pipamazine

pipamazine Basic information
Product Name:pipamazine
Synonyms:pipamazine;Mornidine;Nausidol;Nometine;RP-9153;SC 9387;1-[3-(2-chlorophenothiazin-10-yl)propyl]isonipecotamide;1-[3-(2-chlorophenothiazin-10-yl)propyl]piperidine-4-carboxamide
CAS:84-04-8
MF:C21H24ClN3OS
MW:401.95
EINECS:201-512-9
Product Categories:
Mol File:84-04-8.mol
pipamazine Structure
pipamazine Chemical Properties
Melting point about 139°
Boiling point 626.6±55.0 °C(Predicted)
density 1.1253 (rough estimate)
refractive index 1.6340 (estimate)
storage temp. Refrigerator
solubility DMSO (Slightly), Methanol (Slightly)
pkapKa 8.60(H2O,t =24±1,I=0.002) (Uncertain)
form Solid
color Off-White to Pale Beige
Safety Information
MSDS Information
pipamazine Usage And Synthesis
OriginatorMornidine ,Searle ,US ,1959
UsesPipamazine is a drug od the phenothiazine class which used to be used as an antiemetic.
DefinitionChEBI: Pipamazine is a member of phenothiazines.
Manufacturing ProcessTo a stirred and refluxing suspension of 4.95 parts of 4piperidinecarboxamide, 1 part of sodium iodide and 8.4 parts of potassium carbonate in 40 parts of butanone there are added in the course of 30 minutes 9.3 parts of 2-chloro-10-(γ-chloropropyl)phenothiazine in 40 parts ofbutanone. Stirring and refluxing are continued for 12 hours after which the mixture is cooled and filtered. The filtrate is concentrated under vacuum to give a residue which is recrystallized from a mixture of 2-propanol and petroleum ether. The 1-[γ-(2'-chloro-10'-phenothiazine)propyl]piperidine-4carboxamide thus obtained melts at approximately 139°C.
This base is dissolved in a small amount of 2-propanol and treated with a 25% solution of hydrogen chloride in 2-propanol. Upon treatment of this solution with anhydrous ether a hydrochloride precipitates as a white solid melting at about 196°C to 197°C with formation of bubbles.
Brand nameNormetine;.
Therapeutic FunctionAntiemetic
World Health Organization (WHO)Pipamazine, which is pharmacologically similar to chlorpromazine, was introduced in 1959 for the treatment of nausea and vomiting. Although it was withdrawn in 1969 by the United States FDA on grounds of lack of proof of efficacy and safety, it remains available in some countries.
pipamazine Preparation Products And Raw materials
Raw materialsHexahydroisonicotinamide
2-Chlorophenothiazine chlorproethazine 1-(3-AMINO-PROPYL)-PIPERIDINE-4-CARBOXYLIC ACID AMIDE 3-(4-METHYL-PIPERIDIN-1-YL)-PROPYLAMINE 3-CHLORODIPHENYLAMINE Chlorpromazine Promazine hydrochloride pipamazine

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