The selective 5-HT2A receptor agonist 25CN-NBOH: structure-activity relationship, in vivo pharmacology, and in vitro and ex vivo binding characteristics of [3H]25CN-NBOH.

@article{Jensen2020TheS5,
  title={The selective 5-HT2A receptor agonist 25CN-NBOH: structure-activity relationship, in vivo pharmacology, and in vitro and ex vivo binding characteristics of [3H]25CN-NBOH.},
  author={Anders A. Jensen and Adam L. Halberstadt and Emil M{\"a}rcher-R{\o}rsted and Anna U Odland and Muhammad Rafique Chatha and Nikolaj Raahauge Speth and Gudrun Liebscher and Martin Hansen and Hans Br{\"a}uner‐Osborne and Mikael Palner and Jesper T. Andreasen and Jesper L. Kristensen},
  journal={Biochemical pharmacology},
  year={2020},
  pages={
          113979
        }
}
View on PubMed
doi.org
7 Citations
Background Citations
1
Methods Citations
1

7 Citations

Citation Type

Citation Type

Investigating the role of 5-HT2A and 5-HT2C receptor activation in the effects of psilocybin, DOI, and citalopram on marble burying in mice
25CN‐NBOH: A Selective Agonist for in vitro and in vivo Investigations of the Serotonin 2A Receptor
TLDR
25CN‐NBOH has been used to investigate the effects of selective 5‐HT2AR activation in vivo, and has thus become an important pharmacological tool for the exploration of 5‐ HT2AR signaling in a range of animal models.
A quantitative method for the selective 5-HT2A agonist 25CN-NBOH in rat plasma and brain.
Acute serotonin 2A receptor activation impairs behavioral flexibility in mice
Design, Synthesis, and Pharmacological Characterization of Heterobivalent Ligands for the Putative 5-HT2A/mGlu2 Receptor Complex.
TLDR
While functional crosstalk between 5-HT2A and mGlu2 was demonstrated, it remains unclear how these heterobivalent ligands interact with the putative receptor complex.
Molecular and Functional Imaging Studies of Psychedelic Drug Action in Animals and Humans
TLDR
There remains considerable scope for basic imaging research on the sites of interaction of hallucinogens and their cerebrometabolic effects; it is expected that hybrid imaging with PET in conjunction with functional magnetic resonance imaging (fMRI) should provide especially useful for the next phase of this research.
Improving cognitive functioning in major depressive disorder with psychedelics: A dimensional approach

References

SHOWING 1-10 OF 71 REFERENCES
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
TLDR
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.
Support for 5-HT2C receptor functional selectivity in vivo utilizing structurally diverse, selective 5-HT2C receptor ligands and the 2,5-dimethoxy-4-iodoamphetamine elicited head-twitch response model
Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors
TLDR
The present study examined and compared the binding of 17 phenylisopropylamines at human 5- HT2A, 5-HT2B, and 5-Hat2C receptors and found a significant correlation between 5-ht2B receptor affinity and human hallucinogenic potency.
Interaction of 5-HT2A and 5-HT2C Receptors in R(−)-2,5-Dimethoxy-4-iodoamphetamine-Elicited Head Twitch Behavior in Mice
TLDR
Results of these experiments provide strong evidence that DOI-elicited head-twitch behavior is a 5-HT2A agonist-mediated effect, with subsequent inhibition of head- twitch behavior being driven by competing 5- HT2C agonist activity.
Contribution of a helix 5 locus to selectivity of hallucinogenic and nonhallucinogenic ligands for the human 5-hydroxytryptamine2A and 5-hydroxytryptamine2C receptors: direct and indirect effects on ligand affinity mediated by the same locus.
TLDR
The molecular basis of ligand selectivity of hallucinogenic and nonhallucinogenic compounds of varying structural classes for the human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors was investigated with the use of reciprocal site-directed mutagenesis.
Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists.
TLDR
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.
Pharmacological and behavioral characterization of the 5-HT2A receptor in C57BL/6N mice
TLDR
The current chronic agonist treatment study demonstrated an important similarity between the 5-HT2A receptor in mice, rats, and rabbits, while antagonist treatment revealed an interesting difference from previous studies in rabbits.
5-HT2A and 5-HT2C receptors exert opposing effects on locomotor activity in mice
TLDR
Data indicate that the decrease in locomotor activity induced by 10 mg/kg DOI is mediated by 5-HT2C receptors, an interpretation that is supported by the finding that the selective 5- HT2C agonist WAY 161,503 produces reductions in the locomotory activity that are potentiated in 5HT2A KO mice.
The 5-hydroxytryptamine 2A receptor agonists DOI and 25CN-NBOH decrease marble burying and reverse 8-OH-DPAT-induced deficit in spontaneous alternation
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
TLDR
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.
...
...