Ifenprodil Chemical Properties

Melting point:

114°

Boiling point:

463.62°C (rough estimate)

Density 

1.0825 (rough estimate)

refractive index 

1.5614 (estimate)

storage temp. 

Store at RT

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.99±0.26(Predicted)

color 

White to Off-White

Water Solubility 

Soluble to 15 mM in water with gentle warming

Safety Information

Toxicity

LD50 oral in mouse: 320mg/kg

Ifenprodil Usage And Synthesis

Originator

Vadilex,Carriere,France,1972

Uses

Ifenprodil is a NMDA receptor antagonist.

Uses

vasodilator

Definition

ChEBI: 4-[1-hydroxy-2-[4-(phenylmethyl)-1-piperidinyl]propyl]phenol is a member of piperidines.

Manufacturing Process

The initial steps involve reacting benzyl chloride with 4- hydroxypropiophenone. The benzyloxypropiophene thus obtained is first brominated and then reacted with 4-benzylpiperidine to give 1-(pbenzyloxyphenyl)-2-(4-benzyl-piperidino)propan-1-one.
The neutral tartrate may be prepared directly by reduction of 1-(pbenzyloxyphenyl)-2-(4-benzyl-piperidino)propan-1-one. For the reduction, a mixture of 175 g of ketone (0.425 mol) and 32 g of tartaric acid (0.213 mol) is hydrogenated at 50°C under pressure of 50 kg/cm2 in 440 ml of methanol in the presence of 12 g of palladium on charcoal.
The catalyst is filtered off at elevated temperature, and the filtrate is concentrated by evaporation under reduced pressure to a volume of 300 ml and added in a thin stream to 2.5 liters of diethyl ether with mechanical agitation. The precipitate is separated, washed with diethyl ether and dried in vacuo at 80° to 85°C for several hours. 325 g (96% yield) of the neutral tartrate of 1-(p-hydroxyphenyl)-2-(4-benzyl-piperidino)propan-1-ol are obtained.

Therapeutic Function

Vasodilator

Biological Activity

NMDA receptor antagonist, acting at the polyamine site. Also an α -adrenergic vasodilator. σ 2 ligand displaying about 3-fold selectivity over σ 1 sites.

Ifenprodil(23210-56-2)Related Product Information

• Benzyl chloride
• Diltiazem
• Fasudil hydrochloride
• CHLOROPHOSPHONAZO III
• Propyl gallate
• Benzyltriethylammonium chloride
• Haloperidol
• Diphenylsilanediol
• Buflomedil hydrochloride
• Prostaglandin E1
• 6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil
• 1-Propanol
• 3-Aminophenol
• Propyl butyrate
• Phenol Red
• Phenol
• IFENPRODIL TARTRATE SALT,IFENPRODIL TARTARATE,IFENPRODIL HEMITARTRATE,Ifenprodil L-(+)-Tartrate,IFENPRODIL TARTRATE
• Diphenoxylate