3'-Hydroxy- and (.+-.)-3',11-dihydroxy-.DELTA.9-tetrahydrocannabinol: (THC) biologically active metabolites of .DELTA.9-tetrahydrocannabinol

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Abstract
Synthesis of 3''-hydroxy- and (.+-.)-3'',11-dihydroxy-.DELTA.9-tetrahydrocannabinol [THC] [the active constituent of marijuana], metabolites of .DELTA.9-THC, is described. The metabolites were compared with .DELTA.9-THC for their ability to depress spontaneous activity and rectal temperature in mice and for their effects on overt behavior in dogs. 3''-Hydroxy-.DELTA.9-THC was also compared to .DELTA.9-THC in the mouse symptomatology test and cardiovascular system in dogs. The metabolites produced pharmacological effects similar to those of .DELTA.9-THC in all tests. 3''-Hydroxy-.DELTA.9-THC was 2-3 times more effective than .DELTA.9-THC in the behavioral tests, whereas (.+-.)-3'',11-dihydroxy-.DELTA.9-THC was approximately 3 times less active than .DELTA.9-THC.