ContaminantDB: Bretylium

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:25:39 UTC

Update Date

2016-11-09 01:17:27 UTC

Accession Number

CHEM022252

Identification

Common Name

Bretylium

Class

Small Molecule

Description

Bretylium blocks the release of noradrenaline from the peripheral sympathetic nervous system, and is used in emergency medicine, cardiology, and other specialties for the acute management of ventricular tachycardia and ventricular fibrillation. The primary mode of action for bretylium is thought to be inhibition of voltage-gated K(+) channels. Recent evidence has shown that bretylium may also inhibit the Na,K-ATPase by binding to the extracellular K-site.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2-Bromobenzyl)ethyldimethylaminium	ChEBI
2-Bromo-N-ethyl-N,N-dimethylbenzenemethanaminium	ChEBI
N-Ethyl-N,N-dimethyl-2-bromobenzenemethanaminium	ChEBI
Bretylate	HMDB
Bretylium tolsylate	HMDB
Bretylium tosylate	HMDB
Bretylum	HMDB
Bretylium bromide	HMDB
Bretylium chloride	HMDB
Bretylium iodide	HMDB

Chemical Formula

C₁₁H₁₇BrN

Average Molecular Mass

243.163 g/mol

Monoisotopic Mass

242.054 g/mol

CAS Registry Number

59-41-6

IUPAC Name

[(2-bromophenyl)methyl](ethyl)dimethylazanium

Traditional Name

bretylium

SMILES

CC[N+](C)(C)CC1=CC=CC=C1Br

InChI Identifier

InChI=1S/C11H17BrN/c1-4-13(2,3)9-10-7-5-6-8-11(10)12/h5-8H,4,9H2,1-3H3/q+1

InChI Key

AAQOQKQBGPPFNS-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylmethylamines

Alternative Parents

Substituents

Benzylamine
Phenylmethylamine
Aralkylamine
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Tetraalkylammonium salt
Quaternary ammonium salt
Amine
Organic nitrogen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Organic salt
Hydrocarbon derivative
Organopnictogen compound
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:3172 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.1	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	17.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.89 m³·mol⁻¹	ChemAxon
Polarizability	23.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00or-9660000000-f1a790c5dc75745515bf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-4aeb2988fef6edbee36e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03xr-0390000000-a00c3f0ed8c3aa8c892a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-2910000000-431fec477d416b1fea58	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01158

HMDB ID

HMDB0015289

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Bretylium (CHEM022252)

Structure for CHEM022252: Bretylium