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

Generic Name
N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine
DrugBank Accession Number
DB13948
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 312.369
Monoisotopic: 312.147392512
Chemical Formula
C18H20N2O3
Synonyms
  • 25CN-NBOH
  • NBOH-2C-CN

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
AcenocoumarolThe risk or severity of adverse effects can be increased when N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
AclidiniumN-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
1391489-32-9
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

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. [Article]
  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. [Article]
  3. Tolerance and Tachyphylaxis to Head Twitches Induced by the 5-HT2A Agonist 25CN-NBOH in Mice [Link]
ChemSpider
58191431
ZINC
ZINC000098210306
PDBe Ligand
U0G
Wikipedia
25CN-NBOH
PDB Entries
6wha

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Targets

Drugtargets2
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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. [Article]
  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. [Article]

Drug created on January 12, 2018 16:45 / Updated on June 12, 2020 16:53