Pipamperone

Overview

Pipamperone (INN, USAN, BAN), sold under the brand name Dipiperon, is a typical antipsychotic of the butyrophenone family used in the treatment of schizophrenia and as a sleep aid for depression. It is or has been marketed under brand names including Dipiperon, Dipiperal, Piperonil, Piperonyl, and Propitan. Pipamperone was discovered at Janssen Pharmaceutica in 1961, and entered clinical trials in the United States in 1963.[1–4] WP

Uses, dosage and effects

Medical uses

Pipamperone was developed for use as an antipsychotic in the treatment of schizophrenia. WP

Pipamperone might be useful as a hallucinogen antidote or "trip killer" in blocking the effects of serotonergic psychedelics like psilocybin.[5] WP

Pharmacology

Pharmacology

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.[6–12] WP

Pipamperone is considered to have been a forerunner to the atypical antipsychotics, if not an atypical antipsychotic itself, due to its prominent serotonin antagonism. It is also used to normalise mood and sleep patterns and has antianxiety effects in neurotic patients.[13–16] WP⚠ A table follows this text in the source and is not copied here. Open the source to see it.

Chemistry

Formula

C21H30FN3O2 PC

CAS number

1893-33-0 PC

Molar mass (g/mol)

375.5 PC

IUPAC name (computed by PubChem)

1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidin-1-ylpiperidine-4-carboxamide PC

SMILES

C1CCN(CC1)C2(CCN(CC2)CCCC(=O)C3=CC=C(C=C3)F)C(=O)N PC

InChIKey

AXKPFOAXAHJUAG-UHFFFAOYSA-N PC

PubChem CID

4830

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Morton IK, Hall JM. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 31 October 1999
2. Other Elks J. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014
3. Journal / agency Ansoms C, Backer-Dierick GD, Vereecken JL. Sleep disorders in patients with severe mental depression: double-blind placebo-controlled evaluation of the value of pipamperone (Dipiperon). Acta Psychiatrica Scandinavica. February 1977. doi:10.1111/j.1600-0447.1977.tb00147.x · PMID 320830
4. Other Healy D. The Creation of Psychopharmacology. 1 July 2009
5. Journal / agency Halman A, Kong G, Sarris J, Perkins D. Drug-drug interactions involving classic psychedelics: A systematic review. J Psychopharmacol. January 2024. doi:10.1177/02698811231211219 · PMID 37982394 · PMC10851641
6. Journal / agency Schotte A, Janssen PF, Gommeren W, Luyten WH, Van Gompel P, Lesage AS, De Loore K, Leysen JE. Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding. Psychopharmacology. March 1996. doi:10.1007/bf02245606 · PMID 8935801
7. Journal / agency Wainscott DB, Lucaites VL, Kursar JD, Baez M, Nelson DL. Pharmacologic characterization of the human 5-hydroxytryptamine2B receptor: evidence for species differences. The Journal of Pharmacology and Experimental Therapeutics. February 1996. doi:10.1016/S0022-3565(25)12346-X · PMID 8632342
8. Journal / agency Prinssen EP, Koek W, Kleven MS. 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. January 2000. doi:10.1016/s0014-2999(99)00859-6 · PMID 10657547
9. Other Leyson JE. Atypical Antipsychotics. 6 December 2012
10. Journal / agency 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 Sciences. December 2006. doi:10.1016/j.lfs.2006.08.024 · PMID 16978659
11. Journal / agency Wade AG, Crawford GM, Nemeroff CB, Schatzberg AF, Schlaepfer T, McConnachie A, Haazen L, Buntinx E. 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. Psychological Medicine. October 2011. doi:10.1017/S0033291711000158 · PMID 21349239
12. Other Abi-Dargham A, Krystal J. Neurotransmitter Receptors in Actions of Antipsychotic Medications. 22 June 2000
13. Journal / agency Awouters FH, Lewi PJ. Forty years of antipsychotic Drug research--from haloperidol to paliperidone--with Dr. Paul Janssen. Arzneimittel-Forschung. 2007. doi:10.1055/s-0031-1296660 · PMID 18074755
14. Journal / agency Vanden Bussche G, Gelders YG, Heylen SL. Development of new antipsychotic drugs. Acta Psiquiatrica y Psicologica de America Latina. 1990. PMID 2127339
15. Journal / agency Niemegeers CJ, Awouters F, Janssen PA. Serotonin antagonism involved in the antipsychotic effect. Confirmation with ritanserine and risperidone. L'Encéphale. 1990. PMID 1693560
16. Other Psychotropic Agents: Part I: Antipsychotics and Antidepressants. 2012-12-06

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.