Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs

@article{Martin1991BehavioralBA,
  title={Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs},
  author={Billy R. Martin and David R Compton and Brian F Thomas and William R. Prescott and Patrick J. Little and Raj Kumar Razdan and M.Ross Johnson and Lawrence S. Melvin and Raphael Mechoulam and J. WardSusan},
  journal={Pharmacology Biochemistry and Behavior},
  year={1991},
  volume={40},
  pages={471-478}
}
Novel pyrazole cannabinoids: insights into CB(1) receptor recognition and activation.
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Results suggest that the structural properties of 1- and 5-substituents are primarily responsible for the antagonist activity of SR141716A.
Structure-activity relationships of indole- and pyrrole-derived cannabinoids.
TLDR
A series of indole- and pyrrole-derived cannabinoids was developed, in which the morpholinoethyl group was replaced with another cyclic structure or with a carbon chain that more directly corresponded to the side chain of Delta9-THC and were tested for CB1 binding affinity and in a battery of in vivo tests.
Structure-Activity Relationships of Indole-and Pyrrole-Derived Cannabinoids 1
TLDR
This study shows that the pharmacological effects of D-THC and WIN 55,212 are blocked by the cannabinoid antagonist, SR 141716A, and chronic administration results in cross-tolerance to the hypomobility, hypothermia, antinociceptive and cataleptic effects of these structurally distinct cannabinoids.
1-Pentyl-3-phenylacetylindoles and JWH-018 share in vivo cannabinoid profiles in mice.
Combination Chemistry: Structure-Activity Relationships of Novel Psychoactive Cannabinoids.
TLDR
This chapter focuses on integration of recent results with those covered in previous reviews, including tetramethylcyclopropyl ketones and indazole-derived cannabinoids, which are currently popular synthetic cannabinoids.
Pentyl-3-phenylacetylindoles and JWH-018 share in vivo cannabinoid profiles n mice
TLDR
The results suggest that phenylacetylindoles with good CB1 binding affinity share pharmacological properties with THC in mice; however, they also emphasize the complexity of molecular interactions of synthetic cannabinoids with CB1 receptors and suggest that scheduling efforts based solely upon structural manipulation should be considered.
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The pharmacological effects of three stereoisomeric pairs of structurally novel cannabinoids were tested after i.v. administration in mice for depression of spontaneous activity and the production of hypothermia, antinociception and catalepsy to demonstrate the high degree of enantioselectivity and potency.
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TLDR
The goals of the studies described herein were to determine whether these bicyclic analogs possess similar pharmacological properties of delta 9-THC, to compare pharmacological activity after s.c. and i.v. administration, and to evaluate the structure-activity relationship of this series of analogs for further insight into cannabinoid mechanism of action.
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TLDR
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TLDR
These analogues, which possess only a portion of the full pharmacological spectrum of activity of delta 9-THC, indicate that cannabinoid-mediated reduction of spontaneous locomotor activity, hypothermia, antinociception, and/or catalepsy need not be produced simultaneously, possibly suggesting the existence of more than one mechanism of action.
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TLDR
A conformational analysis of the major active constituent of marijuana and its analogs is described and conclusions are reached, concerning the conformation of the pyran ring, the preferred orientation of the phenolic O-H bond, and ring C conformational preferences in 1, 2, 3, and A-THC, are in substantial agreement with pmr observations resulting from nuclear Overhauser effect and solvent effect studies.
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TLDR
The criteria for a high affinity, stereoselective, pharmacologically distinct cannabinoid receptor in brain tissue have been fulfilled.
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