Ifenprodil Struktur

Ifenprodil

Bezeichnung:Ifenprodil

Englisch Name:Ifenprodil

CBNumberCB3427239

SummenformelC21H27NO2

Molgewicht325.45

Synonyma

Ifenprodil

Ifenprodil physikalisch-chemischer Eigenschaften

Schmelzpunkt	114°
Siedepunkt	463.62°C (rough estimate)
Dichte	1.0825 (rough estimate)
Brechungsindex	1.5614 (estimate)
storage temp.	Store at RT
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	9.99±0.26(Predicted)
Farbe	White to Off-White
Wasserlöslichkeit	Soluble to 15 mM in water with gentle warming

Sicherheit

Toxizität

LD50 oral in mouse: 320mg/kg

Gefahreninformationscode (GHS)

Originator
Vadilex,Carriere,France,1972
Verwenden
vasodilator
Verwenden
Ifenprodil is a NMDA receptor antagonist.
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
Biologische Aktivität
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.