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MedKoo Cat#: 329878 | Name: Pipamperone free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pipamperone is a typical antipsychotic of the butyrophenone family used in the treatment of schizophrenia. Pipamperone acts as an antagonist of the 5-HT2A, 5-HT2B, 5-HT2C D2, D3, D4, α1-adrenergic, and α2-adrenergic receptors. It shows much higher affinity for the 5-HT2A and D4 receptors over the D2 receptor (15-fold in the case of the D4 receptor, and even higher in the case of the 5-HT2A receptor), being regarded as "highly selective" for the former two sites at low doses. Pipamperone has low and likely insignificant affinity for the H1 and mACh receptors, as well as for other serotonin and dopamine receptors.

Chemical Structure

Pipamperone free base
Pipamperone free base
CAS#1893-33-0 (free base)

Theoretical Analysis

MedKoo Cat#: 329878

Name: Pipamperone free base

CAS#: 1893-33-0 (free base)

Chemical Formula: C21H30FN3O2

Exact Mass: 375.2322

Molecular Weight: 375.49

Elemental Analysis: C, 67.17; H, 8.05; F, 5.06; N, 11.19; O, 8.52

Price and Availability

Size Price Availability Quantity
25mg USD 450.00 2 weeks
50mg USD 750.00 2 Weeks
100mg USD 1,250.00 2 weeks
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Related CAS #
1893-33-0 (free base) 2448-68-2 (HCl)
Synonym
Pipamperone, carpiperone; floropipamide; fluoropipamide, floropipamide hydrochloride; R 3345; R-3345; R3345; McN-JR-3345; Brand name: Dipiperon, Dipiperal, Piperonil, Piperonyl, and Propitan.
IUPAC/Chemical Name
1'-(4-(4-fluorophenyl)-4-oxobutyl)-[1,4'-bipiperidine]-4'-carboxamide
InChi Key
AXKPFOAXAHJUAG-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H30FN3O2/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)
SMILES Code
O=C(C1(N2CCCCC2)CCN(CCCC(C3=CC=C(F)C=C3)=O)CC1)N
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Pipamperone was discovered at Janssen Pharmaceutica in 1961, and entered clinical trials in the United States in 1963.
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pipamperone (Floropipamide; McN-JR 3345; R 3345) is a high-affinity antagonist of 5-HT2A receptor (pKi=8.2) and D4 receptor (pKi=8.0) and a low-affinity antagonist of D2 receptor (pKi=6.7).
In vitro activity:
Addition of the dopamine D4 receptor and serotonin 5-HT2A receptor antagonist pipamperone to these cells further increased the expression of the dopamine receptor, reaching 3800 +/- 60 fmol/mg membrane protein. This up-regulation was not restricted to the dopamine D4 receptor but was also found for the serotonin 5-HT2A receptor. This study further provides evidence that the increase in receptor expression is not due to increased mRNA synthesis. As pipamperone could rescue the expression of a folding mutant of the dopamine D4 receptor (M345), this study proposes that pipamperone acts as a pharmacological chaperone for correct receptor folding thereby resulting in an increased dopamine D4 receptor expression. Reference: Life Sci. 2006 Dec 3;80(1):74-81. https://pubmed.ncbi.nlm.nih.gov/16978659/
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
DMSO 100.0 266.32
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 375.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
Van Craenenbroeck K, Gellynck E, Lintermans B, Leysen JE, Van Tol HH, Haegeman G, Vanhoenacker P. Influence of the antipsychotic drug pipamperone on the expression of the dopamine D4 receptor. Life Sci. 2006 Dec 3;80(1):74-81. doi: 10.1016/j.lfs.2006.08.024. Epub 2006 Aug 25. PMID: 16978659.
In vitro protocol:
Van Craenenbroeck K, Gellynck E, Lintermans B, Leysen JE, Van Tol HH, Haegeman G, Vanhoenacker P. Influence of the antipsychotic drug pipamperone on the expression of the dopamine D4 receptor. Life Sci. 2006 Dec 3;80(1):74-81. doi: 10.1016/j.lfs.2006.08.024. Epub 2006 Aug 25. PMID: 16978659.
In vivo protocol:
TBD
1: Giovannoni L, Kullak-Ublick GA, Jetter A. Developing a Model for Quantifying QTc-Prolongation Risk to Enhance Medication Safety Assessment: A Retrospective Analysis. J Pers Med. 2024 Jan 31;14(2):172. doi: 10.3390/jpm14020172. PMID: 38392605; PMCID: PMC10890600. 2: Gangapersad RN, Zhou G, Garcia-Gomez P, Bos J, Hak E, Koch BCP, Schuiling- Veninga CCM, Dierckx B. Comparison of antipsychotic drug use in children and adolescents in the Netherlands before and during the COVID-19 pandemic. Eur Child Adolesc Psychiatry. 2024 Aug;33(8):2695-2703. doi: 10.1007/s00787-023-02340-3. Epub 2024 Jan 6. Erratum in: Eur Child Adolesc Psychiatry. 2024 Apr 20. doi: 10.1007/s00787-024-02434-6. PMID: 38183460; PMCID: PMC11272724. 3: Bohny P, Boettger S, Jenewein J. Dose-dependent QTc interval prolongation under haloperidol and pipamperone in the management of delirium in a naturalistic setting. Front Psychiatry. 2023 Oct 3;14:1257755. doi: 10.3389/fpsyt.2023.1257755. PMID: 37854439; PMCID: PMC10579563. 4: Schulze Westhoff M, Schröder S, Heck J, Pfister T, Jahn K, Krause O, Wedegärtner F, Bleich S, Kahl KG, Krüger THC, Groh A. Determinants of severe QTc prolongation in a real-world gerontopsychiatric setting. Front Psychiatry. 2023 Mar 23;14:1157996. doi: 10.3389/fpsyt.2023.1157996. PMID: 37032947; PMCID: PMC10076587. 5: Guo Y, Li J, Hao F, Yang Y, Yang H, Chang Q, Kong P, Liu W, Jiao X, Teng X. A new perspective on semen quality of aged male: The characteristics of metabolomics and proteomics. Front Endocrinol (Lausanne). 2023 Jan 4;13:1058250. doi: 10.3389/fendo.2022.1058250. PMID: 36686470; PMCID: PMC9848653. 6: Zeiss R, Hafner S, Schönfeldt-Lecuona C, Connemann BJ, Gahr M. Drug- Associated Liver Injury Related to Antipsychotics: Exploratory Analysis of Pharmacovigilance Data. J Clin Psychopharmacol. 2022 Sep-Oct 01;42(5):440-444. doi: 10.1097/JCP.0000000000001576. Epub 2022 Jun 22. PMID: 35730552. 7: Kamp D, Paschali M, Bouanane A, Christl J, Supprian T, Meisenzahl-Lechner E, Kojda G, Lange-Asschenfeldt C. Characteristics of antipsychotic drug-induced hypothermia in psychogeriatric inpatients. Hum Psychopharmacol. 2022 Mar;37(2):e2816. doi: 10.1002/hup.2816. Epub 2021 Sep 17. PMID: 34532905. 8: Beumer S, Hamers P, Oppewal A, Maes-Festen D. Antipsychotics withdrawal in adults with intellectual disability and challenging behaviour: study protocol for a multicentre double-blind placebo-controlled randomised trial. BMC Psychiatry. 2021 Sep 6;21(1):439. doi: 10.1186/s12888-021-03437-2. PMID: 34488701; PMCID: PMC8422779. 9: Obara K, Matsuoka Y, Iwata N, Abe Y, Ikegami Y, Shioda N, Hattori Y, Hamamatsu S, Yoshioka K, Yamaki F, Matsuo K, Yoshio T, Tanaka Y. Inhibitory Effects of Antipsychotics on the Contractile Response to Acetylcholine in Rat Urinary Bladder Smooth Muscles. Biol Pharm Bull. 2021;44(8):1140-1150. doi: 10.1248/bpb.b21-00363. PMID: 34334499. 10: Yang X, Miao Y, Wang J, Mi D. A pan-cancer analysis of the HER family gene and their association with prognosis, tumor microenvironment, and therapeutic targets. Life Sci. 2021 May 15;273:119307. doi: 10.1016/j.lfs.2021.119307. Epub 2021 Mar 8. PMID: 33691171. 11: Hefner G, Hahn M, Hiemke C, Toto S, Wolff J, Roll SC, Klimke A. Pharmacodynamic Drug-Drug interactions of QT-prolonging drugs in hospitalized psychiatric patients. J Neural Transm (Vienna). 2021 Feb;128(2):243-252. doi: 10.1007/s00702-020-02291-y. Epub 2021 Jan 8. PMID: 33417009. 12: van der Esch CCL, Kloosterboer SM, van der Ende J, Reichart CG, Kouijzer MEJ, de Kroon MMJ, van Daalen E, Ester WA, Rieken R, Dieleman GC, Hillegers MHJ, van Gelder T, Koch BCP, Dierckx B. Risk factors and pattern of weight gain in youths using antipsychotic drugs. Eur Child Adolesc Psychiatry. 2021 Aug;30(8):1263-1271. doi: 10.1007/s00787-020-01614-4. Epub 2020 Aug 24. PMID: 32839872; PMCID: PMC8310848. 13: Kloosterboer SM, Egberts KM, de Winter BCM, van Gelder T, Gerlach M, Hillegers MHJ, Dieleman GC, Bahmany S, Reichart CG, van Daalen E, Kouijzer MEJ, Dierckx B, Koch BCP. Pipamperone Population Pharmacokinetics Related to Effectiveness and Side Effects in Children and Adolescents. Clin Pharmacokinet. 2020 Nov;59(11):1393-1405. doi: 10.1007/s40262-020-00894-y. PMID: 32394297; PMCID: PMC7658071. 14: Henning K, Teske J, Klintschar M, Dziadosz M. Postmortem findings of pipamperone after fatal intoxications and its distribution in body fluids and tissues. Drug Test Anal. 2019 Apr;11(4):626-630. doi: 10.1002/dta.2574. Epub 2019 Mar 3. PMID: 30761754. 15: Scholle O, Banaschewski T, Enders D, Garbe E, Riedel O. Use and Characteristics of Antipsychotic/Methylphenidate Combination Therapy in Children and Adolescents with a Diagnosis of Attention-Deficit/Hyperactivity Disorder. J Child Adolesc Psychopharmacol. 2018 Jul/Aug;28(6):415-422. doi: 10.1089/cap.2018.0024. Epub 2018 May 16. PMID: 29768038. 16: van Riet-Nales DA, Nijholt-Faber ED, de Boer A. Druppels: onveilige of onhandige toedieningsvorm? [Oral drops: unsafe or unwieldy method of administration?]. Ned Tijdschr Geneeskd. 2018;162:D2577. Dutch. PMID: 29543146. 17: de Roo JHC, Bosch TM, van Rhijn A, Del Canho R. Overdosering van pipamperon uit een knijpflacon [Overdosing of pipamperone from a squeeze bottle]. Ned Tijdschr Geneeskd. 2018;162:D2160. Dutch. PMID: 29543144. 18: Neumann J, Beck O, Dahmen N, Böttcher M. Potential of Oral Fluid as a Clinical Specimen for Compliance Monitoring of Psychopharmacotherapy. Ther Drug Monit. 2018 Apr;40(2):245-251. doi: 10.1097/FTD.0000000000000493. PMID: 29529010. 19: Kloosterboer SM, de Winter BCM, Bahmany S, Al-Hassany L, Dekker A, Dieleman GC, van Gelder T, Dierckx B, Koch BCP. Dried Blood Spot Analysis for Therapeutic Drug Monitoring of Antipsychotics: Drawbacks of Its Clinical Application. Ther Drug Monit. 2018 Jun;40(3):344-350. doi: 10.1097/FTD.0000000000000502. Erratum in: Ther Drug Monit. 2019 Dec;41(6):772. doi: 10.1097/FTD.0000000000000712. PMID: 29505492. 20: Krämer S, Clark D, Ziegenbein M. Chronischer Verlauf einer Neurolues [Chronic course of neurosyphilis]. Nervenarzt. 2018 May;89(5):586-588. German. doi: 10.1007/s00115-017-0465-1. PMID: 29188351.