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34183-22-7

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34183-22-7 Usage

Description

Propafenone hydrochloride is a class I anti-arrhythmic agent with basic local anaesthetic and membrane-stabilizing properties. Some P-adrenergic blocking action has also been described. Propafenone decreases the depolarization velocity and slows conduction in the His-Purkinje system with resultant increase in the PR interval and the QRS complex. Propafenone is used in the treatment of paroxysmal supraventricular tachycardias and ventricular arrhythmias.Propafenone should not be used in uncontrolled cardiac failure, severe obstructive pulmonary disease or marked hypotension. Propafenone may worsen myasthenia gravis.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 34183-22-7 differently. You can refer to the following data:
1. Propafenone hydrochloride is a class IC antiarrhythmic agent used for the management of severe ventricular and supraventricular arrhythmias. It has beta-blocking and weak calcium channel blocking properties, as well as some negative inotropic activity. Propafenone is in a class of medications called antiarrhythmics. It works by acting on the heart muscle to improve the heart's rhythm.
2. Sodium channel blocker. Antiarrhythmic (class IC)

Definition

ChEBI: Propafenone hydrochloride is a hydrochloride that is the monohydrochloride salt of propafenone. It is a class 1C antiarrhythmic drug with local anesthetic effects, and is used in the management of supraventricular and ventricular arrhythmias. It has a role as an anti-arrhythmia drug. It contains a propafenone(1+).

Brand name

Rythmol (Reliant).

Pharmacokinetics

Propafenone hydrochloride (Rythmol(R)) is similar in action to flecainide. It reduces the fast inward sodium current in Purkinje fibres and to a lesser extent in myocardial fibres. Unlike other class l drugs, propafenone has mild B-blocking effects. This may contribute to its overall effects on the conduction system. lt is also believed to have calcium channel-blocking effects, which may contribute to its mild negative inotropic effects.

Clinical Use

Anti-arrhythmic agent: Ventricular arrhythmias Paroxysmal supraventricular tachyarrhythmias, (including paroxysmal atrial flutter or fibrillation, and paroxysmal re-entrant tachycardias involving the AV node or accessory pathway) where standard therapy has failed or is unsuitable

Drug interactions

Potentially hazardous interactions with other drugs Anti-arrhythmics: increased myocardial depression with other anti-arrhythmics. Antibacterials: increased metabolism with rifampicin (reduced effect). Anticoagulants: enhanced anticoagulant effect of coumarins. Antidepressants: increased risk of arrhythmias with tricyclics; metabolism of propafenone possibly inhibited by paroxetine (increased risk of toxicity). Antihistamines: increased risk of ventricular arrhythmias with mizolastine - avoid. Antipsychotics: increased risk of ventricular arrhythmias with antipsychotics that prolong the QT interval. Antivirals: concentration of propafenone increased by saquinavir and ritonavir and possibly by fosamprenavir, increased risk of ventricular arrhythmias - avoid; use with caution with telaprevir. Beta-blockers: increased myocardial depression; increased concentration of metoprolol and propranolol. Cardiac glycosides: increased digoxin concentration - halve digoxin dose. Ciclosporin: possibly increased ciclosporin concentration. Ulcer-healing drugs: levels increased by cimetidine.

Metabolism

Propafenone is hepatically metabolised mainly by CYP2D6 isoenzyme but also to a small extent by CYP1A2 and CYP3A4. This forms 2 active metabolites, 5-hydroxypropafenone and N-depropylpropafenone and some inactive ones. Propafenone and its metabolites also undergo glucuronidation. The extent of metabolism is genetically determined. Propafenone is excreted in the urine and faeces mainly in the form of conjugated metabolites.

Check Digit Verification of cas no

The CAS Registry Mumber 34183-22-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,4,1,8 and 3 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 34183-22:
(7*3)+(6*4)+(5*1)+(4*8)+(3*3)+(2*2)+(1*2)=97
97 % 10 = 7
So 34183-22-7 is a valid CAS Registry Number.
InChI:InChI=1/C21H27NO3.ClH/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17;/h3-11,18,22-23H,2,12-16H2,1H3;1H

34183-22-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (P2301)  Propafenone Hydrochloride  >98.0%(HPLC)(T)

  • 34183-22-7

  • 1g

  • 690.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000455)  Propafenone hydrochloride  European Pharmacopoeia (EP) Reference Standard

  • 34183-22-7

  • Y0000455

  • 1,880.19CNY

  • Detail
  • Sigma

  • (P4670)  Propafenone hydrochloride  

  • 34183-22-7

  • P4670-5G

  • 1,193.40CNY

  • Detail
  • USP

  • (1570304)  Propafenone hydrochloride  United States Pharmacopeia (USP) Reference Standard

  • 34183-22-7

  • 1570304-200MG

  • 4,662.45CNY

  • Detail

34183-22-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name propafenone hydrochloride

1.2 Other means of identification

Product number -
Other names 1-[2-(2-Hydroxy-3-(propylamino)propoxy)phenyl]-3-phenyl-1-propanone hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:34183-22-7 SDS

34183-22-7Synthetic route

propylamine
107-10-8

propylamine

1-(2-(oxiran-2-ylmethoxy)phenyl)-3-phenylpropan-1-one
22525-95-7

1-(2-(oxiran-2-ylmethoxy)phenyl)-3-phenylpropan-1-one

propafenone hydrochloride
34183-22-7

propafenone hydrochloride

Conditions
ConditionsYield
Stage #1: propylamine; 1-(2-(oxiran-2-ylmethoxy)phenyl)-3-phenylpropan-1-one for 4h; Reflux;
Stage #2: With hydrogenchloride In water for 1h; Reflux;
85%
Stage #1: propylamine; 1-(2-(oxiran-2-ylmethoxy)phenyl)-3-phenylpropan-1-one at 20 - 50℃; for 6h;
Stage #2: With hydrogenchloride for 1h; Reflux;
74.5%
2'-hydroxydihydrochalcone sodium

2'-hydroxydihydrochalcone sodium

propafenone hydrochloride
34183-22-7

propafenone hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 8 h / 110 °C
2.1: 6 h / 20 - 50 °C
2.2: 1 h / Reflux
View Scheme
1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
1214-47-7

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

propafenone hydrochloride
34183-22-7

propafenone hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 2-Phenylbenzothiazolin; aluminum (III) chloride / toluene / 2 h / 110 °C
1.2: 6 h / 20 - 25 °C
2.1: 8 h / 110 °C
3.1: 6 h / 20 - 50 °C
3.2: 1 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: tris(pentafluorophenyl)borate; triethylsilane; 1,1,1,3',3',3'-hexafluoro-propanol / 1 h / 40 °C
2.1: 4 h / Reflux
3.1: 4 h / Reflux
3.2: 1 h / Reflux
View Scheme
1-(2-(allyloxy)phenyl)-3-phenylpropan-1-one

1-(2-(allyloxy)phenyl)-3-phenylpropan-1-one

propafenone hydrochloride
34183-22-7

propafenone hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 48 h / 20 °C
2.1: 4 h / Reflux
2.2: 1 h / Reflux
View Scheme
2'-hydroxy-3-phenylpropiophenone
3516-95-8

2'-hydroxy-3-phenylpropiophenone

propafenone hydrochloride
34183-22-7

propafenone hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 4 h / Reflux
2.1: 4 h / Reflux
2.2: 1 h / Reflux
View Scheme
2'-allyloxychalcone
16619-51-5

2'-allyloxychalcone

propafenone hydrochloride
34183-22-7

propafenone hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tris(pentafluorophenyl)borate; triethylsilane; 1,1,1,3',3',3'-hexafluoro-propanol / 1 h / 40 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 48 h / 20 °C
3.1: 4 h / Reflux
3.2: 1 h / Reflux
View Scheme
propafenone hydrochloride
34183-22-7

propafenone hydrochloride

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

C27H41NO3Si

C27H41NO3Si

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 0 - 22℃; for 12h; Inert atmosphere;83%
propafenone hydrochloride
34183-22-7

propafenone hydrochloride

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

C22H25NO4

C22H25NO4

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 50℃; for 12h;68%
copper(II) choride dihydrate

copper(II) choride dihydrate

propafenone hydrochloride
34183-22-7

propafenone hydrochloride

[(1-[2-[2-oxy-3-(propylamino)propoxy]phenyl]-3-phenyl-1-propanone(1-))2 (copper(II))2 (chloride)2]
907997-08-4

[(1-[2-[2-oxy-3-(propylamino)propoxy]phenyl]-3-phenyl-1-propanone(1-))2 (copper(II))2 (chloride)2]

Conditions
ConditionsYield
With NaOH In methanol at room temp., methanolic soln. of hydrochloride of the ligand mixed with soln. of CuCl2*2H2O in the same solvent (ratio 1:1), dropwise additionof NaOH; pptn., crystals filtered, washed with methanol, dried over P2O5; elem. anal.;60%
propafenone hydrochloride
34183-22-7

propafenone hydrochloride

C21H25(2)H2NO3

C21H25(2)H2NO3

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine; tris(pentafluorophenyl)borate; water-d2 In tetrahydrofuran at 100℃; for 12h; Inert atmosphere; regioselective reaction;46%
copper(II) choride dihydrate

copper(II) choride dihydrate

propafenone hydrochloride
34183-22-7

propafenone hydrochloride

trans-N-[(1-[2-[2-oxy-3-(propylamino)propoxy]phenyl]-3-phenyl-1-propanone(1-))2 copper(II)]
907997-07-3

trans-N-[(1-[2-[2-oxy-3-(propylamino)propoxy]phenyl]-3-phenyl-1-propanone(1-))2 copper(II)]

Conditions
ConditionsYield
With NaOH In methanol at room temp. CuCl2*2H2O in MeOH added to the hydrochloride of the ligand in the same solvent (ratio 1:10), dropwise addition of NaOH; pptn. of crystals after 5 d, crystals filtered, washed with methanol, recrystallized from ethanol, dried over P2O5; elem. anal.;35%
propafenone hydrochloride
34183-22-7

propafenone hydrochloride

uridine 5'-diphosphoglucuronic acid triammonium salt

uridine 5'-diphosphoglucuronic acid triammonium salt

Propafenone glucuronide

Propafenone glucuronide

Conditions
ConditionsYield
With mercaptoethyl alcohol; sepharose bound UDP-glucuronyltransferase; magnesium chloride In ethanol at 37℃; for 4h; Product distribution; Tris-HCl buffer; pH and concentrations varied; enzyme activity;
With mercaptoethyl alcohol; magnesium chloride In ethanol at 37℃; for 4h; Sepharose bound UDP-glucuronyltransferase, Tris-HCl buffer pH 7.5; Yield given;
propafenone hydrochloride
34183-22-7

propafenone hydrochloride

C40H51NO3Si

C40H51NO3Si

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0 - 22 °C / Inert atmosphere
2: triethylamine / acetonitrile / 12 h / 0 - 22 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: 1H-imidazole / dichloromethane / 12 h / 0 - 22 °C / Inert atmosphere
2: triethylamine / acetonitrile / 12 h / 0 - 22 °C / Inert atmosphere
View Scheme
propafenone hydrochloride
34183-22-7

propafenone hydrochloride

C40H47(2)H4NO3Si

C40H47(2)H4NO3Si

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 22 °C / Inert atmosphere
2: triethylamine / acetonitrile / 12 h / 0 - 22 °C / Inert atmosphere
3: [(2)H6]acetone; tris(pentafluorophenyl)borate / toluene / 3 h / 150 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: 1H-imidazole / dichloromethane / 12 h / 0 - 22 °C / Inert atmosphere
2: triethylamine / acetonitrile / 12 h / 0 - 22 °C / Inert atmosphere
3: [(2)H6]acetone; tris(pentafluorophenyl)borate / toluene / 3 h / 150 °C / Inert atmosphere
View Scheme
t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

propafenone hydrochloride
34183-22-7

propafenone hydrochloride

C27H41NO3Si

C27H41NO3Si

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 22℃; Inert atmosphere;

34183-22-7Relevant articles and documents

Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- And α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol

Zhan, Xiao-Yu,Zhang, Hua,Dong, Yu,Yang, Jian,He, Shuai,Shi, Zhi-Chuan,Tang, Lei,Wang, Ji-Yu

, p. 6578 - 6592 (2020/07/17)

The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process.

Preparation of propafenone

-

, (2008/06/13)

A process for the preparation of propafenone wherein 1. 2'-hydroxyacetophenone is reacted with epichlorohydrin, 2. the resulting 2-(2',3'-epoxypropoxy)-acetophenone is reacted with propylamine, 3. the resulting 2-(2'-hydroxy-3'-propylaminopropoxy)-acetophenone is reacted with benzaldehyde, accompanied by elimination of water, and 4. the resulting 2-(2'-hydroxy-3'-propylaminopropoxy)-benzalacetophenone is hydrogenated.

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