Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Experiment Videos

Stereochemical requirements for cannabimimetic activity.

R Mechoulam1, N Lander, M Srebnik

  • 1Department of Natural Products, Medical Faculty Hebrew University of Jerusalem, Israel.

NIDA Research Monograph
|January 1, 1987
PubMed
Summary

Stereochemistry is crucial for cannabinoid activity. Researchers found specific enantiomers of THC and its derivatives exhibit significantly different cannabimimetic and analgesic effects, achieving a dissociation of these properties.

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

The Long-Term Effect of a Quality Improvement Intervention in the Management of Bronchiolitis.

Indian pediatrics·2020
Same author

Long-Term Stability of Lorazepam in Sodium Chloride 0.9% Stored at Different Temperatures in Different Containers.

Hospital pharmacy·2020
Same author

A robust variant of block Jacobi-Davidson for extracting a large number of eigenpairs: Application to grid-based real-space density functional theory.

The Journal of chemical physics·2017
Same author

Racial inequality in the annual risk of Tuberculosis infection in the United States, 1910-1933.

Epidemiology and infection·2017
Same author

Classic IL-6R signalling is dispensable for intestinal epithelial proliferation and repair.

Oncogenesis·2016
Same author

[Visualization of the superior vena cava in the supraclavicular acoustic window].

Der Anaesthesist·2016

Area of Science:

  • Medicinal Chemistry
  • Pharmacology
  • Neuroscience

Background:

  • Cannabinoids, such as delta-3-THC and 7-OH-delta-6-THC, are known for their complex biological activities.
  • Understanding the structure-activity relationship (SAR) is key to developing targeted cannabinoid-based therapeutics.
  • Stereochemistry plays a critical role in the pharmacological effects of many drugs, including cannabinoids.

Purpose of the Study:

  • To review the SAR of cannabimimetic activity in cannabinoids, focusing on stereochemical requirements.
  • To present new findings on the differential activity of cannabinoid enantiomers.
  • To investigate the potential dissociation between cannabimimetic and analgesic effects.

Main Methods:

  • Review of existing literature on cannabinoid SAR.

Related Experiment Videos

  • Presentation of new experimental data on specific THC enantiomers.
  • Comparative analysis of enantiomeric activity in various animal models for cannabimimetic and analgesic effects.

    • Main Results:

    • In humans, (-)-(1S)-delta-3-THC is significantly more potent than (+)-(1R)-delta-3-THC.
    • For 7-OH-delta-6-THC DMH enantiomers, activity resides almost exclusively in the (-)-(3R, 4R) enantiomer (32).
    • The (3R,4R)-enantiomer (32) demonstrates higher activity than delta-1- or delta-6-THC in animal tests.
    • The inactive (+)-(3S,4S) enantiomer (33) exhibits potent analgesic properties.

    Conclusions:

    • Stereochemistry is a critical determinant of cannabimimetic activity in cannabinoids.
    • A complete dissociation between cannabimimetic and analgesic effects has been achieved with a specific cannabinoid enantiomer.
    • These findings have significant implications for the development of novel cannabinoid-based drugs with selective therapeutic profiles.