A6-Tetrahydrocannabinol

Previous work with A6-Tetrahydrocannabinol [(3R,4R) 6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-l -ol, hereinafter referred to as A6-THC], has indicated that derivatives of this compound may prove clinically useful. The 7-carboxy derivative of A6-THC [A6-THC-7-oic acid] has been reported to be a non-psychoactive, potent antagonist to endogenous platelet activating factor and, thus, a useful treatment for PAF-induced disorders, such as asthma, systemic anaphylaxis, and septic shock. (U.S. Pat. No. 4,973,603, issued Nov. 27, 1990 to Sumner Burstein). Another derivative, (3S,4S)-7-hydroxy-A6-THC-l,l-dimethylheptyl, has been reported to possess analgesic and antiemetic activities. (U.S. Pat. No. 4,876,276). 

THC refers to tetrahydrocannabinol, and A refers to the position of the double bond. Various numbering systems are used, so the following equivalences should be noted A THC = A 3,4-trans-THC = A9THC and A6THC = AH6)THC = A8THC = A6-3,4-trans-THC. 

The X-ray crystal structure of A1 -tetrahydrocannabinolic acid B is reported,362 and one of the previously reported (Vol. 4, p. 75) dihydrobenzofurans from the citric acid-catalysed condensation of orcinol with menth-4-en-3-ol is shown to be (256) by X-ray analysis.363 G.c.-m.s. assay of A -THC-OMe allows the detection of 1 ng mP1 plasma of A -THC.364 The mass spectral fragmentation of A -THC, A6-THC, and some isomeric cannabinoids to the prominent m/e 231 ion has been examined.365 Miniaturized syntheses of 32 natural, or potentially natural, cannabinoids are reported in connection with their chromatographic analysis.366... 

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