Enantiomeric cannabinoids: stereospecificity of psychotropic activity

@article{Mechoulam2005EnantiomericCS,
  title={Enantiomeric cannabinoids: stereospecificity of psychotropic activity},
  author={Raphael Mechoulam and Jeffrey J. Feigenbaum and Naftali Lander and Mark Segal and Torbj{\"o}rn U. C. J{\"a}rbe and Arto J Hiltunen and Paul F. Consroe},
  journal={Experientia},
  year={2005},
  volume={44},
  pages={762-764}
}
The 1,1-dimethylheptyl homolog of (−)-(3R,4R)-7-hydroxy-delta-6-tetrahydrocannabinol (compoundII) is highly psychotropic in mice, rats and pigeons. The (+)-(3S,4S) enantiomer (III) was found to be psychotropically inactive at doses up to several thousand times those of the ED50 of (II). 
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References

SHOWING 1-10 OF 10 REFERENCES
Hypothalamo-hypophyseal-gonadal function in the rat following administration of the novel and selective D-1 agonist CY 208-243
TLDR
D-1 receptor activation by systemic drug administration does not alter HHG function in rats, and the effects of the novel and selective dopamine D-1 agonist CY 208-243 on the rat hypothalamo-hypophyseal-gonadal axis were studied.
The ring test: a quantitative method for assessing the ‘cataleptic’ effect of cannabis in mice
  • R. Pertwee
  • Biology, Medicine
    British journal of pharmacology
  • 1972
TLDR
It is concluded that Δ1‐tetrahydrocannabinol (Δ1‐THC) is largely responsible for the effect of cannabis extract on mobility; the potency ratio of Δ1-THC to cannabis extract is between 10 and 20.
Cannabidiol--antiepileptic drug comparisons and interactions in experimentally induced seizures in rats.
  • P. Consroe, A. Wolkin
  • Biology, Psychology
    The Journal of pharmacology and experimental therapeutics
  • 1977
TLDR
CBD is an effective anticonvulsant with a specificity more comparable to drugs clinically effective in major than minor seizures, and it appears that CBD enhances the anticonVulsant effects of the former and reduces the effects ofThe latter types of antiepileptic drugs.
A repeated tests procedure to assess onset and duration of the cue properties of (−)Δ9-THC, (−)Δ8-THC-DMH and (+)Δ8-THC
Rats were trained in a two-lever operant box in a drug discrimination procedure to respond differentially to the effects induced by 3 mg/kg of (-)Δ9-tetrahydrocannabinol and the drug vehicle. Tests