Enantiomeric cannabinoids: stereospecificity of psychotropic activity

  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},
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). 
Cannabinoids: structures, effects, and classification
The data on the chemical structures, biological effects, and use of cannabinoids on the illegal market of new psychoactive substances were generalized. An extended classification comprising new
Structure–Activity Relationships of Classical Cannabinoids
In this chapter an overview of the more recent developments in the structure–activity relationships (SARs) of classical cannabinoids is discussed, especially the profound pharmacological effects
Early phytocannabinoid chemistry to endocannabinoids and beyond
There have since been considerable advances in understanding of the endocannabinoid system and its function in the brain, which reveal potential therapeutic targets for a wide range of brain disorders.
The endocannabinoid system and the brain.
Research on the actions of the endocannabinoid system on anxiety, depression, neurogenesis, reward, cognition, learning, and memory, and the effects are at times biphasic--lower doses causing effects opposite to those seen at high doses.
Novel natural and synthetic ligands of the endocannabinoid system.
It is concluded that further synthetic work based on both the plant cannabinoids and on the endocannabinoids may lead to novel therapeutics and that the identification and the elucidation of the biological profile of the myriad of endogenous N-acyl amino acids and related compounds may enhance the already wide spectrum of lipidomics.
Medicinal Chemistry Endeavors around the Phytocannabinoids
This review summarizes past as well as recent developments in the structure–activity relationships of phytocannabinoids.
Derivatives of Dexanabinol. I. Water-Soluble Salts of Glycinate Esters
The neuroprotecting properties manifested by some of the new derivatives were associated with very low neuronal cell toxicity and are credited to parent compound released by hydrolysis during the experiments rather than to intrinsic activity.
Identification and structural elucidation of four cannabimimetic compounds (RCS-4, AM-2201, JWH-203 and JWH-210) in seized products.
The structural and spectral elucidation of four cannabimimetic compounds seized in Belgium are reported, which allowed the detection of illicit compounds for which reference materials were not available.
Synthetic Strategies for (-)-Cannabidiol and Its Structural Analogs.
This review concisely summarizes the historic and recent milestones in the synthetic strategies for (-)-CBD and its analogs and generates novel (--CBD analogs that exhibit advanced biological activities.


Hypothalamo-hypophyseal-gonadal function in the rat following administration of the novel and selective D-1 agonist CY 208-243
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
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
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