25CN‐NBOH: A Selective Agonist for in vitro and in vivo Investigations of the Serotonin 2A Receptor

  title={25CN‐NBOH: A Selective Agonist for in vitro and in vivo Investigations of the Serotonin 2A Receptor},
  author={Emil M{\"a}rcher R{\o}rsted and Anders A. Jensen and Jesper L. Kristensen},
4‐(2‐((2‐hydroxybenzyl)amino)ethyl)‐2,5‐dimethoxybenzonitrile (25CN‐NBOH) was first reported as a potent and selective serotonin 2A receptor (5‐HT2AR) agonist in 2014, and it has since found extensive use as a pharmacological tool in a variety of in vitro, ex vivo and in vivo studies. 25CN‐NBOH is readily available from a synthetic perspective using standard chemical transformations, and displays favorable physiochemical properties in terms of stability and solubility. Due to its superior… 


Detailed Characterization of the In Vitro Pharmacological and Pharmacokinetic Properties of N-(2-Hydroxybenzyl)-2,5-Dimethoxy-4-Cyanophenylethylamine (25CN-NBOH), a Highly Selective and Brain-Penetrant 5-HT2A Receptor Agonist
25CN-NBOH appears to be a superior selective and brain-penetrant 5-HT2A receptor agonist compared with (±)-2,5-dimethoxy-4-iodoamphetamine (DOI), and it is proposed that the compound could be a valuable tool for future investigations of physiologic functions mediated by this receptor.
Correlating the Metabolic Stability of Psychedelic 5-HT2A Agonists with Anecdotal Reports of Human Oral Bioavailability
It is hypothesized that the low hepatic stability of the N-benzylated phenethylamines renders them orally inactive due to first pass metabolism, which is supported by anecdotal data from recreational use of these compounds.
Characterization of the hepatic cytochrome P450 enzymes involved in the metabolism of 25I-NBOMe and 25I-NBOH.
The major CYP enzymes involved in the metabolism of 25I-NBOMe and 25INBOH were identified as CYP3A4 and CYP2D6, respectively.
In vitro autoradiography of serotonin 5‐HT2A/2C receptor‐activated G protein: Guanosine‐5′‐(γ‐[35S]thio)triphosphate binding in rat brain
Autoradiography revealed a similar localization of DOI‐ and 5‐HT‐stimulated binding of [35S]GTPγS in distinct areas of prefrontal and parietal cortex, consistent with previously reported 5‐ HT2A receptor distribution.
Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists.
A series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule are prepared to determine the effects on receptor binding affinity and functional activity at 5- HT2A and 5-HT2C receptors.
A case of 25I-NBOMe (25-I) intoxication: a new potent 5-HT2A agonist designer drug
A case of self-reported exposure to 25-I (25I-NBOMe), a novel phenethylamine derivative, with subsequent quantification in serum is described, a potent new synthetic drug with apparent significant behavioral toxicity that can be detected and quantified in serum.