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P3246

Sigma-Aldrich

Pipamperone dihydrochloride

~99% (HPLC), powder

Synonym(s):

1′-[4-(4-Fluorophenyl)-4-oxobutyl]-[1,4′-bipiperidine]-4′-carboxamide dihydrochloride, R4050

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About This Item

Empirical Formula (Hill Notation):
C21H30N3O2F · 2HCl
CAS Number:
2448-68-2
Molecular Weight:
448.40
EC Number:
219-507-5
MDL number:
MFCD00242980
UNSPSC Code:
12352200
PubChem Substance ID:
24724576
NACRES:
NA.77

Assay

~99% (HPLC)

Quality Level

100

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
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Eva Saar et al.
Journal of mass spectrometry : JMS, 45(8), 915-925 (2010-07-22)
Over the last decade, the prescription rates of antipsychotic (AP) drugs have increased worldwide. Studies have shown that the risk of sudden cardiac death is threefold higher among patients treated with APs. To investigate the presence of APs in postmortem
A Van Eeckhaut et al.
Journal of clinical pharmacy and therapeutics, 42(3), 306-310 (2017-03-16)
In our university hospital (UZBrussel), one of the options to control post-operative pain after a Caesarean section under general anaesthesia is to administer piritramide by patient-controlled intravenous analgesia (PCIA). As no information is available about the possible transfer of this
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
Kathelijne Peremans et al.
Nuclear medicine communications, 29(8), 724-729 (2008-08-30)
To conduct a cost-efficient pilot study on the effect of low-dose pipamperone on the serotonin-2A receptor binding in a large animal model with conventional single-photon emission tomography modalities. Three healthy drug-naive female Beagle dogs were scanned before and after administration
A G Wade et al.
Psychological medicine, 41(10), 2089-2097 (2011-02-26)
Selective serotonin reuptake inhibitors take several weeks to achieve their full antidepressant effects. Post-synaptic 5-HT2A receptor activation is thought to be involved in this delayed therapeutic effect. Pipamperone acts as a highly selective 5-HT2A/D4 antagonist when administered in low doses.
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