Identification
- Generic Name
- 4-Bromo-2,5-dimethoxyphenethylamine
- DrugBank Accession Number
- DB01537
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
Structure for 4-Bromo-2,5-dimethoxyphenethylamine (DB01537)
- Weight
- Average: 260.128
Monoisotopic: 259.020791344 - Chemical Formula
- C10H14BrNO2
- Synonyms
- 2C-B
- External IDs
- J456.895H
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism A5-hydroxytryptamine receptor 2C partial agonistHumans U5-hydroxytryptamine receptor 2A partial 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 softwareAcebutolol The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Acebutolol. Alfuzosin The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Alfuzosin. Amitriptyline The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Amitriptyline. Amitriptylinoxide The risk or severity of hypertension can be increased when Amitriptylinoxide is combined with 4-Bromo-2,5-dimethoxyphenethylamine. Amoxapine The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Amoxapine. Aripiprazole The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Aripiprazole. Aripiprazole lauroxil The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Aripiprazole lauroxil. Asenapine The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Asenapine. Atenolol The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Atenolol. Benzylpenicilloyl polylysine 4-Bromo-2,5-dimethoxyphenethylamine may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Methoxybenzenes
- Direct Parent
- Dimethoxybenzenes
- Alternative Parents
- Phenethylamines / Phenoxy compounds / Anisoles / 2-arylethylamines / Bromobenzenes / Aralkylamines / Alkyl aryl ethers / Aryl bromides / Organopnictogen compounds / Organobromides show 2 more
- Substituents
- 2-arylethylamine / Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic homomonocyclic compound / Aryl bromide / Aryl halide / Bromobenzene / Dimethoxybenzene show 16 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- 2-arylethylamine (CHEBI:189669)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- V77772N32H
- CAS number
- 66142-81-2
- InChI Key
- YMHOBZXQZVXHBM-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H14BrNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3
- IUPAC Name
- 2-(4-bromo-2,5-dimethoxyphenyl)ethan-1-amine
- SMILES
- COC1=CC(Br)=C(OC)C=C1CCN
References
- General References
- Not Available
- External Links
- PubChem Compound
- 98527
- PubChem Substance
- 46504806
- ChemSpider
- 88978
- BindingDB
- 50005267
- ChEBI
- 189669
- ChEMBL
- CHEMBL292821
- ZINC
- ZINC000002564752
- Wikipedia
- 4-Bromo-2,5-dimethoxyphenethylamine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Not Yet Recruiting Basic Science Healthy Subjects (HS) 1
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 0.199 mg/mL ALOGPS logP 1.99 ALOGPS logP 1.84 Chemaxon logS -3.1 ALOGPS pKa (Strongest Basic) 9.68 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 44.48 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 59.84 m3·mol-1 Chemaxon Polarizability 23.54 Å3 Chemaxon Number of Rings 1 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
Property Value Probability Human Intestinal Absorption + 0.9947 Blood Brain Barrier + 0.8982 Caco-2 permeable + 0.7033 P-glycoprotein substrate Non-substrate 0.6176 P-glycoprotein inhibitor I Non-inhibitor 0.7931 P-glycoprotein inhibitor II Non-inhibitor 0.8669 Renal organic cation transporter Non-inhibitor 0.5643 CYP450 2C9 substrate Non-substrate 0.8869 CYP450 2D6 substrate Substrate 0.6374 CYP450 3A4 substrate Substrate 0.5337 CYP450 1A2 substrate Inhibitor 0.9076 CYP450 2C9 inhibitor Non-inhibitor 0.8789 CYP450 2D6 inhibitor Inhibitor 0.5364 CYP450 2C19 inhibitor Non-inhibitor 0.5363 CYP450 3A4 inhibitor Non-inhibitor 0.7322 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5051 Ames test AMES toxic 0.5201 Carcinogenicity Non-carcinogens 0.7964 Biodegradation Not ready biodegradable 0.8039 Rat acute toxicity 2.5052 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6033 hERG inhibition (predictor II) Inhibitor 0.65
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Partial agonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
- Gene Name
- HTR2C
- Uniprot ID
- P28335
- Uniprot Name
- 5-hydroxytryptamine receptor 2C
- Molecular Weight
- 51820.705 Da
References
- Moya PR, Berg KA, Gutierrez-Hernandez MA, Saez-Briones P, Reyes-Parada M, Cassels BK, Clarke WP: Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J Pharmacol Exp Ther. 2007 Jun;321(3):1054-61. Epub 2007 Mar 2. [Article]
- Villalobos CA, Bull P, Saez P, Cassels BK, Huidobro-Toro JP: 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A receptor antagonists in Xenopus laevis oocytes. Br J Pharmacol. 2004 Apr;141(7):1167-74. Epub 2004 Mar 8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Partial agonist
- Curator comments
- Studies demonstrate 2C-B is a low efficacy serotonin 5-HT2A receptor partial agonist or even full antagonist.
- 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
- Villalobos CA, Bull P, Saez P, Cassels BK, Huidobro-Toro JP: 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A receptor antagonists in Xenopus laevis oocytes. Br J Pharmacol. 2004 Apr;141(7):1167-74. Epub 2004 Mar 8. [Article]
- Moya PR, Berg KA, Gutierrez-Hernandez MA, Saez-Briones P, Reyes-Parada M, Cassels BK, Clarke WP: Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J Pharmacol Exp Ther. 2007 Jun;321(3):1054-61. Epub 2007 Mar 2. [Article]
Drug created at July 31, 2007 13:10 / Updated at June 12, 2020 16:51