Cannabinol


Cannabinol is a mildly psychoactive cannabinoid found only in trace amounts in Cannabis, and is mostly found in aged Cannabis. Pharmacologically relevant quantities are formed as a metabolite of tetrahydrocannabinol. CBN acts as a partial agonist at the CB1 receptors, but has a higher affinity to CB2 receptors; however, it has lower affinities relative to THC. Degraded or oxidized cannabis products, such as low-quality baled cannabis and traditionally produced hashish, are high in CBN.
Unlike other cannabinoids, CBN does not stem directly from cannabigerol or cannabigerolic acid, but rather is the degraded product of tetrahydrocannabinolic acid. If cannabis is exposed to air or ultraviolet light for a prolonged period of time, THCA will convert to cannabinolic acid. CBN is then formed by decarboxylation of CBNA.

Chemistry

In contrast to THC, CBN has no double bond isomers nor stereoisomers. Both THC and CBN activate the CB1 and CB2 receptors.

Legal status

CBN is not listed in the schedules set out by the United Nations' Single Convention on Narcotic Drugs from 1961 nor their Convention on Psychotropic Substances from 1971, so the signatory countries to these international drug control treaties are not required by these treaties to control CBN.

United States

In the United States, federal and state laws regarding the legality of cannabis products are confusing and at times contradictory. CBN is not listed in the list of scheduled controlled substances in the U.S. However, it is possible that CBN could legally be considered an analog of THC or CBD, both of which are Schedule I substances, and therefore sales or possession could potentially be prosecuted under the Federal Analogue Act. It is also possible that CBN may not meet the legal standard of an analogue for the purposes of bringing forth a prosecution under the Federal Analogue Act. In December 2016, the Drug Enforcement Administration added marijuana extracts, which are defined as any "extract containing one or more cannabinoids that has been derived from any plant of the genus Cannabis, other than the separated resin", to Schedule I. This action has led to additional uncertainty about the legal status.