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| | NAFRONYL Basic information |
| | NAFRONYL Chemical Properties |
| Boiling point | bp0.5 190° | | density | d431 1.0465 | | refractive index | nD29 1.5513 | | storage temp. | Refrigerator | | solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) | | form | Oil | | pka | 9.21±0.25(Predicted) | | color | Colourless to Dark Yellow | | CAS DataBase Reference | 31329-57-4(CAS DataBase Reference) |
| Toxicity | LD50 in mice (mg/kg): 365 orally (Bessin) |
| | NAFRONYL Usage And Synthesis |
| Originator | Dusodril,Roland,W. Germany,1968 | | Uses | Vasodilator. | | Uses | Nafronyl is a selective inhibitor of serotonin receptors. Nafronyl is a vasodilator used in the treatment of intermittent claudication. | | Definition | ChEBI: 2-(1-naphthalenylmethyl)-3-(2-oxolanyl)propanoic acid 2-(diethylamino)ethyl ester is a member of naphthalenes. | | Manufacturing Process | 30 grams (0.106 mol) of β-(1-naphthyl)-β'-tetrahydrofuryl isobutyric acid are
heated under reflux for 8 1/2 hours in 230 cc of isopropanol with 14 grams
(0.103 mol) of β-chloroethyl-N-diethylamine. After evaporation of the
isopropanol in vacuo, the syrupy residue is treated with a solution of K2CO3.
Extraction with ether is carried out after drying over Na2SO4.
Distillation of the extract yields 28.5 grams of a very viscous yellow liquid with
a BP0.95-1.09millibar = 198° to 202°C. The yield is 70.5% (theoretical quantity =
40.5 grams).1.3 grams (0.0103 mol) of dihydrated oxalic acid are dissolved
while being made tepid in 8 cc of acetone. The cooled solution has added
thereto 4 grams (0.0104 mol) of N-diethylaminoethyl-β-(1-naphthyl)-β'-
tetrahydrofuryl isobutyrate, obtained according to the process described above
and dissolved in 10 cc of acetone. The solution is brought to boiling point for
15 minutes. After cooling to ambient temperature, it is placed in a
refrigerator. Crystallization occurs after 2 hours, the crystals which have
formed are separated by centrifuging, and after washing in hexane and drying
in vacuo 3.5 grams of white crystals are obtained. After being recrystallized
three times, in alcohol and then in a mixture of alcohol and ethyl acetate, the
product is analytically pure and has a MP = 110° to 111°C (heating stage). | | Brand name | Praxilene (Lipha, S.A., France). | | Therapeutic Function | Vasodilator | | World Health Organization (WHO) | Naftidrofuryl is a vasoactive spasmolytic used to treat peripheral
vascular disease. It also improves the oxygen utilization in tissues. |
| | NAFRONYL Preparation Products And Raw materials |
| Raw materials | N,N-Dimethylformamide-->Benzyl chloride-->Sodium ethoxide-->alpha-(1-Naphthylmethyl)-2-tetrahydrofuranpropionic acid diethylaminoethyl ester oxalate-->Alkali Metals, plasma standard solution, Specpure, Ba,Be,Ca,Cs,K,Li,Mg,Na,Rb,Sr, 100μg/ml-->Diethylaminoethanol-->Oxalic acid |
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