Basic information
- CAS
61-75-6- Standard SMILES
CC[N+](C)(C)Cc1ccccc1Br.Cc1ccc(S(=O)(=O)[O-])cc1- InChIKey
KVWNWTZZBKCOPM-UHFFFAOYSA-M- Molecular formula
- C18H24BrNO3S
- Average molar mass
- 414.4 g/mol
- Monoisotopic mass
- 413.06603
Overview
Bretylium tosylate is the tosylate salt of bretylium. It blocks noradrenaline release 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. It has a role as an antihypertensive agent, an adrenergic antagonist and an anti-arrhythmia drug. It is a quaternary ammonium salt and an organosulfonate salt. It contains a bretylium.
Names & identifiers
- Preferred name
- Bretylium Tosylate
- IUPAC
- (2-bromophenyl)methyl-ethyl-dimethylazanium;4-methylbenzenesulfonate
- English name
- BRETYLIUM TOSYLATE
- Molecular formula
- C18H24BrNO3S
- Molecular weight
- 414.36
Names & synonyms
Bretylium tosylate61-75-6BretylolBretylium tosilateDarentinTosilato de bretilioTosilate de bretyliumBretylii tosilasASL-603(o-Bromobenzyl)ethyldimethylammonium p-toluenesulfonateBretilio tosilatoDTXSID1022685
Show more names
ornidbretylanbretylatedarenthinesulfonicacidulfonicacid(1:1)BretyliuM p-Tolu
Bretylium Tosylate In Dextrose 5%NSC-621642-Bromo-N-ethyl-N,N-dimethylbenzenemethanaminium 4-methylbenzenesulfonateDimethylethyl-o-bromobenzylammonium-p-toluenesulphonateN-Ethyl-N-o-bromobenzyl-N,N-dimethylammonium tosylate78ZP3YR353Benzenemethanaminium, 2-bromo-N-ethyl-N,N-dimethyl-, salt with 4-methylbenzenesulfonic acid (1:1)CHEBI:3173
Database identifiers
- CAS
61-75-6- PubChem CID
- 6100
- DTXSID
DTXSID1022685- ChEMBL
CHEMBL1095292- ChEBI
Properties
Computed structural properties
- Topological polar surface area
- 65.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 349
Experimental & physicochemical properties
Solubility>62.2 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section140.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 97 · 97-99°
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 2 O: · H2O: soluble50mg/mL
- form
- Solid
- color
- white
- Major Application
- pharmaceutical (small molecule)
- InChI
- 1S/C11H17BrN.C7H8O3S/c1-4-13(2,3)9-10-7-5-6-8-11(10)12;1-6-2-4-7(5-3-6)11(8,9)10/h5-8H,4,9H2,1-3H3;2-5H,1H3,(H,8,9,10)/q+1;/p-1
- InChIKey
- KVWNWTZZBKCOPM-UHFFFAOYSA-M
- SMILES
- Cc1ccc(cc1)S([O-])(=O)=O.CC[N+](C)(C)Cc2ccccc2Br
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - Benzenemethanaminium, 2-bromo-N-ethyl-N,N-dimethyl-, salt with 4-methylbenzenesulfonic acid (1:1): Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- WGK 3
- rtecs
- BO9450000
- hs_code
- 2923900100
- Toxicity
- LD50 in mice (mg/kg): 400 orally; 250 i.m. (Goldenthal)
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312+H332
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
MeSH Pharmacological Classification
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Drugs that bind to but do not activate ADRENERGIC RECEPTORS. Adrenergic antagonists block the actions of the endogenous adrenergic transmitters EPINEPHRINE and NOREPINEPHRINE.
Applications
UsesBretylium tosylate has a biphasic response, initially inducing norepinephrine release followed by sympathetic ganglionic blockade. Bretylium tosylate is a class III antiarrhythmic agent and a competitive inhibitor of acetylcholinesterase.
General DescriptionBretylium tosylate, (o-bromobenzyl)ethyl dimethylammonium p-toluenesulfonate(Bretylol), is an extremely bitter, white, crystalline powder.The chemical is freely soluble in water and alcohol.Bretylium tosylate is an adrenergic neuronal-blockingagent that accumulates selectively in the neurons anddisplaces norepinephrine. Because of this property,bretylium was used initially, under the trade name ofDarenthin, as an antihypertensive agent. It caused posturaldecrease in arterial pressure. This use was discontinuedbecause of the rapid development of tolerance, erratic oralabsorption of the quaternary ammonium compound, andpersistent pain in the parotid gland on prolonged therapy.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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