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Clinical data
Trade namesDipiperon
Other namesMcN-JR 3345; R-3345
AHFS/Drugs.comInternational Drug Names
Routes of
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life17-22 hours
Duration of action0.5-1 hour
  • 1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidin-1-ylpiperidine-4-carboxamide
CAS Number
PubChem CID
CompTox Dashboard (EPA)
ECHA InfoCard100.119.828 Edit this at Wikidata
Chemical and physical data
Molar mass375.488 g·mol−1
3D model (JSmol)
  • Fc1ccc(cc1)C(=O)CCCN3CCC(C(=O)N)(N2CCCCC2)CC3
  • 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) checkY
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Pipamperone (INN, USAN, BAN), also known as carpiperone and floropipamide or fluoropipamide, and as floropipamide hydrochloride (JAN), is a typical antipsychotic of the butyrophenone family used in the treatment of schizophrenia[2][3] and as a sleep aid for depression.[4] It is or has been marketed under brand names including Dipiperon, Dipiperal, Piperonil, Piperonyl, and Propitan.[3] Pipamperone was discovered at Janssen Pharmaceutica in 1961, and entered clinical trials in the United States in 1963.[5]


Pipamperon Neuraxpharm, 40mg

Pipamperone acts as an antagonist of the 5-HT2A,[6] 5-HT2B,[7] 5-HT2C[8] D2,[6] D3,[9] D4,[6][10] α1-adrenergic,[9] and α2-adrenergic receptors.[9] 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),[6][9][11] being regarded as "highly selective" for the former two sites at low doses.[11][12] Pipamperone has low and likely insignificant affinity for the H1 and mACh receptors, as well as for other serotonin and dopamine receptors.[9]

Pipamperone is considered to have been a forerunner to the atypical antipsychotics, if not an atypical antipsychotic itself, due to its prominent serotonin antagonism.[13][14][15] It is also used to normalise mood and sleep patterns and has antianxiety effects in neurotic patients.[16]

Site pKi
D1 5.61
D2 6.71
D3 6.58
D4 7.95
5 HT1A 5.46
5 HT1B 5.54
5 HT1D 6.14
5 HT1E 5.44
5 HT1F <5
5-HT2A 8.19
5 HT5 5.35
5 HT7 6.26
α1 7.23
α2A 6.15
α2B 7.08
α2C 6.25

Antidepressant effects[edit]

Low-dose pipamperone (5 mg twice daily) has been found to accelerate and enhance the antidepressant effect of citalopram (40 mg once daily), in a combination (citalopram/pipamperone) referred to as PipCit (code name PNB-01).[11][18]

See also[edit]


  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 222–. ISBN 978-0-7514-0499-9.
  3. ^ a b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 985–. ISBN 978-1-4757-2085-3.
  4. ^ Ansoms C, Backer-Dierick GD, Vereecken JL (February 1977). "Sleep disorders in patients with severe mental depression: double-blind placebo-controlled evaluation of the value of pipamperone (Dipiperon)". Acta Psychiatrica Scandinavica. 55 (2): 116–122. doi:10.1111/j.1600-0447.1977.tb00147.x. PMID 320830. S2CID 40758854.
  5. ^ Healy D (1 July 2009). The Creation of Psychopharmacology. Harvard University Press. pp. 251–. ISBN 978-0-674-03845-5.
  6. ^ a b c d Schotte A, Janssen PF, Gommeren W, Luyten WH, Van Gompel P, Lesage AS, et al. (March 1996). "Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding". Psychopharmacology. 124 (1–2): 57–73. doi:10.1007/bf02245606. PMID 8935801. S2CID 12028979.
  7. ^ Wainscott DB, Lucaites VL, Kursar JD, Baez M, Nelson DL (February 1996). "Pharmacologic characterization of the human 5-hydroxytryptamine2B receptor: evidence for species differences". The Journal of Pharmacology and Experimental Therapeutics. 276 (2): 720–727. PMID 8632342.
  8. ^ Prinssen EP, Koek W, Kleven MS (January 2000). "The effects of antipsychotics with 5-HT(2C) receptor affinity in behavioral assays selective for 5-HT(2C) receptor antagonist properties of compounds". European Journal of Pharmacology. 388 (1): 57–67. doi:10.1016/s0014-2999(99)00859-6. PMID 10657547.
  9. ^ a b c d e Leyson JE (6 December 2012). "Receptor profile of antipsychotics". In Ellenbroek BA, Cools AR (eds.). Atypical Antipsychotics. Birkhäuser. pp. 62–. ISBN 978-3-0348-8448-8.
  10. ^ Van Craenenbroeck K, Gellynck E, Lintermans B, Leysen JE, Van Tol HH, Haegeman G, Vanhoenacker P (December 2006). "Influence of the antipsychotic drug pipamperone on the expression of the dopamine D4 receptor". Life Sciences. 80 (1): 74–81. doi:10.1016/j.lfs.2006.08.024. PMID 16978659.
  11. ^ a b c Wade AG, Crawford GM, Nemeroff CB, Schatzberg AF, Schlaepfer T, McConnachie A, et al. (October 2011). "Citalopram plus low-dose pipamperone versus citalopram plus placebo in patients with major depressive disorder: an 8-week, double-blind, randomized study on magnitude and timing of clinical response" (PDF). Psychological Medicine. 41 (10): 2089–2097. doi:10.1017/S0033291711000158. PMID 21349239. S2CID 19189492.
  12. ^ Abi-Dargham A, Krystal J (22 June 2000). "Serotonin Receptors as Targets of Antipsychotic Medications". In Lidow MS (ed.). Neurotransmitter Receptors in Actions of Antipsychotic Medications. CRC Press. pp. 88–. ISBN 978-1-4200-4177-4.
  13. ^ Awouters FH, Lewi PJ (2007). "Forty years of antipsychotic Drug research--from haloperidol to paliperidone--with Dr. Paul Janssen". Arzneimittel-Forschung. 57 (10): 625–632. doi:10.1055/s-0031-1296660. PMID 18074755. S2CID 5713281.
  14. ^ Vanden Bussche G, Gelders YG, Heylen SL (1990). "[Development of new antipsychotic drugs]". Acta Psiquiatrica y Psicologica de America Latina (in Spanish). 36 (1–2): 13–25. PMID 2127339.
  15. ^ Niemegeers CJ, Awouters F, Janssen PA (1990). "[Serotonin antagonism involved in the antipsychotic effect. Confirmation with ritanserine and risperidone]". L'Encéphale (in French). 16 (2): 147–151. PMID 1693560.
  16. ^ Psychotropic Agents: Part I: Antipsychotics and Antidepressants. Springer Science & Business Media. 2012-12-06. ISBN 9783642675386.
  17. ^ Bart A. Ellenbroek, Alexander R. Cools (eds.) (6 December 2012). Atypical Antipsychotics. Basel: Birkhäuser, pp. 62 f. ISBN 978-3-0348-8448-8.
  18. ^ Kirk R (February 2010). "Clinical trials in CNS--SMi's eighth annual conference". IDrugs. 13 (2): 66–69. PMID 20127552.