Stereochemical effects of 11-OH-Δ 8-tetrahydrocannabinol-dimethylheptyl to inhibit adenylate cyclase and bind to the cannabinoid receptor

@article{Howlett1990StereochemicalEO,
  title={Stereochemical effects of 11-OH-$\Delta$
 8-tetrahydrocannabinol-dimethylheptyl to inhibit adenylate cyclase and bind to the cannabinoid receptor},
  author={Allyn C. Howlett and T. M. Champion and Gerald H. Wilken and Raphael Mechoulam},
  journal={Neuropharmacology},
  year={1990},
  volume={29},
  pages={161-165}
}
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120 Citations
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120 Citations

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References

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Stereochemical effects of 11-OH-Δ 8-THC-dimethylheptyl in mice and dogs
High-affinity cannabinoid binding sites in brain membranes labeled with [3H]-5'-trimethylammonium delta 8-tetrahydrocannabinol.
TLDR
The binding of [3H]-5'-trimethylammonium delta 8-tetrahydrocannabinol (THC) [( 3H]TMA) to rat neuronal membranes was studied and it was found that several nonpsychotropic cannabinoids are active at the binding site.
Comparative Pharmacology of Δ9-Tetrahydrocannabinol and its Metabolite, 11-OH-Δ9-Tetrahydrocannabinol
TLDR
It is suggested that in man, A9-THC, the active constituent in marihuana, is converted to 11-OHY9-Tetrahydrocannabinol, which is in part responsible for the psychologic effects.
Stereochemical requirements for cannabimimetic activity.
TLDR
A complete dissociation between the cannabimimetic and the analgetic effects in a cannabinoid has been achieved, apparently for the first time.
Contribution of the metabolite 7-hydroxy-Δ1-tetrahydrocannabinol towards the pharmacological activity of Δ1tetrahydrocannabinol in mice
Cannabinoid inhibition of adenylate cyclase: Relative activity of constituents and metabolites of marihuana
  • A. Howlett
  • Biology, Chemistry
    Neuropharmacology
  • 1987
Regulation of adenylate cyclase by chronic exposure to cannabimimetic drugs.
TLDR
A comprehensive investigation of cellular effects of chronic exposure to cannabimimetic agents found that cannabinoid-treated cells did not significantly affect cell growth rate or protein content per cell, and their morphology was not altered at the light or the electron microscope level.
Determination and characterization of a cannabinoid receptor in rat brain.
TLDR
The criteria for a high affinity, stereoselective, pharmacologically distinct cannabinoid receptor in brain tissue have been fulfilled.
Nonclassical cannabinoid analgetics inhibit adenylate cyclase: development of a cannabinoid receptor model.
TLDR
It is postulated that the receptor that is associated with the regulation of adenylate cyclase in vitro may be the same receptor as that mediating analgesia in vivo, and a conceptualization of the cannabinoid analgetic receptor is presented.
Cannabinoid inhibition of adenylate cyclase. Pharmacology of the response in neuroblastoma cell membranes.
TLDR
Inhibition of adenylate cyclase was specific for psychoactive cannabinoids, since cannabinol and cannabidiol produced minimal or no response, and was also stereoselective, since dextronantradol did not produce the response.
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