ArticleNeuropharmacology2014
Effects of the hallucinogen 2,5-dimethoxy-4-iodophenethylamine (2C-I) and superpotent N-benzyl derivatives on the head twitch response.
Article in Neuropharmacology, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 64 papers, 1 of them a synthesis that pooled it.
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Who cites it
64 citing papers in PubMed, 1 synthesis or guideline pooled it.
- Toxicities associated with NBOMe ingestion-a novel class of potent hallucinogens: a review of the literature.PsychosomaticsPooled it
- Role of β-Arrestin2 Signaling in Neuropharmacological Effects of Psychedelic Drugs.ACS chemical neuroscience · 2026Article
- No evidence for direct physical interaction of 5-HTbioRxiv : the preprint server for biology · 2026Article
- The serotonin 1B receptor is required for some of the behavioral effects of psilocybin in mice.Molecular psychiatry · 2026Article
- The psychedelic phenethylamine 25C-NBF, a selective 5-HT2A agonist, shows psychoplastogenic properties and rapid antidepressant effects in male rodents.Molecular psychiatry · 2026Article
- The 4-alkyl chain length of 2,5-dimethoxyamphetamines differentially affects in vitro serotonin receptor actions versus in vivo psychedelic-like effects.Molecular psychiatry · 2026Article
- Mind the gap! Addressing unresolved aspects of abuse potential evaluation and scheduling of classic and novel psychedelic drugs.Journal of psychopharmacology (Oxford, England) · 2026Review
- Cracking the Valence Code: Patterned Facial Kinematics and Neural Signatures of Emotional Expressions in Mice.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Rapid, Open-Source, and Automated Quantification of the Head Twitch Response in C57BL/6J Mice Using DeepLabCut and Simple Behavioral Analysis.ACS pharmacology & translational science · 2025Article
- Rapid, open-source, and automated quantification of the head twitch response in C57BL/6J mice using DeepLabCut and Simple Behavioral Analysis.bioRxiv : the preprint server for biology · 2025Article
- Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?Toxicology reports · 2025Review
- Article
- Sublethal Concentrations of 2C-I and 25I-NBOMe Designer Drugs ImpactInternational journal of molecular sciences · 2025Article
- Acute Effects of the Psychedelic Phenethylamine 25I-NBOMe in C57BL/6J Male Mice.International journal of molecular sciences · 2025Article
- The novel psychoactive substance 25E-NBOMe induces reward-related behaviors via dopamine D1 receptor signaling in male rodents.Archives of pharmacal research · 2024Article
- Molecular and Medical Aspects of Psychedelics.International journal of molecular sciences · 2023Review
- Identification of 5-HTNature communications · 2023Article
- Acute pharmacological profile of 2C-B-Fly-NBOMe in male Wistar rats-pharmacokinetics, effects on behaviour and thermoregulation.Frontiers in pharmacology · 2023Article
- Automated Detection of Psychedelic-Induced Head-Twitch Response in Mice.Methods in molecular biology (Clifton, N.J.) · 2023Article
- Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines.Psychopharmacology · 2023Article
4 more citing papers are in PubMed but not listed here.
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2 authors.
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Abstract
N-benzyl substitution markedly enhances the affinity of phenethylamine hallucinogens at the 5-HT(2A) receptor. N-benzyl substituted derivatives of 2,5-dimethoxy-4-iodophenethylamine (2C-I), such as N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (25I-NBOMe) and N-(2,3-methylenedioxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (25I-NBMD), have appeared recently as designer drugs, but have not been characterized behaviorally. The head twitch response (HTR) is induced by 5-HT(2A) receptor activation in rats and mice, and is widely used as a behavioral proxy for hallucinogen effects in humans. Nevertheless, it is not clear whether phenethylamine hallucinogens reliably provoke this behavior. Hence, we investigated whether 2C-I, 25I-NBOMe and 25I-NBMD induce head twitches in C57BL/6J mice. The HTR was assessed using a head-mounted magnet and a magnetometer coil. 2C-I (1-10 mg/kg SC), 25I-NBOMe (0.1-1 mg/kg SC), and 25I-NBMD (1-10 mg/kg SC) induced the HTR. 25I-NBOMe displayed 14-fold higher potency than 2C-I, and the selective 5-HT(2A) antagonist M100,907 completely blocked the HTR induced by all three compounds. These findings show that phenethylamine hallucinogens induce the HTR by activating 5-HT(2A) receptors. Our results demonstrate that 25I-NBOMe is a highly potent derivative of 2C-I, confirming previous in vitro findings that N-benzyl substitution increases 5-HT(2A) affinity. Given the high potency and ease of synthesis of N-benzylphenethylamines, it is likely that the recreational use of these hallucinogens will become more widespread in the future.
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