Synthesis and Isolation of Tetrahydrocannabinol Isomers
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.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jul 01, 1966
- Accession Number
- AD0486326
Entities
People
- Friedrich W. Hoffmann
- Richard L. Hively