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- W2024252961 abstract "Summary The (R) - and (S) -4′-hydroxy-Δ 9 -tetrahydrocannabinols 1a,b (tetrahydrocannabinol = THC) were synthesized by the condensation of (+)- cis-p -menth-2-ene-1,8-diol 3 with the corresponding (R) - and (S) -4′-acetoxy olivetols 4a,b , followed by base hydrolysis. The optical purity of 1a,b was estimated to be >87% ee. Pharmacological data presented here indicate that 1a is two to three times more potent than 1b in vivo (locomotion, antinociception and catalepsy measures) and eight times more potent in its affinity for the cannabinoid CB 1 receptor. Additionally, data from catalepsy and hypothermia measures at both the normal and short time-course evaluations indicate that both isomers possess a short duration of action which is presumably due to rapid metabolism. A comparison of the biological activity of 3′- and 4′-hydroxy-Δ 9 -THCs indicates that although similar specificity resides in both the 3′- and 4′-positions, the 3′-position is more important than the 4′-position since (S) -3′-hydroxy-Δ 9 -THC is much more potent than (R) -4′-hydroxy-Δ 9 -THC. Furthermore 1b has an indication of a lead for separation of hypothermie effects from other pharmacological activities." @default.
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- W2024252961 date "1997-01-01" @default.
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- W2024252961 title "Synthesis and pharmacology of (R)- and (5)-4′-hydroxy-Δ9-tetrahydrocannabinols" @default.
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- W2024252961 doi "https://doi.org/10.1016/s0223-5234(97)87544-7" @default.
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