N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine
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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
- Weight
- Average: 312.369
Monoisotopic: 312.147392512 - Chemical Formula
- C18H20N2O3
- Synonyms
- 25CN-NBOH
- NBOH-2C-CN
Pharmacology
- Indication
Not Available
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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.
Target Actions Organism U5-hydroxytryptamine receptor 2A agonistHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when 1,2-Benzodiazepine is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine. Acenocoumarol The risk or severity of adverse effects can be increased when N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine is combined with Acenocoumarol. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine. Agomelatine The risk or severity of CNS depression can be increased when Agomelatine is combined with N-(2-hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine. - Food Interactions
- Not Available
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 32CN2DQE3Q
- 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
- 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]
- 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]
- Tolerance and Tachyphylaxis to Head Twitches Induced by the 5-HT2A Agonist 25CN-NBOH in Mice [Link]
- External Links
- ChemSpider
- 58191431
- ZINC
- ZINC000098210306
- PDBe Ligand
- U0G
- Wikipedia
- 25CN-NBOH
- PDB Entries
- 6wha
Clinical Trials
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
Property Value Source Water Solubility 0.0197 mg/mL ALOGPS logP 2.22 ALOGPS logP 1.69 Chemaxon logS -4.2 ALOGPS pKa (Strongest Acidic) 8.32 Chemaxon pKa (Strongest Basic) 10.2 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 74.51 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 89.3 m3·mol-1 Chemaxon Polarizability 34.23 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-08fr-0779000000-61703d12da3a9907bf78 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-08fu-0925000000-07821a5568a636571bd1 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0941000000-0bbff815533b40e8591e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0952000000-39fabea221fef663b1f9 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-08i3-0920000000-b7f712c0b549971b89ae Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0609-2950000000-e57e5d8cb4c3b7cdf7ba Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
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1. Details5-hydroxytryptamine receptor 2A
- 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
- 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]
- 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 at January 12, 2018 16:45 / Updated at June 12, 2020 16:53