4-Bromo-2,5-dimethoxyphenethylamine

Identification

Name
4-Bromo-2,5-dimethoxyphenethylamine
Accession Number
DB01537
Type
Small Molecule
Groups
Experimental, Illicit
Description
Not Available
Structure
Thumb
Synonyms
  • 2C-B
External IDs
J456.895H
Product Ingredients
Not Available
Approved Prescription Products
Not Available
Approved Generic Prescription Products
Not Available
Approved Over the Counter Products
Not Available
Unapproved/Other Products
Not Available
International/Other Brands
Not Available
Brand mixtures
Not Available
Categories
UNII
V77772N32H
CAS number
66142-81-2
Weight
Average: 260.128
Monoisotopic: 259.020791344
Chemical Formula
C10H14BrNO2
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
A5-hydroxytryptamine receptor 2C
partial agonist
Human
U5-hydroxytryptamine receptor 2A
partial agonist
Human
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
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
PubChem Compound
98527
PubChem Substance
46504806
ChemSpider
88978
BindingDB
50005267
ChEBI
189669
ChEMBL
CHEMBL292821
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

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 Solubility0.199 mg/mLALOGPS
logP1.99ALOGPS
logP1.84ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)9.68ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.48 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity59.84 m3·mol-1ChemAxon
Polarizability23.54 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9947
Blood Brain Barrier+0.8982
Caco-2 permeable+0.7033
P-glycoprotein substrateNon-substrate0.6176
P-glycoprotein inhibitor INon-inhibitor0.7931
P-glycoprotein inhibitor IINon-inhibitor0.8669
Renal organic cation transporterNon-inhibitor0.5643
CYP450 2C9 substrateNon-substrate0.8869
CYP450 2D6 substrateSubstrate0.6374
CYP450 3A4 substrateSubstrate0.5337
CYP450 1A2 substrateInhibitor0.9076
CYP450 2C9 inhibitorNon-inhibitor0.8789
CYP450 2D6 inhibitorInhibitor0.5364
CYP450 2C19 inhibitorNon-inhibitor0.5363
CYP450 3A4 inhibitorNon-inhibitor0.7322
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5051
Ames testAMES toxic0.5201
CarcinogenicityNon-carcinogens0.7964
BiodegradationNot ready biodegradable0.8039
Rat acute toxicity2.5052 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6033
hERG inhibition (predictor II)Inhibitor0.65
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted LC-MS/MS Spectrum - 10V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 10V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, NegativePredicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of chemical entities known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Benzenoids
Sub Class
Benzene and substituted derivatives
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
Dimethoxybenzene / P-dimethoxybenzene / Phenethylamine / Anisole / Phenoxy compound / Phenol ether / 2-arylethylamine / Alkyl aryl ether / Bromobenzene / Halobenzene
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
2-arylethylamine (CHEBI:189669 )

Targets

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:17337633 ]
  2. 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. [PubMed:15006903 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Partial 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. 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. [PubMed:15006903 ]
  2. 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. [PubMed:17337633 ]
Drug created on July 31, 2007 07:10 / Updated on September 26, 2017 01:42