ArticleACS chemical neuroscience2014
Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists.
Article in ACS chemical neuroscience, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 53 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
53 citing papers in PubMed.
- Article
- Rewiring Receptor Activation: Mechanistic Insights into Toggle Switch Modulation by 25CN-NBx Compounds.ACS chemical neuroscience · 2026Article
- Improved synthesis and physicochemical characterization of the selective serotonin 2A receptor agonist 25CN-NBOH.Beilstein journal of organic chemistry · 2026Article
- Discovery of Highly Selective 5-HTJournal of medicinal chemistry · 2025Article
- Serotonin receptor 5-HTJournal for immunotherapy of cancer · 2025Article
- The Selective Serotonin 5‑HTACS pharmacology & translational science · 2025Article
- Single-dose psychedelic enhances cognitive flexibility and reversal learning in mice weeks after administration.Psychedelics · 2025Article
- Locomotor and discriminative stimulus effects of NBOH hallucinogens in rodents.Behavioural pharmacology · 2025Article
- The Selective 5HTSynapse (New York, N.Y.) · 2025Article
- Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride.Beilstein journal of organic chemistry · 2025Article
- Receptor interaction profiles of 4-alkoxy-2,6-dimethoxyphenethylamines (Ψ derivatives) and related amphetamines.Frontiers in pharmacology · 2025Article
- Psychedelic enhancement of flexible learning weeks after a single dose.bioRxiv : the preprint server for biology · 2024Article
- 1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane (DOI): From an Obscure to Pivotal Member of the DOX Family of Serotonergic Psychedelic Agents - A Review.ACS pharmacology & translational science · 2024Review
- The novel psychoactive substance 25E-NBOMe induces reward-related behaviors via dopamine D1 receptor signaling in male rodents.Archives of pharmacal research · 2024Article
- Exploring Novel Antidepressants Targeting G Protein-Coupled Receptors and Key Membrane Receptors Based on Molecular Structures.Molecules (Basel, Switzerland) · 2024Review
- Identification of 5-HTNature communications · 2023Article
- A molecular analysis of substituted phenylethylamines as potential microtubule targeting agents through in silico methods and in vitro microtubule-polymerization activity.Scientific reports · 2023Article
- Structure-Activity Assessment and In-Depth Analysis of Biased Agonism in a Set of Phenylalkylamine 5-HTACS chemical neuroscience · 2023Article
- G protein-coupled receptors as targets for transformative neuropsychiatric therapeutics.American journal of physiology. Cell physiology · 2023Review
- On the construction of LIECE models for the serotonin receptor 5-HTJournal of computer-aided molecular design · 2023Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
7 authors.
Funding
Abstract
N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5-dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule to determine the effects on receptor binding affinity and functional activity at 5-HT2A and 5-HT2C receptors. The compounds generally had high affinity for the 5-HT2A receptor with 8b having the highest affinity at 0.29 nM but with several other compounds also exhibiting subnanomolar binding affinities. The functional activity of the compounds was distributed over a wider range with 1b being the most potent at 0.074 nM. Most of the compounds exhibited low to moderate selectivity (1- to 40-fold) for the 5-HT2A receptor in the binding assays, although one compound 6b showed an impressive 100-fold selectivity for the 5-HT2A receptor. In the functional assay, selectivity was generally higher with 1b being more than 400-fold selective for the 5-HT2A receptor.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.