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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

D2 dopamine receptor antagonist; 5-HT2 serotonin receptor antagonist; antipsychotic.
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.

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000306382
0000306382
0000275719
123K4708

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P A Janssen et al.
Arzneimittel-Forschung, 44(3), 269-277 (1994-03-01)
In 1965 the first study of this series reported different effects of neuroleptics in rats, supporting clinical differences. At the one end, haloperidol presented as a potent and specific antagonist of the psychostimulants amphetamine and apomorphine. Haloperidol-like neuroleptics have marked
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
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
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
The treatment of autism with pipamperone: A case report
Petrosino B, et al.
European Psychiatry : The Journal of the Association of European Psychiatrists, 33, S682-S682 (2016)
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