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ChemicalBook--->CAS DataBase List--->67227-56-9

67227-56-9

67227-56-9 Structure

67227-56-9 Structure
IdentificationMore
[Name]

Fenoldopam
[CAS]

67227-56-9
[Synonyms]

6-CHLORO-2,3,4,5-TETRAHYDRO-1-(4-HYDROXYPHENYL)-1H-3-BENZAZEPINE-7,8-DIOL HYDROCHLORIDE
6-CHLORO-2,3,4,5-TETRAHYDRO-1-(4-HYDROXYPHENYL)-1H-3-BENZAZEPINE-7,8-DIOL MESYLATE
8-chloro-2-(4-hydroxyphenyl)-4-azabicyclo[5.4.0]undeca-7,9,11-triene-9,10-diol methanesulphonate
CORLOPAM MESYLATE
FENOLDOPAM
FENOLDOPAM HYDROCHLORIDE
FENOLDOPAM MESYLATE
(r)-6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1h-3-benzazepine-7,8-diol
FenoldopamMesylateBase
6-Chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benz.A~pine-7,8-diol
Corlopam
SKF-82526
SKF-82526-J
[EINECS(EC#)]

266-612-7
[Molecular Formula]

C17H20ClNO6S
[MDL Number]

MFCD04112986
[Molecular Weight]

401.86
[MOL File]

67227-56-9.mol
Chemical PropertiesBack Directory
[Boiling point ]

522.6±50.0 °C(Predicted)
[density ]

1.380±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

DMSO: >12 mg/mL
[form ]

Powder
[pka]

8.50±0.40(Predicted)
[color ]

off-white
[CAS DataBase Reference]

67227-56-9(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R22:Harmful if swallowed.
R36:Irritating to the eyes.
R42/43:May cause sensitization by inhalation and skin contact .
[Safety Statements ]

S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
[WGK Germany ]

3
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Nitromethane-->Veratraldehyde-->Isovanillin-->3,4-Dimethoxyphenethylamine-->2-(2-CHLORO-3,4-DIMETHOXYPHENYL) ETHYLAMINE-->2-Chloro-3,5-dinitrobenzoic acid-->Boron tribromide
Hazard InformationBack Directory
[Originator]

Corlopam,Pharmaforce, Inc.
[Uses]

Dopamine D1-receptor agonist. Antihypertensive.
[Uses]

dopamine receptor agonists
[Uses]

The dopamine receptors play important role in cognition, memory, learning, and motor control (1). These receptors have been implicated as a therapeutic target for many psychiatric and neurological disorders. Fenoldopam is a selective dopamine 1 receptor agonist with diuretic and properties (2,3).
[Definition]

ChEBI: Fenoldopam is a benzazepine. It has a role as a dopaminergic antagonist, a vasodilator agent, an alpha-adrenergic agonist, a dopamine agonist and an antihypertensive agent.
[Manufacturing Process]

2-Chloro-3,4-dimethoxyphenethylamine (1.0 g) was reacted with 0.70 g of pmethoxystyrene oxide to give the hydroxyphenethylamine; m.p. 118.5-121°C. This compound (2.16 g) was stirred at room temperature in 15 ml of trifluoroacetic acid with 4 drops of conc. sulfuric acid. After purification over a silica gel column with chloroform, 10% methanol/chloroform as eluates, was obtained 6-chloro-7,8-dimethoxy-1-p-methoxyphenyl-2,3,4,5-tetrahydro-1H- 3-benzazepine (0.78 g), m.p. 143-145°C.
The trimethoxy product (0.87 g, 2.50 mmoles) in 25 ml of dry methylene chloride was cooled in an ice-methanol bath and 12.5 ml (25.0 mmoles) of boron tribromide in methylene chloride was added dropwise. After stirring for 4 hours, the mixture was cooled in an ice bath while methanol was carefully added to give 0.37 g of 6-chloro-7,8-dihydroxy-1-p-hydroxyphenyl-2,3,4,5- tetrahydro-1H-3-benzazepine hydrobromide, m.p. 215°C.
The base was regenerated from the hydrobromide salt using sodium carbonate solution in 85% yield. Treating the base with various acids gave the following salts: dl-tartrate, fumarate, hydrochloride, sulfate, and the most water soluble one, the methanesulfonate, m.p. 272°C.
[Brand name]

Corlopam (Hospira).
[Therapeutic Function]

Antihypertensive
[Biological Activity]

Selective D 1 -like dopamine receptor partial agonist (EC 50 = 57 nM). Vasodilator in vivo and does not readily cross the blood-brain barrier. Also α 2 -adrenoceptor antagonist in vitro (K i = 15-25 nM).
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

67227-56-9(sigmaaldrich)
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