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Carvedilol
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Name

Carvedilol

 EINECS 1308068-626-2
CAS No. 72956-09-3 Density 1.25 g/cm3
PSA 75.74000 LogP 4.12890
Solubility 449.2ug/L(22.5 oC) Melting Point 113-117 °C
Formula C24H26N2O4 Boiling Point 655.2 °C at 760 mmHg
Molecular Weight 496.517 Flash Point 350.1 °C
Transport Information UN 3077 9/PG 3 Appearance colourless crystalline powder
Safety 61-36-26 Risk Codes 51/53-36/37/38-20/21/22
Molecular Structure Molecular Structure of 72956-09-3 (Carvedilol) Hazard Symbols HarmfulXn, DangerousN
Synonyms

2-Propanol, 1-(9H-carbazol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)-, (+-)-;Carvedilolum [Latin];Carvedilol [USAN:BAN:INN:JAN];Coreg (TN);Carvedilol (JAN/USAN);2-Propanol,1-(9H-carbazol-4-yloxy)-3-[[2- (2-methoxyphenoxy)ethyl]amino]-;SKF 105517;(+-)-1-(Carbazol-4-yloxy)-3-((2-(o-methoxyphenoxy)ethyl)amino)-2-propanol;DQ 2466;1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethylamino]propan-2-ol;

Article Data 46

Carvedilol Synthetic route

787598-91-8

(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol salicylate

A

918903-20-5

C39H39N3O6

B

72956-09-3

carvedilol

Conditions
ConditionsYield
With sodium hydroxide In water; isopropyl alcohol at 50 - 70℃; for 0.75h;A n/a
B 91.21%
Stage #1: (+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol salicylate With triethylamine In ethyl acetate at 10 - 35℃; for 1h;
Stage #2: With sodium chloride In water; ethyl acetate for 0.5h;
180987-80-8

5-(((9H-carbazol-4-yl)oxy)methyl)-3-(2-(2-methoxyphenoxy)ethyl)oxazolidin-2-one

72956-09-3

carvedilol

Conditions
ConditionsYield
With sodium hydroxide In propan-1-ol at 60℃; for 4h; Solvent; Temperature;89.11%
With sodium hydroxide In ethanol Reflux; Inert atmosphere;70%
With ethanol; sodium hydroxide Inert atmosphere; Reflux;70%
1016214-10-0

(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol tolsylate

72956-09-3

carvedilol

Conditions
ConditionsYield
With sodium carbonate In water; ethyl acetate Product distribution / selectivity;88%
With sodium carbonate In water; ethyl acetate80%
With sodium hydroxide; water In isopropyl alcohol Product distribution / selectivity;
72955-94-3

1-[benzyl[2(2-methoxyphenoxy)ethyl]amino]-3-(9H-carbazol-4-yloxy)propan-2-ol

72956-09-3

carvedilol

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In water; ethyl acetate at 20 - 50℃; for 8h;84%
With hydrogen; palladium 10% on activated carbon In methanol at 70℃; under 2942.29 - 4413.43 Torr;76.7%
With hydrogen; 5%-palladium/activated carbon In ethyl acetate at 60 - 70℃; under 2574.5 - 3310.08 Torr; for 10h;
143412-40-2, 143412-41-3, 72955-96-5

1-amino-3-(9H-carbazol-4-yloxy)-propan-2-ol

53815-60-4

1-(2-chloroethoxy)-2-methoxybenzene

72956-09-3

carvedilol

Conditions
ConditionsYield
With potassium carbonate In toluene at 80 - 85℃;83%
1836-62-0

2-(2-methoxy-phenoxy)-ethylamine

51997-51-4

4-(2,3-epoxypropoxy)carbazole

72956-09-3

carvedilol

Conditions
ConditionsYield
In isopropyl alcohol for 5h; Inert atmosphere; Reflux;81%
With N-ethyl-N,N-diisopropylamine In 1,2-dimethoxyethane at 80 - 85℃;36.26%
With sulfuric acid; potassium carbonate In isopropyl alcohol at 80℃; for 6h;

4-[2-(tert-butyldiphenylsilyloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propyloxy]carbazole

72956-09-3

carvedilol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 30 - 40℃; for 17h;67%
72956-09-3

(+/-) 1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethyl]amino-2-propanol oxalate

72956-09-3

carvedilol

Conditions
ConditionsYield
With ammonia In dichloromethane; water at 20℃; for 1h; pH=9.0 - 9.3;63.2%
1836-62-0

2-(2-methoxy-phenoxy)-ethylamine

51997-51-4

4-(2,3-epoxypropoxy)carbazole

A

918903-20-5

C39H39N3O6

B

72956-09-3

carvedilol

Conditions
ConditionsYield
In dimethyl sulfoxide at 68 - 72℃; for 18 - 20h;A n/a
B 58%
64464-07-9

2-[(2-methoxy)phenoxy]ethylamine hydrochloride

51997-51-4

4-(2,3-epoxypropoxy)carbazole

72956-09-3

carvedilol

Conditions
ConditionsYield
Stage #1: 2-[(2-methoxy)phenoxy]ethylamine hydrochloride With sodium hydroxide In water at 20℃; pH=9 - 9.5;
Stage #2: 4-(2,3-epoxypropoxy)carbazole In water at 80 - 85℃; for 0.75 - 1h; Product distribution / selectivity;		45.99%
Stage #1: 2-[(2-methoxy)phenoxy]ethylamine hydrochloride With sodium hydroxide In water; isopropyl alcohol at 20℃; pH=9 - 9.5;
Stage #2: 4-(2,3-epoxypropoxy)carbazole In water; isopropyl alcohol for 4 - 5h; Product distribution / selectivity; Heating / reflux;		43.05%
With potassium carbonate In i-Amyl alcohol at 80 - 85℃; for 7h;41%
With calcium carbonate In isopropyl alcohol at 80℃; for 4h;

Carvedilol Chemical Properties

Structure of Carvedilol (CAS NO.72956-09-3): 

IUPAC Name: 1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethylamino]propan-2-ol 
Empirical Formula: C24H26N2O4
Molecular Weight: 406.4742g/mol
Index of Refraction: 1.657
Molar Refractivity: 119.59 cm3
Molar Volume: 325.1 cm3
Polarizability: 47.41×10-24cm3
Surface Tension: 53.9 dyne/cm
Density: 1.25 g/cm3
Flash Point: 350.1 °C
Enthalpy of Vaporization: 101.39 kJ/mol 
Melting Point: 113-117°C
Boiling Point: 655.2 °C at 760 mmHg
Vapour Pressure: 4.63E-18 mmHg at 25°C 
Product Categories: Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals;API's;Adrenoceptor 
Canonical SMILES: COC1=CC=CC=C1OCCNCC(COC2=CC=CC3=C2C4=CC=CC=C4N3)O
InChI: InChI=1S/C24H26N2O4/c1-28-21-10-4-5-11-22(21)29-14-13-25-15-17(27)16-30-23-12-6-9-20-24(23)18-7-2-3-8-19(18)26-20/h2-12,17,25-27H,13-16H2,1H3
InChIKey: OGHNVEJMJSYVRP-UHFFFAOYSA-N

Carvedilol Uses

 Carvedilol (CAS NO.72956-09-3) is a beta blocker and an alpha blocker indicated in the treatment of mild to moderate congestive heart failure (CHF).

Carvedilol Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 1gm/kg (1000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 1181, 1989.
mouse LD50 intraperitoneal 364mg/kg (364mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA		 New Cardiovascular Drugs. Vol. 5, Pg. 135, 1987.
mouse LD50 intravenous 27mg/kg (27mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LIVER: OTHER CHANGES		 New Cardiovascular Drugs. Vol. 5, Pg. 135, 1987.
mouse LDLo oral 8gm/kg (8000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 1181, 1989.
rat LD50 intraperitoneal 769mg/kg (769mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA		 New Cardiovascular Drugs. Vol. 5, Pg. 135, 1987.
rat LD50 intravenous 25mg/kg (25mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LIVER: OTHER CHANGES		 New Cardiovascular Drugs. Vol. 5, Pg. 135, 1987.
rat LDLo oral 8gm/kg (8000mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 1181, 1989.

Carvedilol Safety Profile

Hazard Codes of Carvedilol (CAS NO.72956-09-3): DangerousN,HarmfulXn
Risk Statements: 51/53-36/37/38-20/21/22
R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R36/37/38: Irritating to eyes, respiratory system and skin. 
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 61-36-26
S61: Avoid release to the environment. Refer to special instructions / safety data sheets. 
S36: Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 3077 9/PG 3
RTECS: UA8670000

Carvedilol Specification

 Carvedilol , its cas register number is 72956-09-3. It also can be called (+-)-1-(Carbazol-4-yloxy)-3-((2-(o-
methoxyphenoxy)ethyl)amino)-2-propanol ; (+-)-1-Carbazol-4-yloxy)-3-((2-(o-methoxyphenoxy)ethyl)amino)-2-propanol ;
 2-Propanol, 1-(9H-carbazol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)-, (+-)- ; BM 14190 ; Carvedilolum ; Coreg ;
 DQ 2466 ; HSDB 7044 ; SKF 105517 ; UNII-0K47UL67F2 . Carvedilol (CAS NO.72956-09-3) is a colourless crystalline solid. Side effects of carvedilol were observed to include nightmares,sleep disturbances and anxiety and panic attacks. This is based on a single case report of a patient already diagnosed with anxiety disorder and using the drug improperly before bedtime at elevated doses.

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