ArticleJournal of medicinal chemistry2015
Probing the carboxyester side chain in controlled deactivation (-)-δ(8)-tetrahydrocannabinols.
Article in Journal of medicinal chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Cannabinoids as Multitarget Drugs for the Treatment of Autoimmunity in Glaucoma.ACS pharmacology & translational science · 2025Review
- Virtual Screening of a Chemically Diverse "Superscaffold" Library Enables Ligand Discovery for a Key GPCR Target.ACS chemical biology · 2024Article
- The endocannabinoid system and breathing.Frontiers in neuroscience · 2023Review
- Understanding the Dynamics of the Structural States of Cannabinoid Receptors and the Role of Different Modulators.Life (Basel, Switzerland) · 2022Article
- Article
- Cannabinoid-2 Agonism with AM2301 Mitigates Morphine-Induced Respiratory Depression.Cannabis and cannabinoid research · 2021Article
- Article
- Synthesis of Functionalized Cannabilactones.Molecules (Basel, Switzerland) · 2020Article
- Chain Substituted Cannabilactones with Selectivity for the CB2 Cannabinoid Receptor.Molecules (Basel, Switzerland) · 2019Article
- Controlled-Deactivation CB1 Receptor Ligands as a Novel Strategy to Lower Intraocular Pressure.Pharmaceuticals (Basel, Switzerland) · 2018Article
- Novel C-Ring-Hydroxy-Substituted Controlled Deactivation Cannabinergic Analogues.Journal of medicinal chemistry · 2016Article
- The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation.Perspectives in medicinal chemistry · 2016Article
- Molecular-interaction and signaling profiles of AM3677, a novel covalent agonist selective for the cannabinoid 1 receptor.ACS chemical neuroscience · 2015Article
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Authors and funding
16 authors.
Funding
Abstract
We recently reported on a controlled deactivation/detoxification approach for obtaining cannabinoids with improved druggability. Our design incorporates a metabolically labile ester group at strategic positions within the THC structure. We have now synthesized a series of (-)-Δ(8)-THC analogues encompassing a carboxyester group within the 3-alkyl chain in an effort to explore this novel cannabinergic chemotype for CB receptor binding affinity, in vitro and in vivo potency and efficacy, as well as controlled deactivation by plasma esterases. We have also probed the chain's polar characteristics with regard to fast onset and short duration of action. Our lead molecule, namely 2-[(6aR,10aR)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-3-yl]-2-methyl-propanoic acid 3-cyano-propyl ester (AM7438), showed picomolar affinity for CB receptors and is deactivated by plasma esterases while the respective acid metabolite is inactive. In further in vitro and in vivo experiments, the compound was found to be a remarkably potent and efficacious CB1 receptor agonist with relatively fast onset/offset of action.
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