Basic information Safety Supplier Related

Difenoxinum

Basic information Safety Supplier Related

Difenoxinum Basic information

Product Name:
Difenoxinum
Synonyms:
  • Difenoxinum
  • 1-(3-Cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylic acid
  • McN-JR-15403-11
  • 1-(3-Cyano-3,3-diphenylpropyl)-4-phenylisonipecotic Acid
  • Difenoxilic Acid
  • Difenoxine
  • Difenoxylic Acid
  • Diphenoxylic Acid
CAS:
28782-42-5
MF:
C28H28N2O2
MW:
424.53
Product Categories:
  • Aromatics
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Metabolites & Impurities
  • Pharmaceuticals
Mol File:
28782-42-5.mol
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Difenoxinum Chemical Properties

Boiling point:
632.7±55.0 °C(Predicted)
Density 
1.175±0.06 g/cm3(Predicted)
solubility 
soluble in DMSO, Methanol
form 
Powder
pka
3.55±0.20(Predicted)
color 
Brown
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Safety Information

HS Code 
2933330000
Toxicity
rat,LD50,oral,149mg/kg (149mg/kg),Drug Development Research. Vol. 1, Pg. 1, 1981.
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Difenoxinum Usage And Synthesis

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.

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