N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine
Accession Number
DB13948
Type
Small Molecule
Groups
Experimental
Description

25CN-NBOH (N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine) is a newly developed selective 5-HT2A agonist. It has been tested with regard to the head-twitch-response (HTR) model of 5-HT2A activity and effects on locomotion 3. It was discovered in 2014 at the University of Copenhagen.

Structure
Thumb
Synonyms
  • 25CN-NBOH
  • NBOH-2C-CN
Categories
UNII
Not Available
CAS number
1391489-32-9
Weight
Average: 312.369
Monoisotopic: 312.147392512
Chemical Formula
C18H20N2O3
InChI Key
VWEDZTZAXHMZIL-UHFFFAOYSA-N
InChI
InChI=1S/C18H20N2O3/c1-22-17-10-15(11-19)18(23-2)9-13(17)7-8-20-12-14-5-3-4-6-16(14)21/h3-6,9-10,20-21H,7-8,12H2,1-2H3
IUPAC Name
4-(2-{[(2-hydroxyphenyl)methyl]amino}ethyl)-2,5-dimethoxybenzonitrile
SMILES
COC1=CC(C#N)=C(OC)C=C1CCNCC1=C(O)C=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action

25CN-NBOH is one of the most selective agonist ligands for the 5-HT2A receptor discovered. It has a pKi of 8.88 at the human 5-HT2A receptor and is 100x more selective for 5-HT2A over 5-HT2C, and 46x more selective for 5-HT2A over 5-HT2B 1,2.

TargetActionsOrganism
U5-hydroxytryptamine receptor 2A
agonist
Humans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
Not Available

References

General References
  1. Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Brauner-Osborne H, Kristensen JL: Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chem Neurosci. 2014 Mar 19;5(3):243-9. doi: 10.1021/cn400216u. Epub 2014 Jan 15. [PubMed:24397362]
  2. Jensen AA, McCorvy JD, Leth-Petersen S, Bundgaard C, Liebscher G, Kenakin TP, Brauner-Osborne H, Kehler J, Kristensen JL: 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. J Pharmacol Exp Ther. 2017 Jun;361(3):441-453. doi: 10.1124/jpet.117.239905. Epub 2017 Mar 30. [PubMed:28360333]
  3. Tolerance and Tachyphylaxis to Head Twitches Induced by the 5-HT2A Agonist 25CN-NBOH in Mice [Link]
External Links
ChemSpider
58191431
Wikipedia
25CN-NBOH

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0197 mg/mLALOGPS
logP2.22ALOGPS
logP1.69ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.32ChemAxon
pKa (Strongest Basic)10.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.51 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity89.3 m3·mol-1ChemAxon
Polarizability34.23 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Brauner-Osborne H, Kristensen JL: Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chem Neurosci. 2014 Mar 19;5(3):243-9. doi: 10.1021/cn400216u. Epub 2014 Jan 15. [PubMed:24397362]
  2. Jensen AA, McCorvy JD, Leth-Petersen S, Bundgaard C, Liebscher G, Kenakin TP, Brauner-Osborne H, Kehler J, Kristensen JL: 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. J Pharmacol Exp Ther. 2017 Jun;361(3):441-453. doi: 10.1124/jpet.117.239905. Epub 2017 Mar 30. [PubMed:28360333]

Drug created on January 12, 2018 09:45 / Updated on May 09, 2019 00:20