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.
