NAV

4-Bromo-2,5-dimethoxyphenethylamine

Identification

Generic Name
4-Bromo-2,5-dimethoxyphenethylamine
DrugBank Accession Number
DB01537
Background

Not Available

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 260.128
Monoisotopic: 259.020791344
Chemical Formula
C10H14BrNO2
Synonyms
  • 2C-B
External IDs
  • J456.895H
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
A5-hydroxytryptamine receptor 2C
partial agonist
Humans
U5-hydroxytryptamine receptor 2A
partial 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
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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
Integrate drug-drug
interactions in your software
AcebutololThe therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Acebutolol.
AlfuzosinThe therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Alfuzosin.
AmitriptylineThe therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Amitriptyline.
AmitriptylinoxideThe risk or severity of hypertension can be increased when Amitriptylinoxide is combined with 4-Bromo-2,5-dimethoxyphenethylamine.
AmoxapineThe therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Amoxapine.
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
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
PhaseStatusPurposeConditionsCount
1RecruitingBasic ScienceHealthy Volunteers (HV)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
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-MSsplash10-001i-9160000000-4feb0ead4ea05d10dc70
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-0090000000-7562e9d4757f5e86d928
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1090000000-770852496a4e53d02d85
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-7290000000-973e76993a8918e34293
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-c296c3e6db197ffcfee9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9160000000-9d189a2701e698d62853
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-3690000000-2d32f6adbea59303a3c0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-140.21103
predicted
DeepCCS 1.0 (2019)
[M+H]+142.56903
predicted
DeepCCS 1.0 (2019)
[M+Na]+150.48117
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 5-hydroxytryptamine receptor 2C
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
  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. [Article]
  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. [Article]
Details2. 5-hydroxytryptamine receptor 2A
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
  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. [Article]
  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. [Article]

Drug created at July 31, 2007 13:10 / Updated at June 12, 2020 16:51