84-02-6

Basic information

• Product Name: PROCHLORPERAZINE MALEATE
• Synonyms: 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-phenothiazinmaleate(1:2);buccastem;emetiral;enedioate(1:2);meterazinmaleate;nibromina;pasotomin;prochloroproazinehydrogenmaleate
• CAS NO: 84-02-6
• Molecular Formula: 2C₄H₄O₄*C₂₀H₂₄ClN₃S
• Molecular Weight: 606.09
• EINECS: 201-511-3
• Product Categories: Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Antagonists;Dopaminergics;Neurotransmitters
• Mol File: 84-02-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 1750C
• Boiling Point: 524.8 °C at 760 mmHg
• Flash Point: 271.2 °C
• Appearance: Off-White Powder
• Vapor Pressure: 6.76E-32mmHg at 25°C
• Storage Temp.: Store at RT
• Solubility: Very slightly soluble in water and in ethanol (96 per cent).
• PKA: pKa 8.1(H2O,t =24±1) (Uncertain)
• Stability: Stable for 2 years as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• Merck: 14,7761
• CAS DataBase Reference: PROCHLORPERAZINE MALEATE(CAS DataBase Reference)
• NIST Chemistry Reference: PROCHLORPERAZINE MALEATE(84-02-6)
• EPA Substance Registry System: PROCHLORPERAZINE MALEATE(84-02-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: SO3150000
• Hazardous Substances Data: 84-02-6(Hazardous Substances Data)

Usage

Description

Prochlorperazine maleate (84-02-6) inhibits dynamin and clathrin-mediated endocytosis (CME) with an IC50=5.8 μM for CME.1?Increases tumor cell antigen presentation enhancing the efficacy of anti-tumor mAbs.2?A clinically useful antipsychotic agent3?with antimigraine4?and antiemetic activity5.

Chemical Properties

Off-White Powder

General Description

Prochlorperazinemaleate, 2-chloro-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazinemaleate (Compazine), is in the piperazine subgroupof the phenothiazines, characterized by high-milligramantipsychotic potency, a high prevalence of EPS, and lowsedative and autonomic effects. Prochlorperazine is more potenton a milligram basis than its alkylamino counterpart,chlorpromazine. Because of the high prevalence of EPS, however,it is used mainly for its antiemetic effect, not for its antipsychoticeffect.

Biological Activity

D 2 receptor antagonist. Also interacts with 5-HT 3 and nAChR. Displays antipsychotic, antispasmodic, antiemetic and antinociceptive activity in vivo .

Biochem/physiol Actions

Phenothiazine antipsychotic; D2 dopamine receptor antagonist; antispasmodic

References

References/Citations 1) Daniel?et al.?(2015),?Phenothiazine-derived antipsychotic drugs inhibit dynamin and clathrin-mediated endocytosis; Traffic,?16?635 2) Chew?et al.?(2020),?Endocytosis Inhibition in Humans to Improve Responses to ADCC-Mediating Antibodies; Cell,?180?895 3) Hollister?et al.?(1969),?Clinical use of psychotherapeutic drugs: current status;?Clin. Pharmacol. Ther.,?10?170 4) Cook and Newberry (2018),?Emergency Department Use of Intravenous Prochlorperazine for Acute Migraine; Adv. Emerg. Nurs. J.,?40?148 5) Van den Berg?et al.?(1996),?The prophylactic antiemetic efficacy of prochlorperazine and ondansetron in nasal septal surgery: a randomized double-blind comparison; Anaesth. Intensive Care,?24?538

InChI:InChI=1/C20H24ClN3S.2C4H4O4/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24;2*5-3(6)1-2-4(7)8/h2-3,5-8,15H,4,9-14H2,1H3;2*1-2H,(H,5,6)(H,7,8)