Accession Number : AD0486326

Title :   SYNTHESIS AND ISOLATION OF TETRAHYDROCANNABINOL ISOMERS.

Descriptive Note : Technical rept. Jan 63-Mar 65,

Corporate Author : EDGEWOOD ARSENAL ABERDEEN PROVING GROUND MD

Personal Author(s) : Hively, Richard L. ; Hoffmann, Friedrich W.

Report Date : JUL 1966

Pagination or Media Count : 119

Abstract : 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)

Descriptors :   (*CANNABINOLS, SYNTHESIS(CHEMISTRY)), PLASTICS, DIENE SYNTHESIS, HYDROLYSIS, PHENOLS, ULTRAVIOLET SPECTROSCOPY, MOLECULAR ISOMERISM, TEST METHODS, NUCLEAR MAGNETIC RESONANCE, CHEMICAL BONDS, THIN LAYER CHROMATOGRAPHY, DEGRADATION, AROMATIC COMPOUNDS, MELTING POINT, PROTONS, OXIDATION, ABSORPTION, HYDROCARBONS.

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE