|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||310.437 g·mol−1|
|3D model (JSmol)|
|Melting point||77 °C (171 °F) |
|Solubility in water||insoluble in water soluble in methanol and ethanol mg/mL (20 °C)|
|(what is this?)|
Cannabinol (CBN) is a mildly psychoactive cannabinoid that binds to the cannabinoid receptors with more selectivity for CB2 over CB1 found in trace amounts from Cannabis. CBN is mostly found in cannabis that is aged and stored, and is derived from the plant's main psychoactive chemical, tetrahydrocannabinol (THC).
It was the first cannabis compound to be isolated from cannabis extract in the late 1800s. Its structure and chemical synthesis were achieved by 1940.
Delta-9-THC can degrade into CBN from oxidation.
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. Both THC and CBN activate the CB1 (Ki = 211.2 nM) and CB2 (Ki = 126.4 nM) receptors. It is metabolised to 11-OH-CBN, which is a more potent CB1 agonist than CBN but acts as a weak antagonist at CB2.
In contrast to THC, CBN has no double bond isomers nor stereoisomers.
CBN can degrade into HU-345 from oxidation.
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.
According to the 2018 Farm Bill, extracts from the Cannabis sativa L. plant, including CBN, are legal under US federal law as long as they have a delta-9 Tetrahydrocannabinol (THC) concentration of 0.3 percent or less. However, as of 2022 in the United States, CBN and other cannabis extracts remain illegal under federal law to prescribe for medical use or to use as an ingredient in dietary supplements or other foods, and sales or possession of CBN could potentially be prosecuted 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.
Cannabinol (CBN; Figure 1), much of which is thought to be formed from THC during the storage of harvested cannabis, was the first of the plant cannabinoids (phytocannabinoids) to be isolated, from a red oil extract of cannabis, at the end of the 19th century. Its structure was elucidated in the early 1930s by R.S. Cahn, and its chemical synthesis first achieved in 1940 in the laboratories of R. Adams in the U.S.A. and Lord Todd in the U.K.
Cannabinol (CBN) is the nonenzymatic oxidation byproduct of THC and is most commonly an artifact found after prolonged storage, especially at higher temperatures. CBN was the first cannabinoid to be identified and isolated from cannabis (Wood, Spivey, & Easterfield, 1899)