Bretylium (CED0007238)

Record Information
Version1.0
Creation Date2016-05-25 18:25:39 UTC
Update Date2026-08-18 11:53:01 UTC
Accession NumberCHEM022252
Identification
Common NameBretylium
ClassSmall Molecule
Description
Bretylium is an organic compound with the formula C11H17BrN and an average molecular weight of 243.16 g/mol. Bretylium belongs to the phenylmethylamines, a subclass of benzene and substituted derivatives within the organic compounds. This compound is associated with six recorded sources, including electrical and electronic equipment such as electrically stimulated smoking devices, as well as household cleaning and consumer products like tobacco smoke filters, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Additionally, it is found in healthcare, pharmaceuticals, and veterinary products, specifically within class i and iii antiarrhythmics. Recorded exposure routes for the substance include intravenous and intramuscular administration. At the molecular level, bretylium interacts with two recorded protein targets. It acts as an antagonist or inhibitor of the beta-1 adrenergic receptor (ADRB1) and the sodium/potassium-transporting ATPase subunit alpha-1 (ATP1A1).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(2-Bromobenzyl)ethyldimethylaminiumChEBI
2-Bromo-N-ethyl-N,N-dimethylbenzenemethanaminiumChEBI
N-Ethyl-N,N-dimethyl-2-bromobenzenemethanaminiumChEBI
BretylateHMDB
Bretylium tolsylateHMDB
Bretylium tosylateHMDB
BretylumHMDB
Bretylium bromideHMDB
Bretylium chlorideHMDB
Bretylium iodideHMDB
Chemical FormulaC11H17BrN
Average Molecular Mass243.163 g/mol
Monoisotopic Mass242.054 g/mol
CAS Registry Number59-41-6
IUPAC Name[(2-bromophenyl)methyl](ethyl)dimethylazanium
Traditional Namebretylium
SMILESCC[N+](C)(C)CC1=CC=CC=C1Br
InChI IdentifierInChI=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 KeyAAQOQKQBGPPFNS-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP-1.4ALOGPS
logP-1.1ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)17.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.89 m³·mol⁻¹ChemAxon
Polarizability23.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00or-9660000000-f1a790c5dc75745515bfNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0090000000-4aeb2988fef6edbee36eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03xr-0390000000-a00c3f0ed8c3aa8c892aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-2910000000-431fec477d416b1fea58Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
250.0Log mg/kg[140:440]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
285Antiarrhythmics, class i and iiiHealthcare, pharmaceuticals & veterinary productsNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)5768.32
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)3688.11
Cholinesterase structureClick to view 3D structureCholinesteraseP06276HumansPredicted (SEA)3323.23
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)5243.53
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)5331.27
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)4854.99
Click to view 3D structurePotassium channel subfamily K member 2Q920B6Rattus norvegicusPredicted (SEA)42.1164
Click to view 3D structure5-hydroxytryptamine receptor 2BP30994Rattus norvegicusPredicted (SEA)738.945
Click to view 3D structurePhotosystem II protein D1P07753Chlamydomonas reinhardtiiPredicted (SEA)47.0988
Click to view 3D structureMuscarinic acetylcholine receptor M2P06199Sus scrofaPredicted (SEA)24.8339
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)2814.95
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP08909RatPredicted (SEA)859.767
Interferon alpha/beta receptor 1 structureClick to view 3D structureInterferon alpha/beta receptor 1P17181HumansPredicted (SEA)16.8154
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)2279.58
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)2703.24
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)2942.16
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)3265.46
Click to view 3D structureNeuronal acetylcholine receptor subunit alpha-7P22770Gallus gallusPredicted (SEA)44.5298
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)4937.51
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)2876.06
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)3846.76
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)3469.43
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)3439.61
Trace amine-associated receptor 1 structureClick to view 3D structureTrace amine-associated receptor 1Q96RJ0HumansPredicted (SEA)1027.53
Click to view 3D structureProtein arginine N-methyltransferase 1Q63009Rattus norvegicusPredicted (SEA)13.2344
Concentrations
Not Available
External Links
DrugBank IDDB01158
HMDB IDHMDB0015289
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBretylium
Chemspider ID2337
ChEBI ID3172
PubChem Compound ID2431
Kegg Compound IDC06855
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References