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P3246

Sigma-Aldrich

Pipamperone dihydrochloride

~99% (HPLC), powder

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Synonym(s):
1′-[4-(4-Fluorophenyl)-4-oxobutyl]-[1,4′-bipiperidine]-4′-carboxamide dihydrochloride, R4050
Empirical Formula (Hill Notation):
C21H30N3O2F · 2HCl
CAS Number:
Molecular Weight:
448.40
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Assay

~99% (HPLC)

Quality Level

form

powder

color

white

solubility

H2O: >2.0 mg/mL

originator

Johnson & Johnson

SMILES string

Cl[H].Cl[H].NC(=O)C1(CCN(CCCC(=O)c2ccc(F)cc2)CC1)N3CCCCC3

InChI

1S/C21H30FN3O2.2ClH/c22-18-8-6-17(7-9-18)19(26)5-4-12-24-15-10-21(11-16-24,20(23)27)25-13-2-1-3-14-25;;/h6-9H,1-5,10-16H2,(H2,23,27);2*1H

InChI key

BMXXSXQVMCXGJM-UHFFFAOYSA-N

Application

Pipamperone dihydrochloride may be used:
  • as an internal standard in liquid chromatography with coulometric detection
  • as an antipsychotic drugs to test its interaction with human ether-a-go-go-related gene (hERG) channel
  • as an internal standard to spike human colostrum samples for reversed phase liquid chromatography- ultraviolet (LC-UV) analysis

Biochem/physiol Actions

Pipamperone, a butyrophenone derivative is a pharmacological chaperone and is a membrane-permeable dopamine receptor D4 (DRD4) antagonist. The affinity of pipamperone is higher for DRD4 and 5-hydroxytryptamine 2A receptor (5-HT2A) in comparison with DRD2. It may be useful therapeutic in treating behavioral disorders and psychomotor agitation symptoms.
D2 dopamine receptor antagonist; 5-HT2 serotonin receptor antagonist; antipsychotic.

Features and Benefits

This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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M Schwaninger et al.
Clinical neuropharmacology, 21(6), 344-346 (1998-12-09)
Hypothermia is a potentially life-threatening emergency. This article examines the case of a 34-year-old, mentally retarded man who experienced three episodes of hypothermia during recurrent exposure to pipamperone. After the pipamperone dose was largely reduced, no further hypothermic episodes occurred.
J E Belgaied et al.
Journal of pharmaceutical and biomedical analysis, 30(4), 1417-1423 (2002-11-01)
The electrochemical reduction of pipamperone has been carried out in aqueous solution in KNO(3) (0.1 mol l(-1)) by differential-pulse polarography (DPP). Pipamperone exhibits a well-defined irreversible reduction peak at -1.3 V/ref. The influence of pH on the reduction of pipamperone
Maria Addolorata Saracino et al.
Talanta, 81(4-5), 1547-1553 (2010-05-06)
A new analytical method, based on the use of liquid chromatography with coulometric detection, has been developed and applied to quantify risperidone and its main active metabolite 9-hydroxyrisperidone in human plasma and saliva. The analytes were separated on a reversed
K Nisijima et al.
Brain research, 890(1), 23-31 (2001-02-13)
The serotonin (5-HT) syndrome is the most serious side effect of antidepressants, and it often necessitates pharmacotherapy. In the present study, the efficacy of several drugs was evaluated in an animal model of the 5-HT syndrome. When 2 mg/kg of
D V Oekelen et al.
European journal of pharmacology, 425(1), 21-32 (2001-10-24)
The 5-HT(2A) and 5-HT(2C) receptors belong to the same subtype of the G-protein coupled receptor family and have several agonist and antagonist ligands in common. To gain more insight into the differences in the regulation of the two receptors, we

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