SYNTHESIS AND ISOLATION OF TETRAHYDROCANNABINOL ISOMERS

In addition to cannabinol, cannabidiol, and trans-1-hydroxy-3-n-amyl-6, 6, 9 trimethyl-6a, 7, 8, 10a-tetrahydro-6-dibenzopyran (tetrahydrocannabinol A), a new marijuana constituent, trans-1-hydroxy-3-n-amyl-6, 6, 9-trimethyl-6a, 7, 10, 10a-tetrahydro 6-dibenzopyran (tetrahydrocannabinol B), was isol...

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Hauptverfasser:	Hively, Richard L, Hoffmann, Friedrich W
Format:	Report
Sprache:	eng
Schlagworte:	ABSORPTION AROMATIC COMPOUNDS CANNABINOLS CHEMICAL BONDS DEGRADATION DIENE SYNTHESIS HYDROCARBONS HYDROLYSIS MARIJUANA MELTING POINT MOLECULAR ISOMERISM NUCLEAR MAGNETIC RESONANCE Organic Chemistry OXIDATION PHENOLS PLASTICS PROTONS SYNTHESIS(CHEMISTRY) TEST METHODS THIN LAYER CHROMATOGRAPHY ULTRAVIOLET SPECTROSCOPY
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Zusammenfassung:	In addition to cannabinol, cannabidiol, and trans-1-hydroxy-3-n-amyl-6, 6, 9 trimethyl-6a, 7, 8, 10a-tetrahydro-6-dibenzopyran (tetrahydrocannabinol A), a new marijuana constituent, trans-1-hydroxy-3-n-amyl-6, 6, 9-trimethyl-6a, 7, 10, 10a-tetrahydro 6-dibenzopyran (tetrahydrocannabinol B), was isolated from Maryland and Mexican marijuana. Traces of tetrahydrocannabinol B were also found in Egyptian hashish. West Virginia marijuana contained only cannabidiolic acid. A second sample of Mexican marijuana furnished only tetrahydrocannabinol A and cannabinol, while a Spanish sample contained an additional amount of cannabidiol. The structure of tetrahydrocannabinol B was elucidated by chemical and spectral evidence. The partial syntheses of four isomeric tetrahydrocannabinols (A, B, and their cis-isomers) and the total synthesis of the racemic cis-isomer of tetrahydrocannabinol B are also described. (Author)