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Name |
Amiodarone |
EINECS | 217-772-1 |
CAS No. | 1951-25-3 | Density | 1.581 g/cm3 |
PSA | 42.68000 | LogP | 6.93620 |
Solubility | 716.4mg/L(25 oC) | Melting Point |
156oC |
Formula | C25H29I2NO3 | Boiling Point | 635.073 °C at 760 mmHg |
Molecular Weight | 645.319 | Flash Point | 337.88 °C |
Transport Information | N/A | Appearance | N/A |
Safety | 36 | Risk Codes | 20/21/22 |
Molecular Structure | Hazard Symbols | Xn | |
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; |
Article Data | 3 |
2-chloro-N,N-diethylethylamine hydrochloride
2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran
Amiodarone
Conditions | Yield |
---|---|
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 12h; | 91% |
2-n-butyl 3-(4-methoxy benzoyl)-benzofuran
Amiodarone
Conditions | Yield |
---|---|
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 |
1-(4-methoxyphenyl)-1,3-heptanedione
Amiodarone
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane; water for 5h; |
tetrafluoroboric acid diethyl ether
Amiodarone
Conditions | Yield |
---|---|
With 2,3,7,8-tetrafluorothianthrene; trifluoroacetic anhydride In acetonitrile at 0 - 25℃; regioselective reaction; | 92% |
Conditions | Yield |
---|---|
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% |
Amiodarone
di-tert-butyl chloromethyl phosphate
Conditions | Yield |
---|---|
With 1,2,2,6,6-pentamethylpiperidine; sodium iodide In acetonitrile at 40℃; for 24h; | 48% |
Amiodarone
Conditions | Yield |
---|---|
in vivo metabolism (human); | |
With carbonochloridic acid 1-chloro-ethyl ester In toluene for 16h; Heating; | |
With human liver microsomes Kinetics; Concentration; Reagent/catalyst; |
DOT Classification: 3; Label: Flammable Liquid
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. |