Fomocaine
Fomocaine Basic information
- Product Name:
- Fomocaine
- Synonyms:
-
- Fomocaine
- fomocain
- 4-(3-(4-(PHENOXYMETHYL)PHENYL)PROPYL)MORPHOLINE
- P-652
- Panacain
- p-Fomocaine
- Morpholine, 4-[3-[4-(phenoxymethyl)phenyl]propyl]-
- CAS:
- 17692-39-6
- MF:
- C20H25NO2
- MW:
- 311.42
- Mol File:
- 17692-39-6.mol
Fomocaine Chemical Properties
- Melting point:
- 52-53°
- Boiling point:
- bp1.1 238-240°
- Density
- 1.0899 (rough estimate)
- refractive index
- 1.5614 (estimate)
- pka
- 7.44±0.10(Predicted)
- color
- Crystals from pet ether
Fomocaine Usage And Synthesis
Originator
Erbocain,Heilit,W. Germany,1967
Definition
ChEBI: Fomocaine is an amine.
Manufacturing Process
64 parts of dry sodium phenolate are dissolved in 300 parts of methylisobutyl
ketone by heating at 110°C. 103 parts of γ-(4-chloromethylphenyl)propyl
chloride are added dropwise with agitation, and the mixture is maintained at
110°C for a period of 4 hours with constant agitation. After cooling, the
reaction mixture is washed 2 or 3 times with 100 parts of water and the
methylisobutyl ketone is distilled off under reduced pressure. The residue is
taken up in 200 parts of petroleum ether and γ-(4-phenoxymethylphenyl)
propyl chloride is crystallized by addition of ice water. The crystals are filtered
off employing a suction pump and dried at 100°C in vacuo (10 mm Hg) for 1
to 2 hours. The γ-(4-phenoxymethylphenyl)propyl chloride melts at 55°C to
56°C after recrystallization from petroleum ether.
130 parts of γ-(4-phenoxymethylphenyl)propyl chloride are heated under
reflux at 140°C for 24 hours with 130 parts of morpholine. The reaction
mixture is treated to give N-[(γ-phenoxymethylphenyl)propyl]-morpholine,
which forms colorless crystals melting at 52°C to 53°C when crystallized from
n-heptane.
Therapeutic Function
Local anesthetic
Safety Profile
Poison by intravenous and intraperitoneal routes. Moderately toxic by subcutaneous route. When heated to decomposition it emits toxic fumes of NOx.