Cannabinol

Cannabinol

Clinical data
ATC code	none
Legal status
Legal status	CA: Schedule II UK: Class B
Identifiers
IUPAC name 6,6,9-Trimethyl-3-pentyl-benzo[c]chromen-1-ol
CAS Number	521-35-7 N
PubChem (CID)	2543
IUPHAR/BPS	740
ChemSpider	2447 Y
UNII	7UYP6MC9GH Y
KEGG	C07580 Y
ChEMBL	CHEMBL74415 Y
ECHA InfoCard	100.216.772
Chemical and physical data
Formula	C21H26O2
Molar mass	310.4319 g/mol
3D model (Jmol)	Interactive image
Melting point	77 °C (171 °F)
Solubility in water	insoluble in water soluble in methanol and ethanol mg/mL (20 °C)
SMILES Oc2cc(cc1OC(c3c(c12)cc(cc3)C)(C)C)CCCCC
InChI InChI=1S/C21H26O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9-13,22H,5-8H2,1-4H3 Y Key:VBGLYOIFKLUMQG-UHFFFAOYSA-N Y
NY (what is this?)

insoluble in water

Cannabinol (CBN) is a weak psychoactive cannabinoid found only in trace amounts in Cannabis sativa and Cannabis indica. Pharmacologically relevant quantities are formed as a metabolite of tetrahydrocannabinol (THC) . CBN acts as a partial agonist at the CB₁ receptors, but has a higher affinity to CB₂ receptors, however; with lower affinities in comparison to THC. Degraded or oxidized cannabis products, such as low-quality baled cannabis and traditionally produced hashish, are high in CBN, but modern production processes minimize the formation of CBN. Cannabinol has been shown to have analgesic properties.

Unlike other cannabinoids, CBN does not stem from cannabigerol (CBG) but rather is the degraded product of THC. If cannabis is exposed to air or ultraviolet light (for example, in sunlight) for a prolonged period of time, tetrahydrocannabinolic acid (THCA) will convert to cannabinolic acid (CBNA). CBN is then formed by decarboxylation of CBNA.

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

CBN is not scheduled by the United Nations' Convention on Psychotropic Substances.