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Cannabinol
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===Chemical structure=== {{Citations needed|section|date=November 2023}} Cannabinoid receptor agonists are categorized into four groups based on chemical structure. CBN, as one of the many phytocannabinoids derived from ''[[Cannabis sativa|Cannabis Sativa L]]'', is considered a classical cannabinoid. Other examples of compounds in this group include dibenzopyran derivatives such as Δ<sup>9</sup>-THC, well-known for underlying the subjective "high" experienced by cannabis users, as well as Δ<sup>8</sup>-THC, and their synthetic analogs. In contrast, endogenously produced cannabinoids (i.e., endocannabinoids), which also exert effects through CB agonism, are considered [[eicosanoid]]s, distinguished by notable differences in chemical structure. Compared to Δ<sup>9</sup>-THC, one additional aromatic ring confers CBN with a slower and more limited metabolic profile (see {{slink||CBN Formation & Metabolism}}). In contrast to THC, CBN has no [[Cis–trans isomerism|double bond isomers]] nor [[stereoisomer]]s. CBN can degrade into [[HU-345]] from oxidation. In the case of oral administration of CBN, first-pass metabolism in the liver involves the addition of a hydroxyl group at C9 or C11, increasing the affinity and specificity of CBN for both CB1 and CB2 receptors (see [[11-Hydroxycannabinol|11-OH-CBN]]).
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