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A novel probe for the cannabinoid receptor.

W A Devane1, A Breuer, T Sheskin

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

Journal of Medicinal Chemistry
|May 29, 1992
PubMed
Summary

The potent 1,1-dimethylheptyl (DMH) homologue of 7-hydroxy-delta 6-tetrahydrocannabinol was synthesized and tested. This compound exhibits high affinity for cannabinoid receptors, making it a valuable research tool.

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Area of Science:

  • Medicinal Chemistry
  • Pharmacology
  • Neuroscience

Background:

  • The 1,1-dimethylheptyl (DMH) homologue of 7-hydroxy-delta 6-tetrahydrocannabinol (3) is a highly potent cannabimimetic.
  • Cannabinoid receptor ligands are crucial for understanding the endocannabinoid system.

Purpose of the Study:

  • To synthesize and characterize epimers of 5'-(1,1-dimethylheptyl)-7-hydroxyhexahydrocannabinol.
  • To evaluate the binding affinity and functional potency of these novel cannabinoid receptor ligands.

Main Methods:

  • Hydrogenation of compound 3 using various catalysts and conditions.
  • In vivo cannabinoid receptor discrimination studies in pigeons.
  • Radioligand binding assays to determine receptor affinity (KD and Ki values).

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Main Results:

  • Synthesis yielded equatorial (7) and axial (8) epimers of 5'-(1,1-dimethylheptyl)-7-hydroxyhexahydrocannabinol.
  • Compound 7 demonstrated high potency in pigeons, discriminating for delta 1-THC (ED50 = 0.002 mg/kg).
  • Compound 7 exhibited a high affinity for the cannabinoid receptor (KD = 45 pM), surpassing known ligands like CP-55940.

Conclusions:

  • Compound 7 is a potent and selective cannabinoid receptor ligand.
  • Tritiated compound 7 serves as a novel radioligand for cannabinoid receptor research.
  • These findings contribute to the development of new tools for studying cannabinoid receptor pharmacology.