ArticleACS chemical neuroscience2013
Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands.
Article in ACS chemical neuroscience, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
24 citing papers in PubMed.
- Transforming Amino Acids into Serotonin 5-HTJournal of the American Chemical Society · 2025Article
- Discovery of Highly Selective 5-HTJournal of medicinal chemistry · 2025Article
- Design, Synthesis, and In Vitro Characterization of a Tryptamine-Based Visible-Light Photoswitchable 5-HTJournal of medicinal chemistry · 2025Article
- Receptor interaction profiles of 4-alkoxy-2,6-dimethoxyphenethylamines (Ψ derivatives) and related amphetamines.Frontiers in pharmacology · 2025Article
- Discovery and Structure-Activity Relationships of 2,5-Dimethoxyphenylpiperidines as Selective Serotonin 5-HTJournal of medicinal chemistry · 2024Article
- Evaluation of the Indazole Analogs of 5-MeO-DMT and Related Tryptamines as Serotonin Receptor 2 Agonists.ACS medicinal chemistry letters · 2024Article
- Identification of 5-HTNature communications · 2023Article
- Introducing Conformational Restraints on 25CN-NBOH: A Selective 5-HTACS medicinal chemistry letters · 2023Article
- Discovery of β-Arrestin-Biased 25CN-NBOH-Derived 5-HTJournal of medicinal chemistry · 2022Article
- International Union of Basic and Clinical Pharmacology. CX. Classification of Receptors for 5-hydroxytryptamine; Pharmacology and Function.Pharmacological reviews · 2021Review
- Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines.Frontiers in pharmacology · 2021Article
- Synthesis of Vicinal Quaternary All-Carbon Centers via Acid-catalyzed Cycloisomerization of Neopentylic Epoxides.Organic letters · 2020Article
- Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species.Neuropharmacology · 2020Article
- NBOMes-Highly Potent and Toxic Alternatives of LSD.Frontiers in neuroscience · 2020Review
- Article
- Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran ("FLY") and benzodifuran ("DragonFLY") analogs.Neuropharmacology · 2019Article
- Locomotor and discriminative stimulus effects of four novel hallucinogens in rodents.Behavioural pharmacology · 2017Article
- Lithium Enolates Derived from Weinreb Amides: Insights into Five-Membered Chelate Rings.The Journal of organic chemistry · 2016Article
- N-Benzyl-5-methoxytryptamines as Potent Serotonin 5-HT2 Receptor Family Agonists and Comparison with a Series of Phenethylamine Analogues.ACS chemical neuroscience · 2015Article
- Hallucinogen-like effects of 2-([2-(4-cyano-2,5-dimethoxyphenyl) ethylamino]methyl)phenol (25CN-NBOH), a novel N-benzylphenethylamine with 100-fold selectivity for 5-HT₂A receptors, in mice.Psychopharmacology · 2015Article
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Authors and funding
9 authors.
Funding
Abstract
Based on the structure of the superpotent 5-HT(2A) agonist 2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine, which consists of a ring-substituted phenethylamine skeleton modified with an N-benzyl group, we designed and synthesized a small library of constrained analogues to identify the optimal arrangement of the pharmacophoric elements of the ligand. Structures consisted of diversely substituted tetrahydroisoquinolines, piperidines, and one benzazepine. Based on the structure of (S,S)-9b, which showed the highest affinity of the series, we propose an optimal binding conformation. (S,S)-9b also displayed 124-fold selectivity for the 5-HT(2A) over the 5-HT(2C) receptor, making it the most selective 5-HT(2A) receptor agonist ligand currently known.
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Registered trials
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