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

pka

8.50±0.40(Predicted)

form 

Powder

color 

off-white

CAS DataBase Reference

67227-56-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-42/43

Safety Statements 

22-26-36/37/39

WGK Germany 

3

Fenoldopam Usage And Synthesis

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).

Fenoldopam(67227-56-9)Related Product Information

• Propylene glycol
• Estradiol
• Estramustine
• 2,2-Dimethyl-1,3-propanediol
• Polyethylene Glycol
• Triton X-100
• Ethylene glycol
• Difluorochloromethane
• Fenoldopam intermediate
• Fenoldopam mesylate
• INTERMEDIATE OF FENOLDOPAM
• FENOLDOPAM MONOHYDROBROMIDE
• Fenoldopam
• N-[2-HYDROXY-2-(4-METHOXYPHENYL)ETHYL]-2-(2-CHLORO-3,4-DIMETHOXYPHENYL)ETHYLAMINE(FOR FENOLDOPAM)
• Fenoldopam 8-sulfate
• 2-chloro-3,4-dimethoxy benzaldehyde (intermediate of fenoldopam)
• FENOLDOPAM RELATED COMPOUND B (20 MG) (1 H-3-BENZAZAPINE-7,8-DIOL, 2,3,4,5-TETRAHYDRO-1 -(4-HYDROXYPHENYL)-, METHANESULFONATE)
• FENOLDOPAM MESYLATE USP(CRM STANDARD)