84-04-8

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 NO: 84-04-8
• Molecular Formula: C₂₁H₂₄ClN₃OS
• Molecular Weight: 401.96
• EINECS: 201-512-9
• Mol File: 84-04-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: about 139°
• Boiling Point: 626.6°C at 760 mmHg
• Flash Point: 332.8°C
• Appearance: /
• Density: 1.1253 (rough estimate)
• Vapor Pressure: 1.29E-15mmHg at 25°C
• Refractive Index: 1.6340 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: pKa 8.60(H2O,t =24±1,I=0.002) (Uncertain)
• CAS DataBase Reference: pipamazine(CAS DataBase Reference)
• NIST Chemistry Reference: pipamazine(84-04-8)
• EPA Substance Registry System: pipamazine(84-04-8)

Safety Data

• Hazardous Substances Data: 84-04-8(Hazardous Substances Data)

Usage

Description

Pipamazine, a member of the phenothiazine class of drugs, is a pharmaceutical compound that was historically utilized for its antiemetic properties. It is known by the brand name Normetine.

Uses

Used in Pharmaceutical Industry:
Pipamazine is used as an antiemetic agent for the treatment of nausea and vomiting. It functions by blocking the action of certain neurotransmitters in the brain, thereby alleviating the symptoms associated with these conditions.

Originator

Mornidine ,Searle ,US ,1959

Manufacturing Process

To 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.

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.

InChI:InChI=1/C21H24ClN3OS/c22-16-6-7-20-18(14-16)25(17-4-1-2-5-19(17)27-20)11-3-10-24-12-8-15(9-13-24)21(23)26/h1-2,4-7,14-15H,3,8-13H2,(H2,23,26)

Downstream Products

• 2765-59-5 2-chloro-10-(3-chloropropyl)-10H-phenothiazine 

Relevant articles and documents

Stability of some phenothiazine free radicals.

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