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Cannabinol: degradation leads to opportunity?

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Cannabinol: degradation leads to opportunity?

Abdul R Mohammad, Sergio Pagliazzi

Cannabinol (CBN) is the cannabinoid which is generally indicative of the age of the cannabis plant. This is because CBN is formed from the degradation of THC on exposure to heat and UV light, and this conversion occurs over time-subject to storage conditions. As well being a degradation product of THC, it has also shown to be a rapid metabolite of THC in the blood (McCallum et al., 1975).

The-degradation-of-THC-to-CBN
Figure 4: The degradation of THC to CBN, which occurs in the presence of heat and UV light. The reaction is a partial hydrogenation of one of the aromatic rings of THC.

 

CBN acts as a weak agonist to CB1 and CB2, about four times less potent at CB1 compared to THC (Rhee et al., 1997). CBN exhibited a much higher inhibitory constant (Ki) than THC (about 6 times higher) on brain CB1 receptors, indicated in brain synaptosomal binding experiments (Rhee et al., 1997). Hence it has a much lower affinity to CB1 as compared to THC. This could provide the explanation behind CBNs minimal psychoactive effects. CBN is metabolised to 11-OH-CBN (via 11- hydroxylation), which is twice as potent as CBN on CB1 receptors but can only exhibit partial agonist activity at the CB2 receptor (Rhee et al., 1997). Even though it is more potent on brain CB1 receptors than CBN, it is still three times less potent than THC on these receptors (Rhee et al., 1997). It has shown to have less than 10% of the Psychoactive and cardio acceleratory effects of THC in humans (Howlett, 1987). In another study the effects of CBN were considered to be less intense (both physiologically and psychologically) in humans subjects compared with the effects of THC (Hiltunen and Jrbe, 1986).

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