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1951-25-3

Basic Information
CAS No.: 1951-25-3
Name: Amiodarone
Article Data: 3
Molecular Structure:
Molecular Structure of 1951-25-3 (Amiodarone)
Formula: C25H29I2NO3
Molecular Weight: 645.319
Synonyms: Ketone,2-butyl-3-benzofuranyl 4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl (7CI,8CI);2-Butyl-3-[3,5-diiodo-4-(2-diethylaminoethoxy)benzoyl]benzofuran;2-Butyl-3-benzofuranyl p-[(2-diethylamino)ethoxy]-m,m-diiodophenyl ketone;2-n-Butyl-3',5'-diiodo-4'-N-diethylaminoethoxy-3-benzoylbenzofuran;Sedacoron;Sedacorone;
EINECS: 217-772-1
Density: 1.581 g/cm3
Melting Point: 156oC
Boiling Point: 635.073 °C at 760 mmHg
Flash Point: 337.88 °C
Solubility: 716.4mg/L(25 oC)
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22
Safety: 36
PSA: 42.68000
LogP: 6.93620
Synthetic route
869-24-9

2-chloro-N,N-diethylethylamine hydrochloride

1951-26-4

2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran

1951-25-3

Amiodarone

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 12h;91%
83790-87-8

2-n-butyl 3-(4-methoxy benzoyl)-benzofuran

1951-25-3

Amiodarone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: boron tribromide / dichloromethane
2: sodium hydroxide; iodine / methanol / 3 h / 0 - 20 °C
3: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 12 h / 20 °C
View Scheme
1137261-90-5

1-(4-methoxyphenyl)-1,3-heptanedione

1951-25-3

Amiodarone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-Bromosuccinimide; aluminum (III) chloride / nitromethane / 6 h / 80 °C
2: boron tribromide / dichloromethane
3: sodium hydroxide; iodine / methanol / 3 h / 0 - 20 °C
4: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 12 h / 20 °C
View Scheme
100-06-1

1-(4-methoxyphenyl)ethanone

1951-25-3

Amiodarone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hydride / mineral oil; tetrahydrofuran / Reflux
2: N-Bromosuccinimide; aluminum (III) chloride / nitromethane / 6 h / 80 °C
3: boron tribromide / dichloromethane
4: sodium hydroxide; iodine / methanol / 3 h / 0 - 20 °C
5: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 12 h / 20 °C
View Scheme
624-24-8

methyl valerate

1951-25-3

Amiodarone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hydride / mineral oil; tetrahydrofuran / Reflux
2: N-Bromosuccinimide; aluminum (III) chloride / nitromethane / 6 h / 80 °C
3: boron tribromide / dichloromethane
4: sodium hydroxide; iodine / methanol / 3 h / 0 - 20 °C
5: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 12 h / 20 °C
View Scheme

amiodarone decahydrochloride

1951-25-3

Amiodarone

Conditions
ConditionsYield
With potassium carbonate In dichloromethane; water for 5h;
67969-82-8

tetrafluoroboric acid diethyl ether

1951-25-3

Amiodarone

2,3,7,8-tetrafluorothianthrene-S-oxide

C37H32F4I2NO3S2(1+)*2BF4(1-)*H(1+)

Conditions
ConditionsYield
With 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride In acetonitrile at 0 - 25℃; regioselective reaction;92%
67969-82-8

tetrafluoroboric acid diethyl ether

13755-29-8

sodium tetrafluoroborate

1951-25-3

Amiodarone

2,3,7,8-tetrafluorothianthrene-S-oxide

C37H32F4I2NO3S2(1+)*BF4(1-)

Conditions
ConditionsYield
Stage #1: tetrafluoroboric acid diethyl ether; Amiodarone; 2,3,7,8-tetrafluorothianthrene-S-oxide With trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 3h; Sealed tube;
Stage #2: sodium tetrafluoroborate In dichloromethane; water
92%
1951-25-3

Amiodarone

229625-50-7

di-tert-butyl chloromethyl phosphate

di-tert-butyl N-(phosphonooxymethyl)amiodaronium chloride

Conditions
ConditionsYield
With 1,2,2,6,6-pentamethylpiperidine; sodium iodide In acetonitrile at 40℃; for 24h;48%
1951-25-3

Amiodarone

desethylamiodarone

Conditions
ConditionsYield
in vivo metabolism (human);
With carbonochloridic acid 1-chloro-ethyl ester In toluene for 16h; Heating;
With human liver microsomes Kinetics; Concentration; Reagent/catalyst;
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    Specification: EP 5 CAS RN.: 1951-25-3 EINECS: 217-772-1 Molecular Weight:

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  • Methanone,(2-butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]-

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    1951-25-3

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Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

Specification

The Amiodarone, with the CAS registry number 1951-25-3, is also known as 2-Butyl-3-benzofuranyl-4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl ketone. It belongs to the classification codes of Anti-arrhythmia Agents; Cardiac depressant [anti-arrhythmic, ventricular]; Cardiovascular Agents; Drug / Therapeutic Agent; Enzyme Inhibitors; Human Data; Vasodilator Agents. Its EINECS registry number is 217-772-1. This chemical's molecular formula is C25H29I2NO3 and molecular weight is 645.31. What's more, both its IUPAC name and systematic name are the same which is called (2-Butyl-1-benzofuran-3-yl)-[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone. Amiodarone is an antiarrhythmic agent used for various types of cardiac dysrhythmias, both ventricular and atrial. Despite relatively common side-effects, it is used in arrhythmias that are otherwise difficult to treat with medication. When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health. It is harmful by inhalation, in contact with skin and if swallowed.

Physical properties about Amiodarone are: (1)ACD/LogP: 7.815; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 4.78; (4)ACD/LogD (pH 7.4): 5.87; (5)ACD/BCF (pH 5.5): 475.19; (6)ACD/BCF (pH 7.4): 5787.95; (7)ACD/KOC (pH 5.5): 394.32; (8)ACD/KOC (pH 7.4): 4802.97; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 11; (12)Polar Surface Area: 42.68 ?2; (13)Index of Refraction: 1.625; (14)Molar Refractivity: 144.381 cm3; (15)Molar Volume: 408.224 cm3; (16)Polarizability: 57.237×10-24cm3; (17)Surface Tension: 47.799 dyne/cm; (18)Density: 1.581 g/cm3; (19)Flash Point: 337.88 °C; (20)Enthalpy of Vaporization: 93.852 kJ/mol; (21)Boiling Point: 635.073 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: Ic1cc(cc(I)c1OCCN(CC)CC)C(=O)c2c3ccccc3oc2CCCC
(2) InChI: InChI=1S/C25H29I2NO3/c1-4-7-11-22-23(18-10-8-9-12-21(18)31-22)24(29)17-15-19(26)25(20(27)16-17)30-14-13-28(5-2)6-3/h8-10,12,15-16H,4-7,11,13-14H2,1-3H3
(3) InChIKey: IYIKLHRQXLHMJQ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 568mg/kg/9W-I (568mg/kg) CARDIAC: PULSE RATE

LIVER: FATTY LIVER DEGERATION
Journal of Pediatrics. Vol. 107, Pg. 967, 1985.
man LDLo oral 1869mg/kg/22W (1869mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

ENDOCRINE: EVIDENCE OF THYROID HYPOFUNCTION

BEHAVIORAL: COMA
American Journal of Medicine. Vol. 77, Pg. 751, 1984.
man LDLo oral 2086mg/kg/2Y- (2086mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LIVER: LIVER FUNCTION TESTS IMPAIRED
Netherlands Journal of Medicine. Vol. 29, Pg. 303, 1986.
man LDLo unreported 3650mg/kg/3.5 (3650mg/kg) LIVER: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

ENDOCRINE: OTHER CHANGES
Clinical Endocrinology Vol. 45, Pg. 365, 1996.
man TDLo intravenous 4286ug/kg (4.286mg/kg) BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE Critical Care Medicine. Vol. 13, Pg. 688, 1985.
man TDLo intravenous 26mg/kg/1D-C (26mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
American Heart Journal. Vol. 131, Pg. 1214, 1996.
man TDLo oral 60mg/kg/2W-I (60mg/kg) LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: CHANGES IN OTHER CELL COUNT (UNSPECIFIED)
Chest. Vol. 88, Pg. 630, 1985.
man TDLo oral 133mg/kg/23D- (133mg/kg) SKIN AND APPENDAGES (SKIN): PHOTOSENSITIVITY: AFTER SYSTEMIC EXPOSURE Lancet. Vol. 1, Pg. 51, 1984.
man TDLo oral 390mg/kg/39W- (390mg/kg) ENDOCRINE: EVIDENCE OF THYROID HYPERFUNCTION

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI
Netherlands Journal of Medicine. Vol. 42, Pg. 21, 1993.
man TDLo oral 1714mg/kg/21W (1714mg/kg) LUNGS, THORAX, OR RESPIRATION: COUGH

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
New England Journal of Medicine. Vol. 308, Pg. 779, 1983.
man TDLo oral 3651mg/kg/2.3 (3651mg/kg) LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"

LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: MULTIPLE EFFECTS
American Journal of Gastroenterology. Vol. 83, Pg. 161, 1988.
man TDLo unreported 51mg/kg/6D-C (51mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 296, Pg. 1322, 1988.
man TDLo unreported 57mg/kg/5D-I (57mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP Annals of Internal Medicine. Vol. 97, Pg. 561, 1982.
mouse LD50 intraperitoneal 254mg/kg (254mg/kg)   European Journal of Toxicology and Environmental Hygiene. Vol. 8, Pg. 122, 1975.
mouse LD50 intravenous 178mg/kg (178mg/kg)   European Journal of Toxicology and Environmental Hygiene. Vol. 8, Pg. 188, 1975.
mouse LD50 oral > 4gm/kg (4000mg/kg)   European Patent Application. Vol. #0076973,
rat LD50 intraperitoneal 885mg/kg (885mg/kg)   European Patent Application. Vol. #0076973,
women TDLo intravenous 3mg/kg (3mg/kg) BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE Critical Care Medicine. Vol. 13, Pg. 688, 1985.
women TDLo intravenous 36mg/kg/1D-I (36mg/kg) ENDOCRINE: EVIDENCE OF THYROID HYPERFUNCTION Israel Journal of Medical Sciences. Vol. 21, Pg. 165, 1985.
women TDLo multiple routes 1475mg/kg/7W- (1475mg/kg) CARDIAC: OTHER CHANGES American Journal of Cardiology. Vol. 58, Pg. 1110, 1986.
women TDLo oral 64mg/kg/4D-I (64mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Lancet. Vol. 350, Pg. 1300, 1997.
women TDLo oral 416mg/kg/30D- (416mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Archives of Internal Medicine. Vol. 147, Pg. 50, 1987.
women TDLo oral 5200mg/kg/5Y- (5200mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ANOREXIA (HUMAN
Respiration. Vol. 49, Pg. 157, 1986.
women TDLo oral 5796mg/kg/69W (5796mg/kg) MUSCULOSKELETAL: OTHER CHANGES

ENDOCRINE: OTHER CHANGES
Italian Journal of Neurological Sciences. Vol. 8, Pg. 605, 1987.
women TDLo unreported 48mg/kg/3D-I (48mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP American Heart Journal. Vol. 130, Pg. 399, 1995.