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Literature DB >> 3416993

Enantiomeric cannabinoids: stereospecificity of psychotropic activity.

R Mechoulam¹, J J Feigenbaum, N Lander, M Segal, T U Järbe, A J Hiltunen, P Consroe.

Abstract

The 1,1-dimethylheptyl homolog of (-)-(3R,4R)-7-hydroxy-delta-6- tetrahydrocannabinol (compound II) 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).

Entities: Chemical Species

Mesh：

Substances：
Cannabinoids

Year: 1988 PMID： 3416993 DOI： 10.1007/BF01959156

Source DB: PubMed Journal: Experientia ISSN： 0014-4754

9 in total

Review 1. Structure-activity relationships in cannabinoids.

Authors: R K Razdan
Journal: Pharmacol Rev Date: 1986-06 Impact factor: 25.468

2. Cannabimimetic activity (delta 1-THC cue) of cannabidiol monomethyl ether and two stereoisomeric hexahydrocannabinols in rats and pigeons.

Authors: T U Järbe; A J Hiltunen; N Lander; R Mechoulam
Journal: Pharmacol Biochem Behav Date: 1986-08 Impact factor: 3.533

3. Interactions between delta 9-tetrahydrocannabinol and cannabidiol as evaluated by drug discrimination procedures in rats and pigeons.

Authors: A J Hiltunen; T U Järbe
Journal: Neuropharmacology Date: 1986-02 Impact factor: 5.250

4. The ring test: a quantitative method for assessing the 'cataleptic' effect of cannabis in mice.

Authors: R G Pertwee
Journal: Br J Pharmacol Date: 1972-12 Impact factor: 8.739

Review 5. Cannabinoid pharmacology.

Authors: W L Dewey
Journal: Pharmacol Rev Date: 1986-06 Impact factor: 25.468

6. A stereospecific synthesis of (-)-delta 1- and (-)-delta 1(6)-tetrahydrocannabinols.

Authors: R Mechoulam; P Braun; Y Gaoni
Journal: J Am Chem Soc Date: 1967-08-16 Impact factor: 15.419

7. A repeated test procedure to assess onset and duration of the cue properties of (-) delta 9-THC, (-) delta 8-THC-DMH and (+) delta 8-THC.

Authors: T U Järbe; M D Swedberg; R Mechoulam
Journal: Psychopharmacology (Berl) Date: 1981 Impact factor: 4.530

Review 8. Cellular effects of cannabinoids.

Authors: B R Martin
Journal: Pharmacol Rev Date: 1986-03 Impact factor: 25.468

9. Cannabidiol--antiepileptic drug comparisons and interactions in experimentally induced seizures in rats.

Authors: P Consroe; A Wolkin
Journal: J Pharmacol Exp Ther Date: 1977-04 Impact factor: 4.030

9 in total

26 in total

1. CB2 cannabinoid receptor agonist, JWH-015, triggers apoptosis in immune cells: potential role for CB2-selective ligands as immunosuppressive agents.

Authors: Catherine Lombard; Mitzi Nagarkatti; Prakash Nagarkatti
Journal: Clin Immunol Date: 2006-12-20 Impact factor: 3.969

2. Cannabinoids in disguise: Δ9-tetrahydrocannabinol-like effects of tetramethylcyclopropyl ketone indoles.

Authors: Jenny L Wiley; Julie A Marusich; Timothy W Lefever; Megan Grabenauer; Katherine N Moore; Brian F Thomas
Journal: Neuropharmacology Date: 2013-08-02 Impact factor: 5.250

3. Nonpsychotropic cannabinoid acts as a functional N-methyl-D-aspartate receptor blocker.

Authors: J J Feigenbaum; F Bergmann; S A Richmond; R Mechoulam; V Nadler; Y Kloog; M Sokolovsky
Journal: Proc Natl Acad Sci U S A Date: 1989-12 Impact factor: 11.205

4. Efficacy of Cannabinoids in a Pre-Clinical Drug-Screening Platform for Alzheimer's Disease.

Authors: David Schubert; Devin Kepchia; Zhibin Liang; Richard Dargusch; Joshua Goldberg; Pamela Maher
Journal: Mol Neurobiol Date: 2019-05-19 Impact factor: 5.590

Review 5. The Endocannabinoid System and Heart Disease: The Role of Cannabinoid Receptor Type 2.

Authors: Makenzie L Fulmer; Douglas P Thewke
Journal: Cardiovasc Hematol Disord Drug Targets Date: 2018

Review 6. Selective modulation of the cannabinoid type 1 (CB₁) receptor as an emerging platform for the treatment of neuropathic pain.

Authors: Samuel D Banister; Kaavya Krishna Kumar; Vineet Kumar; Brian K Kobilka; Sanjay V Malhotra
Journal: Medchemcomm Date: 2019-03-18 Impact factor: 3.597

7. Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide.

Authors: T Bisogno; L Hanus; L De Petrocellis; S Tchilibon; D E Ponde; I Brandi; A S Moriello; J B Davis; R Mechoulam; V Di Marzo
Journal: Br J Pharmacol Date: 2001-10 Impact factor: 8.739

Enantiomeric cannabinoids: stereospecificity of psychotropic activity.

Review 1. Structure-activity relationships in cannabinoids.

2. Cannabimimetic activity (delta 1-THC cue) of cannabidiol monomethyl ether and two stereoisomeric hexahydrocannabinols in rats and pigeons.

3. Interactions between delta 9-tetrahydrocannabinol and cannabidiol as evaluated by drug discrimination procedures in rats and pigeons.

4. The ring test: a quantitative method for assessing the 'cataleptic' effect of cannabis in mice.

Review 5. Cannabinoid pharmacology.

6. A stereospecific synthesis of (-)-delta 1- and (-)-delta 1(6)-tetrahydrocannabinols.

7. A repeated test procedure to assess onset and duration of the cue properties of (-) delta 9-THC, (-) delta 8-THC-DMH and (+) delta 8-THC.

Review 8. Cellular effects of cannabinoids.

9. Cannabidiol--antiepileptic drug comparisons and interactions in experimentally induced seizures in rats.

1. CB2 cannabinoid receptor agonist, JWH-015, triggers apoptosis in immune cells: potential role for CB2-selective ligands as immunosuppressive agents.

2. Cannabinoids in disguise: Δ9-tetrahydrocannabinol-like effects of tetramethylcyclopropyl ketone indoles.

3. Nonpsychotropic cannabinoid acts as a functional N-methyl-D-aspartate receptor blocker.

4. Efficacy of Cannabinoids in a Pre-Clinical Drug-Screening Platform for Alzheimer's Disease.

Review 5. The Endocannabinoid System and Heart Disease: The Role of Cannabinoid Receptor Type 2.

Review 6. Selective modulation of the cannabinoid type 1 (CB₁) receptor as an emerging platform for the treatment of neuropathic pain.

7. Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide.

8. Endocannabinoid signaling in neurotoxicity and neuroprotection.

Review 9. Pharmacology of traumatic brain injury: where is the "golden bullet"?

Review 10. What we know and do not know about the cannabinoid receptor 2 (CB2).

Review 1. Structure-activity relationships in cannabinoids.

Review 5. Cannabinoid pharmacology.

Review 8. Cellular effects of cannabinoids.

Review 5. The Endocannabinoid System and Heart Disease: The Role of Cannabinoid Receptor Type 2.

Review 6. Selective modulation of the cannabinoid type 1 (CB1) receptor as an emerging platform for the treatment of neuropathic pain.

Review 9. Pharmacology of traumatic brain injury: where is the "golden bullet"?

Review 10. What we know and do not know about the cannabinoid receptor 2 (CB2).

Review 6. Selective modulation of the cannabinoid type 1 (CB₁) receptor as an emerging platform for the treatment of neuropathic pain.