BRETYLIUM TOSYLATE

Product Name: BRETYLIUM TOSYLATE
CAS No.: 61-75-6
Chemical Name: BRETYLIUM TOSYLATE
Synonyms: ornid;asl-603;darentin;bretylan;bretylol;bretylate;darenthin;esulfonicacid;ulfonicacid(1:1);BretyliuM p-Tolu
CBNumber: CB5239348
Molecular Formula: C18H24BrNO3S
Formula Weight: 414.36
MOL File: 61-75-6.mol

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BRETYLIUM TOSYLATE Property

Melting point:: 97-99°
storage temp.: Inert atmosphere,Room Temperature
solubility: H2O: soluble50mg/mL
form: Solid
color: white
InChIKey: KVWNWTZZBKCOPM-UHFFFAOYSA-M

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22
Safety Statements: 36
RTECS: BO9450000
HS Code: 2923900100
Toxicity: LD50 in mice (mg/kg): 400 orally; 250 i.m. (Goldenthal)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 1076352
Product name: Bretylium tosylate
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 200mg
Price: $483
Updated: 2024/03/01

Cayman Chemical

Product number: 29979
Product name: Bretylium (tosylate)
Packaging: 10mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 29979
Product name: Bretylium (tosylate)
Packaging: 250mg
Price: $456
Updated: 2024/03/01

Cayman Chemical

Product number: 29979
Product name: Bretylium (tosylate)
Packaging: 50mg
Price: $139
Updated: 2024/03/01

Cayman Chemical

Product number: 29979
Product name: Bretylium (tosylate)
Packaging: 100mg
Price: $243
Updated: 2024/03/01

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BRETYLIUM TOSYLATE Chemical Properties,Usage,Production

Chemical Properties

White Solid

Originator

Bretylate,Wellcome,UK,1973

Uses

Bretylium 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.

Definition

ChEBI: 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 fibril ation.

Manufacturing Process

N-o-Bromobenzyl-N,N-dimethylamine (100g) and ethyl p-toluenesulfonate (94 g) were mixed and warmed to 50°-60°C; after standing for either (a) a minimum of 96 hours at 15°-20°C or (b) a minimum of 18 hours at 50°-60°C and cooling to room temperature, a hard, crystalline mass was formed. Recrystallization of this product from acetone (2.0 ml/g of crude solid), followed by filtration and drying to 60°C gave N-o-bromobenzyl-N-ethyl-N,Ndimethylammonium p-toluenesulfonate as a white, crystalline solid, MP 97°- 99°C. For this procedure it was necessary that the reactants were substantially colorless and of a high purity.

brand name

Bretylol (Mayne).

Therapeutic Function

Adrenergic blocker; Antiarrhythmic

General Description

Bretylium 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.

Biological Activity

Bretylium tosylate has a biphasic response, initially inducing norepinephrine release followed by sympathetic ganglionic blockade; class III antiarrhythmic agent; competitive inhibitor of acetylcholinesterase.

Clinical Use

Currently, bretylium is reserved for use in ventriculararrhythmias that are resistant to other therapy. Bretyliumdoes not suppress phase 4 depolarization, a common actionof other antiarrhythmic agents. It prolongs the effectiverefractory period relative to the action potential durationbut does not affect conduction time and is categorized asa class III antiarrhythmic agent. Because bretylium doesnot have properties similar to those of the other antiarrhythmicagents, it has been suggested that its action is aresult of its adrenergic neuronal-blocking properties; theantiarrhythmic properties of the drug, however, are notaffected by administration of reserpine. Bretylium is also alocal anesthetic, but it has not been possible to demonstratesuch an effect on atria of experimental animals, except atvery high concentrations. Therefore, the precise mechanismof the antiarrhythmic action of bretylium remains tobe resolved.

Side effects

The major adverse effect associated with bretylium tosylate is hypotension, including orthostatic hypotension, which may be very severe.

BRETYLIUM TOSYLATE Preparation Products And Raw materials

Raw materials

o-Toluidine N,N-Dimethylbenzylamine 2-Bromobenzyl bromide 2-Bromotoluene Methyl bromide

Preparation Products

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BRETYLIUM TOSYLATE Suppliers

Canada 1 China 61 Germany 2 India 4 Ireland 1 Switzerland 1 United Kingdom 5 United States 26 Global 101

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61-75-6, BRETYLIUM TOSYLATERelated Search:

RIMANTADINE HCL USP(CRM STANDARD) 4-Fluorobenzyl bromide 2-Nitrobenzyl bromide Ethambutol Acebutolol Benzyltrimethylammonium hydroxide 2-BROMOBENZYLAMINE (2-BROMOBENZYL)METHYLAMINE 2-bromo-N,N-dimethylbenzylamine p-Toluenesulfonic acid BRETYLIUM TOSYLATE TETRAMETHYLAMMONIUM P-TOLUENESULFONATE

(o-bromobenzyl)ethyldimethyl-ammoniup-toluenesulfonate

2-bromo-n-ethyl-n,n-dimethylbenzenemethanaminium4-methylbenzenesulfonate

2-bromo-n-ethyl-n,n-dimethyl-benzenemethanaminiusaltwith4-methylbenzen

darentin

dimethylethyl-o-bromobenzylammonium-p-toluenesulphonate

esulfonicacid

n-ethyl-n-o-bromobenzyl-n,n-dimethylammoniumtosylate

ornid

ulfonicacid(1:1)

Bretylium Tosylate (200 mg)

BretyliuM p-Tolu

N-(2-BroMobenzyl)-N,N-diMethylethanaMiniuM 4-Methylbenzenesulfonate

BretyliuM Tosylate USP

2-bromo-n-ethyl-n,n-dimethyl-benzenemethanaminiusaltwith4-methylbenzenes

asl-603

bretylan

bretylate

bretyliump-toluenesulfonate

Bretyliumtosilate

bretylol

darenthin

[O-BROMOBENZYL]ETHYLDIMETHYL-AMMONIUM P-TOLUENESULFONATE

BRETYLIUM TOSYLATE

BRETYLIUM TOSYLATE ADRENERGIC NEURON BLO

BRETYLIUM TOSYLATE, PHARMA

(2-Bromobenzyl)ethyldimethylammonium p-toluenesulfonate

Bretyliume tosylate

Retylium tosylate

(2-bromobenzyl)-ethyl-dimethyl-ammonium

(2-bromophenyl)methyl-ethyl-dimethylazanium

(2-bromophenyl)methyl-ethyl-dimethyl-azanium

2-bromo-n-ethyl-n,n-dimethylbenzenemethanaminium

BRETYLIUM TOSYLATE USP/EP/BP

Bretylium Tosylate (1076352)

inhibit,Inhibitor,Bretylium,Bretylium tosylate

Bretylium tosylate, 10 mM in DMSO

61-75-6

C18H24BrNO3S

C18H24BO3RnS

C11H17BrNC7H7O3S

Amines

Aromatics

Intermediates & Fine Chemicals

Pharmaceuticals

Sulfur & Selenium Compounds