Fenoldopam

Fenoldopam
  • CAS No.:67227-56-9
Other grades of this product :
Fenoldopam Basic information
Product Name:Fenoldopam
Synonyms:(r)-6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1h-3-benzazepine-7,8-diol;Corlopam;SKF-82526;SKF-82526-J;CORLOPAM MESYLATE;FENOLDOPAM;FENOLDOPAM HYDROCHLORIDE;FenoldopamMesylateBase
CAS:67227-56-9
MF:C16H16ClNO3
MW:305.76
EINECS:266-612-7
Product Categories:Agonists;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals;API
Mol File:67227-56-9.mol
Fenoldopam Chemical Properties
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
pka8.50±0.40(Predicted)
color off-white
CAS DataBase Reference67227-56-9(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 22-36-42/43
Safety Statements 22-26-36/37/39
WGK Germany 3
MSDS Information
Fenoldopam Usage And Synthesis
OriginatorCorlopam,Pharmaforce, Inc.
UsesDopamine D1-receptor agonist. Antihypertensive.
Usesdopamine receptor agonists
UsesThe 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).
Manufacturing Process2-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 nameCorlopam (Hospira).
Therapeutic FunctionAntihypertensive
Biological ActivitySelective 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).

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