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)

Safety Information

Toxicity

LD50 in mice (mg/kg): 365 orally (Bessin)

NAFRONYL Usage And Synthesis

Originator

Dusodril,Roland,W. Germany,1968

Uses

Nafronyl is a selective inhibitor of serotonin receptors. Nafronyl is a vasodilator used in the treatment of intermittent claudication.

Uses

Vasodilator.

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(31329-57-4)Related Product Information

• NAFRONYL OXALATE SALT,NAFRONYL OXALATE,Nafronyl acid oxalate,Nafronyl oxalate salt ,98%,Nafronyl oxalate salt ,99%
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• NAFTIDROFURYL IMPURITY C3-[(NAPHTALEN-1-YL)-2-[(NAPHTALEN-1-YL)METHYL]PROPANOATE EPY(CRM STANDARD)
• NAFTIDROFURYL OXALATE ASSAY STANDARD BP(CRM STANDARD)
• NAFTIDROFURYL IMPURITY A2-[(NAPHTALEN-1-YL)METHYL]-3-(TETRAHYDROFURAN-2-YL)PROPANOIC ACID EPY(CRM STANDARD)
• NAFTIDROFURYL IMPURITY F2-[(DIETHYLAMINO)ETHYL 2-[(NAPHTHALEN-2-YL)METHYL]-3-(TETRAHYDROFURAN-2-YL)PROPANOATE EPY(CRM STANDARD)
• NAFTIDROFURYL OXALATE BP STANDARD(CRM STANDARD)
• NAFTIDROFURYL IMPURITY B2-[(NAPHTALEN-1-YL)METHYL]-3-(TETRAHYDROFURAN-2-YL)PROPANOATE EPY(CRM STANDARD)
• NAFTIDROFURYL HYDROGEN OXALATE MM(CRM STANDARD)
• NAFTIDROFURYL HYDROGEN OXALATE REFERENCE SPECTRUM EPY(CRM STANDARD)