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Difenoxinum

Difenoxinum
Difenoxinum structure
CAS No.
28782-42-5
Chemical Name:
Difenoxinum
Synonyms
Difenoxine;Difenoxinum;McN-JR-15403-11;Difenoxilic Acid;Difenoxylic Acid;Diphenoxylic Acid;Diphenoxylate Impurity A;UFIVBRCCIRTJTN-UHFFFAOYSA-N;Diphenoxylate EP impurity A;1-(3-Cyano-3,3-diphenylpropyl)-4-phenylisonipecotic Acid
CBNumber:
CB01178506
Molecular Formula:
C28H28N2O2
Formula Weight:
0
MOL File:
28782-42-5.mol

Difenoxinum Properties

Boiling point:
632.7±55.0 °C(Predicted)
Density 
1.175±0.06 g/cm3(Predicted)
pka
3.55±0.20(Predicted)
SAFETY
  • Risk and Safety Statements
HS Code  2933330000

Difenoxinum Chemical Properties,Uses,Production

Originator

Lyspafena,Cilag Chemie,W. Germany,1980

Uses

The active metabolite of Diphenoxylate. Antiperistaltic; antidiarrheal. This is a controlled substance (opiate).

Definition

ChEBI: A piperidinemonocarboxylic acid that is 4-phenylpiperidine-4-carboxylic acid in which the hydrogen attached to the nitrogen atom is substituted by a 3-cyano-3,3-diphenylpropyl group.

Manufacturing Process

To a stirred solution of 5.52 parts of t-potassiurn butanolate in 60 parts of dimethylsulfoxide are added 1.7 parts of ethyl-1-(3-cyano-3,3- diphenylpropyl)-4-phenylisonipecotate hydrochloride and the whole is stirred on an oil bath (90°C) for 4 hours. The reaction mixture is cooled (30°C) and poured onto 180 parts of water with stirring. After two extractions with benzene, the aqueous phase is acidified with glacial acetic acid to pH 6.5 with stirring. The precipitated product is filtered off, washed with water, dried, dissolved in 50 parts of 0.4 N potassium hydroxide and precipitated again with glacial acetic acid. The crude free base is filtered off and dissolved in a mixture of 2-propanol and chloroform and gaseous hydrogen chloride is introduced into the solution. The whole is filtered and the filtrate is evaporated. The residue is mixed with benzene and the latter is evaporated again. The residue is recrystallized from 2-propanol, yielding 1-(3-cyano-3,3- diphenylpropyl)-4-phenylisonipecotic acid hydrochloride.

brand name

Dioctin;Lyspafen;Lyspofenac;Motofen.

Therapeutic Function

Antiperistaltic

World Health Organization (WHO)

Difenoxin is the principal metabolite of diphenoxylate. See WHO comment for diphenoxylate.

Difenoxinum Preparation Products And Raw materials

Raw materials

Preparation Products

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