Structural Formula Vector Image
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°

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