THC), often accumulating in aged cannabis material. It exhibits a unique pharmacological profile characterized by a higher affinity for CB2 receptors than CB1, contributing to its potential therapeutic applications in sleep regulation, pain relief, and as an anti-inflammatory agent. While its psychoactive effects are significantly weaker than THC, its role as a marker for cannabis aging and its emerging bioactivity make it a compound of growing interest in medicinal and analytical research.
Name :
CannabinolCAS No. :
521-35-7MF :
C₂₁H₂₆O₂MW :
310.43Purity :
98%Appearance :
Thin platelets or crystalline solidStorage Condition :
Soluble in ethanol, ether, benzene, and alkaline solutionsChemial Properties
Chemical Name:Cannabinol
Synonym:CBN
CAS Number: 521-35-7
Molecular Formula: C₂₁H₂₆O₂
Molecular Weight: 310.43 g/mol
Appearance: Thin platelets or crystalline solid
Melting Point: 76–77°C
Boiling Point: 185°C (sublimes under vacuum)
Density: 1.0865 g/cm³ (estimated)
Solubility:
Insoluble in water
Soluble in ethanol, ether, benzene, and alkaline solutions
pKa: 9.40 ± 0.40 (predicted)
SMILES Notation: C1(O)=CC(CCCCC)=CC(O)=C1C/C=C(\C)/CC/C=C(\C)\C
InChI: InChI=1S/C21H26O2/c1-5-6-7-11-18-14-20(22)19(21(23)15-18)13-12-17(4)10-8-9-16(2)3/h9,12,14-15,22-23H,5-8,10-11,13H2,1-2H3
Biological and Pharmacological Roles
CBN is a non-psychoactive cannabinoid derived from the oxidation of THC. Key roles include:
Sedative: Enhances sleep quality by modulating GABA receptors and slowing adenosine reuptake .
Analgesic: Reduces neuropathic pain via TRPV2 channel modulation .
Anti-Inflammatory: Suppresses COX-2 and TNF-α activity in immune cells .
Neuroprotective: Protects retinal ganglion cells and reduces intraocular pressure in glaucoma models .
Appetite Stimulation: Activates CB₁ receptors to increase food intake in animal studies .
Mechanism of Action
Receptor Interaction: Weak partial agonist at CB₁ (Ki = 126 nM) and CB₂ (Ki = 211 nM) receptors .
Ion Channel Modulation: Slows sodium channel inactivation, reducing neuronal excitability .
Enzyme Modulation: Inhibits FAAH, enhancing anandamide signaling .
Medical Applications
Synthesis and Production
Natural Extraction: Isolated from aged cannabis (THC oxidation product).
Chemical Synthesis:
Oxidation of THC: Exposure to heat/light converts THC to CBN.
Iodine-Mediated Synthesis: One-pot reaction using olivetol and terpenoids.
FAQ
Q: Can you explain the entourage effect between CBN and other cannabinoids?
A: The synergistic effects of CBN with CBD and THC are achieved through receptor complementation, metabolic regulation, and terpene enhancement, particularly prominent in sleep, pain relief, and mood management. Although further research is needed, existing evidence supports the clinical application value of full-spectrum or broad-spectrum products (containing specific ratios of cannabinoids and terpenes).
Q: What are the most recent clinical trials involving CBN for sleep disorders?
A: Recent trials underscore CBN’s potential as a non-intoxicating sleep aid, particularly through metabolite-driven mechanisms. While single-dose efficacy is clear, long-term studies (2025–2026) will clarify its role in chronic insomnia and comorbid conditions like anxiety.
Q: How does CBN compare to other sleep aids like melatonin in terms of efficacy and side effects?
A: For Immediate Relief: Melatonin is better supported for short-term sleep onset issues.
For Sleep Quality: CBN may offer subtle benefits for maintaining sleep but lacks robust evidence.
Safety: Melatonin has more documented side effects, while CBN’s profile is gentler but understudied.
Recommendation: Prioritize melatonin for circadian adjustments and CBN for anxiety-driven insomnia, but consult a healthcare provider for chronic sleep disorders.
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