ArticlePsychopharmacology2015
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.
Article in Psychopharmacology, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 54 citations in OpenAlex.
- Investigating molecular and hemodynamic effects of LSD in the human brain.Nature neuroscience · 2026Article
- The working lives of neuronal 5-HTRSC chemical biology · 2026Review
- A Single Dose of a Psychedelic Drug Repairs Prefrontal Cortex Synaptic Physiology in a Mouse Model of Prenatal Alcohol Exposure.Brain and behavior · 2026Article
- Rewiring Receptor Activation: Mechanistic Insights into Toggle Switch Modulation by 25CN-NBx Compounds.ACS chemical neuroscience · 2026Article
- Psychedelic neuroplasticity of cortical neurons lacking 5-HT2A receptors.Molecular psychiatry · 2026Article
- Single-dose psychedelic enhances cognitive flexibility and reversal learning in mice weeks after administration.Psychedelics · 2025Article
- The Selective 5HTSynapse (New York, N.Y.) · 2025Article
- Psychedelic enhancement of flexible learning weeks after a single dose.bioRxiv : the preprint server for biology · 2024Article
- 5-hydroxytryptamine 2C/1A receptors modulate the biphasic dose response of the head twitch response and locomotor activity induced by DOM in mice.Psychopharmacology · 2024Article
- Cellular rules underlying psychedelic control of prefrontal pyramidal neurons.bioRxiv : the preprint server for biology · 2023Article
- Discovery of β-Arrestin-Biased 25CN-NBOH-Derived 5-HTJournal of medicinal chemistry · 2022Article
- The promises and perils of psychedelic pharmacology for psychiatry.Nature reviews. Drug discovery · 2022Review
- Automated Computer Software Assessment of 5-Hydroxytryptamine 2A Receptor-Mediated Head Twitch Responses from Video Recordings of Mice.ACS pharmacology & translational science · 2022Article
- DARK Classics in Chemical Neuroscience: NBOMes.ACS chemical neuroscience · 2020Review
- The Chronic Treatment With 5-HTNeurochemical research · 2020Article
- Article
- Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice.Journal of psychopharmacology (Oxford, England) · 2019Article
- Chronic treatment with a metabotropic mGlu2/3 receptor agonist diminishes behavioral response to a phenethylamine hallucinogen.Psychopharmacology · 2019Article
- Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HTBiochemical pharmacology · 2018Article
- Comparative neuropharmacology of N-(2-methoxybenzyl)-2,5-dimethoxyphenethylamine (NBOMe) hallucinogens and their 2C counterparts in male rats.Neuropharmacology · 2018Article
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6 authors at 4 institutions in 2 countries.
Funding
Abstract
rationale2-([2-(4-cyano-2,5-dimethoxyphenyl)ethylamino]methyl)phenol (25CN-NBOH) is structurally similar to N-benzyl substituted phenethylamine hallucinogens currently emerging as drugs of abuse. 25CN-NBOH exhibits dramatic selectivity for 5-HT2A receptors in vitro, but has not been behaviorally characterized.
objective25CN-NBOH was compared to the traditional phenethylamine hallucinogen R(-)-2,5-dimethoxy-4-iodoamphetamine (DOI) using mouse models of drug-elicited head twitch behavior and drug discrimination.
methodsDrug-elicited head twitches were quantified for 10 min following administration of various doses of either DOI or 25CN-NBOH, with and without pretreatments of 0.01 mg/kg 5-HT2A antagonist M100907 or 3.0 mg/kg 5-HT2C antagonist RS102221. The capacity of 25CN-NBOH to attenuate DOI-elicited head twitch was also investigated. Mice were trained to discriminate DOI or M100907 from saline, and 25CN-NBOH was tested for generalization.
results25CN-NBOH induced a head twitch response in the mouse that was lower in magnitude than that of DOI, blocked by M100907, but not altered by RS102221. DOI-elicited head twitch was dose-dependently attenuated by 25CN-NBOH pretreatment. 25CN-NBOH produced an intermediate degree of generalization (55 %) for the DOI training dose, and these interoceptive effects were attenuated by M100907. Finally, 25CN-NBOH did not generalize to M100907 at any dose, but ketanserin fully substituted in these animals.
conclusions25CN-NBOH was behaviorally active, but less effective than DOI in two mouse models of hallucinogenic effects. The effectiveness with which M100907 antagonized the behavioral actions of 25CN-NBOH strongly suggests that the 5-HT2A receptor is an important site of agonist action for this compound in vivo.
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