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| | Ifenprodil Basic information |
| Product Name: | Ifenprodil | | Synonyms: | 4-benzyl-alpha-(p-hydroxyphenyl)-beta-methyl-1-piperidineethano;4-benzyl-alpha-(p-hydroxyphenyl)-beta-methyl-1-piperidineethanol;alpha-(4-hydroxyphenyl)-beta-methyl-4-(phenylmethyl)-1-piperidineethano;IFENPRODIL;2-(4-Benzylpiperidino)-1-(4-hydroxyphenyl)-1-propanol tartrate (2:1) salt;1-(4-Hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol;2-(4-Benzylpiperidino)-1-(4-hydroxyphenyl)propan-1-ol;4-Benzyl-α-(p-hydroxyphenyl)-β-methyl-1-piperidineethanol | | CAS: | 23210-56-2 | | MF: | C21H27NO2 | | MW: | 325.45 | | EINECS: | 245-491-4 | | Product Categories: | Glutamate receptor;API | | Mol File: | 23210-56-2.mol |  |
| | 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 |
| Toxicity | LD50 oral in mouse: 320mg/kg |
| | Ifenprodil Usage And Synthesis |
| Originator | Vadilex,Carriere,France,1972 | | Uses | vasodilator | | Uses | 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 | | 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 Preparation Products And Raw materials |
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