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Propafenone hydrochloride
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Name

Propafenone hydrochloride

 EINECS 251-867-9
CAS No. 34183-22-7 Density N/A
PSA 58.56000 LogP 4.43430
Solubility N/A Melting Point 165-167 °C
Formula C21H28ClNO3 Boiling Point 519.6 °C at 760 mmHg
Molecular Weight 377.911 Flash Point 268 °C
Transport Information N/A Appearance White solid
Safety 53-36/37/39-45 Risk Codes 46-22
Molecular Structure Molecular Structure of 34183-22-7 (1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenylpropan-1-one hydrochloride) Hazard Symbols ToxicT, HarmfulXn
Synonyms

1-Propanone,1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenyl-, hydrochloride (9CI);Propiophenone, 2'-[2-hydroxy-3-(propylamino)propoxy]-3-phenyl-, hydrochloride(8CI);Arythmol;Pronon;Rythmol;Rytmonorm;

Article Data 3

Propafenone hydrochloride Synthetic route

107-10-8

propylamine

22525-95-7

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

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

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
1214-47-7

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

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

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
3516-95-8

2'-hydroxy-3-phenylpropiophenone

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
16619-51-5

2'-allyloxychalcone

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
34183-22-7

propafenone hydrochloride

18162-48-6

tert-butyldimethylsilyl chloride

C27H41NO3Si

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

propafenone hydrochloride

530-62-1

1,1'-carbonyldiimidazole

C22H25NO4

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 50℃; for 12h;68%

copper(II) choride dihydrate

34183-22-7

propafenone hydrochloride

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%
34183-22-7

propafenone hydrochloride

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%

Propafenone hydrochloride Specification

The Propafenone hydrochloride is an organic compound with the formula C21H28ClNO3. The IUPAC name of this chemical is 1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenylpropan-1-one hydrochloride. With the CAS registry number 34183-22-7, it is also named as 1-propanone, 1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenyl-, hydrochloride. The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals; Sodium channel. Besides, it should be stored in a closed place at temperature of 2 - 8 °C. It have been shown to increase the occurrence of arrhythmias, primarily in patients with underlying heart disease.

Physical properties about Propafenone hydrochloride are: (1)CD/LogP: 3.93; (2)ACD/LogD (pH 5.5): 0.9; (3)ACD/LogD (pH 7.4): 1.97; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 6.25; (6)ACD/KOC (pH 5.5): 3.04; (7)ACD/KOC (pH 7.4): 35.75; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 12; (11)Polar Surface Area: 38.77 Å2; (12)Flash Point: 268 °C; (13)Enthalpy of Vaporization: 83.42 kJ/mol; (14)Boiling Point: 519.6 °C at 760 mmHg; (15)Vapour Pressure: 1.27E-11 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. Besides, this chemical may cause heritable genetic damage. When you are using it, wear suitable gloves and eye/face protection and avoid exposure - obtain special instructions before use. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: Cl.O=C(c1ccccc1OCC(O)CNCCC)CCc2ccccc2
(2)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
(3)InChIKey: XWIHRGFIPXWGEF-UHFFFAOYAM
(4)Std. InChI: InChI=1S/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
(5)Std. InChIKey: XWIHRGFIPXWGEF-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 60mg/kg (60mg/kg)   Cardiac Arrhythmias: Diagnosis, Prognosis, Therapy; Proceedings International Rytmonorm- Congress. Vol. 1, Pg. 103, 1983.
child TDLo oral 133mg/kg (133mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: CHANGE IN CONDUCTION VELOCITY		 Annals of Emergency Medicine. Vol. 16, Pg. 437, 1987.
dog LD50 intravenous 10mg/kg (10mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 1849, 1976.
mammal (species unspecified) LD50 subcutaneous 200mg/kg (200mg/kg)   Ceska a Slovenska Farmacie. Vol. 47, Pg. 179, 1998.
man LDLo oral 4286ug/kg/15H (4.286mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP Postgraduate Medical Journal. Vol. 60, Pg. 155, 1984.
man TDLo oral 53571ug/kg (53.571mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

GASTROINTESTINAL: OTHER CHANGES		 Deutsche Medizinische Wochenschrift. Vol. 116, Pg. 1573, 1991.
man TDLo oral 2346mg/kg/1Y- (2346mg/kg) PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE Mayo Clinic Proceedings. Vol. 70, Pg. 469, 1995.
mouse LD50 intraperitoneal 79mg/kg (79mg/kg)   Drugs in Japan Vol. -, Pg. 1035, 1990.
mouse LD50 intravenous 25mg/kg (25mg/kg)   Drugs in Japan Vol. -, Pg. 1035, 1990.
mouse LD50 oral 341mg/kg (341mg/kg)   Drugs in Japan Vol. -, Pg. 1035, 1990.
mouse LD50 subcutaneous 100mg/kg (100mg/kg)   Drugs in Japan Vol. -, Pg. 1035, 1990.
rat LD50 intraperitoneal 59mg/kg (59mg/kg)   Drugs in Japan Vol. -, Pg. 1035, 1990.
rat LD50 intravenous 18800ug/kg (18.8mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 1849, 1976.
rat LD50 oral 700mg/kg (700mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 1849, 1976.
rat LD50 subcutaneous 156mg/kg (156mg/kg)   Drugs in Japan Vol. -, Pg. 1035, 1990.
women TDLo oral 12mg/kg/1D-I (12mg/kg) PERIPHERAL NERVE AND SENSATION: PARESTHESIS

BEHAVIORAL: WAKEFULNESS

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"		 Journal of Clinical Psychiatry. Vol. 46, Pg. 104, 1985.

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