Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists

Research output: Contribution to journalJournal articleResearchpeer-review

Standard

Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. / Hansen, Martin; Phonekeo, Karina; Paine, James S; Leth-Petersen, Sebastian; Begtrup, Mikael; Bräuner-Osborne, Hans; Kristensen, Jesper Langgaard.

In: A C S Chemical Neuroscience, Vol. 5, No. 3, 07.01.2014, p. 243-249.

Research output: Contribution to journalJournal articleResearchpeer-review

Harvard

Hansen, M, Phonekeo, K, Paine, JS, Leth-Petersen, S, Begtrup, M, Bräuner-Osborne, H & Kristensen, JL 2014, 'Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists' A C S Chemical Neuroscience, vol. 5, no. 3, pp. 243-249. https://doi.org/10.1021/cn400216u

APA

Hansen, M., Phonekeo, K., Paine, J. S., Leth-Petersen, S., Begtrup, M., Bräuner-Osborne, H., & Kristensen, J. L. (2014). Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. A C S Chemical Neuroscience, 5(3), 243-249. https://doi.org/10.1021/cn400216u

Vancouver

Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H et al. Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. A C S Chemical Neuroscience. 2014 Jan 7;5(3):243-249. https://doi.org/10.1021/cn400216u

Author

Hansen, Martin ; Phonekeo, Karina ; Paine, James S ; Leth-Petersen, Sebastian ; Begtrup, Mikael ; Bräuner-Osborne, Hans ; Kristensen, Jesper Langgaard. / Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. In: A C S Chemical Neuroscience. 2014 ; Vol. 5, No. 3. pp. 243-249.

Bibtex

@article{7f6afab3c4824643b59108ac6c41036f,
title = "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists",
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 sub-nanomolar 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.",
author = "Martin Hansen and Karina Phonekeo and Paine, {James S} and Sebastian Leth-Petersen and Mikael Begtrup and Hans Br{\"a}uner-Osborne and Kristensen, {Jesper Langgaard}",
year = "2014",
month = "1",
day = "7",
doi = "10.1021/cn400216u",
language = "English",
volume = "5",
pages = "243--249",
journal = "A C S Chemical Neuroscience",
issn = "1948-7193",
publisher = "American Chemical Society",
number = "3",

}

RIS

TY - JOUR

T1 - Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists

AU - Hansen, Martin

AU - Phonekeo, Karina

AU - Paine, James S

AU - Leth-Petersen, Sebastian

AU - Begtrup, Mikael

AU - Bräuner-Osborne, Hans

AU - Kristensen, Jesper Langgaard

PY - 2014/1/7

Y1 - 2014/1/7

N2 - 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 sub-nanomolar 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.

AB - 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 sub-nanomolar 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.

U2 - 10.1021/cn400216u

DO - 10.1021/cn400216u

M3 - Journal article

VL - 5

SP - 243

EP - 249

JO - A C S Chemical Neuroscience

JF - A C S Chemical Neuroscience

SN - 1948-7193

IS - 3

ER -

ID: 103038300