Analytical Chemistry and Spectroscopy
Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
The stereospecific elimination of the 3-deuterium atom from metabolites of [2H]-analogues of Δ1-tetrahydrocannabinol (Δ1-THC), Δ6-THC and Δ7-THC has been investigated as a possible method for determining the stereochemistry of metabolites substituted with hydroxy or acid groups in the terpene ring. Elimination of HCOOTMS was found to involve the 3-hydrogen of the axial but not the equatorial isomer of hexahydrocannabinol-7-oic acid, a metabolite of all three cannabinoids. Similar stereospecific eliminations were observed during the loss of TMSOH from the TMS derivatives of 5α-hydroxy-Δ6-THC, 6α-hydroxy-Δ1-THC and 1α,2β-dihydroxy-Δ1-THC. Loss of TMSOH from 1α,7- and 1β,7-dihydroxy-HHC involved the 3-hydrogen in both cases but the isomers could be distinguished as their alkane-boronate derivatives; only the derivative of 1α,7-dihydroxy-HHC lost the boronate ring with stereospecific removal of the 3-hydrogen. The stereochemistry of the four isomers of 1,6-dihydroxy-HHC could not be determined in this way as the [M-TMSOH]+· ions from all four compounds had lost the 3-hydrogen, presumably as the result of 1,6-bond cleavage.
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