Cannabinol

Title: Cannabinol
CAS Registry Number: 521-35-7
CAS Name: 6,6,9-Trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol
Additional Names: 3-amyl-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran; CBN
Molecular Formula: C21H26O2
Molecular Weight: 310.43
Percent Composition: C 81.25%, H 8.44%, O 10.31%
Literature References: Nonpsychoactive constituent of cannabis, q.v. (Cannabis sativa L. Cannabinaceae); weak cannabinoid receptor ligand. Isoln from cannabis resin: T. B. Wood et al., J. Chem. Soc. 69, 539 (1896); R. S. Cahn, J. Chem. Soc. 1931, 630; T. S. Work et al., Biochem. J. 33, 123 (1939). Structural studies: R. S. Cahn, J. Chem. Soc. 1932, 1342; 1933, 1400; F. Bergel, K. Vögele, Ann. 493, 250 (1932). Structure and synthesis: R. Adams et al., J. Am. Chem. Soc. 62, 2204 (1940). Crystal structure: T. Ottersen et al., Acta Chem. Scand. B 31, 781 (1977). Improved syntheses: P. C. Meltzer et al., Synthesis 1981, 985; J. Novák, C. A. Salemink, Tetrahedron Lett. 23, 253 (1982). Pharmacology: I. Yamamoto et al., Chem. Pharm. Bull. 35, 2144 (1987); F. Petitet et al., Life Sci. 63, 1 (1998). Review of chromatographic determn methods in biological samples: C. Staub, J. Chromatogr. B 733, 119-126 (1999). Comparison of pharmacology with other cannabinoids: I. Yamamoto et al., J. Toxicol. Toxin Rev. 22, 577-589 (2003).
Properties: Leaflets from petr ether, mp 76-77°. Sublimes at 4 mm with a bath temp of 180-190°. bp0.05 185°. Insol in water. Sol in methanol, ethanol, aq alkaline solns.
Melting point: mp 76-77°
Boiling point: bp0.05 185°
Cantharidin Capobenic Acid Capravirine Caprenin Capreomycin

Cannabinol
Cannabinol.svg
Cannabinol 3D.png
Systematic (IUPAC) name
6,6,9-trimethyl-3-pentyl-benzo[c]chromen-1-ol
Clinical data
Legal status  ?
Identifiers
CAS number 521-35-7 N
ATC code None
PubChem CID 2543
IUPHAR ligand 740
ChemSpider 2447 YesY
UNII 7UYP6MC9GH YesY
KEGG C07580 YesY
ChEMBL CHEMBL74415 YesY
Chemical data
Formula C21H26O2 
Mol. mass 310.4319 g/mol
Physical data
Melt. point 77 °C (171 °F) [4]
Solubility in water insoluble in water[1]

soluble in methanol[2] and ethanol[3] mg/mL (20 °C)

 N (what is this?)  (verify)

Cannabinol (CBN) is a weak psychoactive cannabinoid found only in trace amounts in Cannabis sativa and Cannabis indica.[5] It is mostly a metabolite of tetrahydrocannabinol (THC).[6] CBN acts as a weak agonist of CB1 receptors but has a higher affinity to CB2 receptors, with lower affinities in comparison to THC.[7][8] Because of its somewhat selective CB2 agonism, it is used experimentally as an immunosuppressant.

In contrast to tetrahydrocannabinol, it has no double bond isomers nor stereoisomers. It is not scheduled by Convention on Psychotropic Substances.