Tepirindole

{{Short description|Abandoned antipsychotic drug}}

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{{Distinguish|Tipindole}}

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| class = Atypical antipsychotic; Major tranquilizer

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| CAS_number = 72808-81-2

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| PubChem = 68915

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| ChemSpiderID = 62142

| UNII = X235XX30GK

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| ChEMBL = 2105413

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| synonyms = RU-27592; HR-592

| IUPAC_name = 5-chloro-3-(1-propyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indole

| C=16 | H=19 | Cl=1 | N=2

| SMILES = CCCN1CCC(=CC1)C2=CNC3=C2C=C(C=C3)Cl

| StdInChI = 1S/C16H19ClN2/c1-2-7-19-8-5-12(6-9-19)15-11-18-16-4-3-13(17)10-14(15)16/h3-5,10-11,18H,2,6-9H2,1H3

| StdInChIKey = ZRCUMOBNOPSLKM-UHFFFAOYSA-N

}}

Tepirindole ({{Abbrlink|INN|International Nonproprietary Name}}; developmental code names RU-27592, HR-592) is a tryptamine-related atypical antipsychotic and major tranquilizer which was never marketed.{{cite book | vauthors = Elks J | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA1159 | access-date=8 October 2024 | page=1159}}{{cite book | vauthors = Milne GW | title=Drugs: Synonyms and Properties | publisher=Wiley | year=2002 | isbn=978-0-566-08491-1 | url=https://books.google.com/books?id=QxcoEAAAQBAJ&pg=PA676 | access-date=8 October 2024 | page=676}}{{cite journal | vauthors = Seeman P | title = Atypical neuroleptics: role of multiple receptors, endogenous dopamine, and receptor linkage | journal = Acta Psychiatrica Scandinavica. Supplementum | volume = 358 | issue = | pages = 14–20 | date = 1990 | pmid = 1978482 | doi = 10.1111/j.1600-0447.1990.tb05280.x }}{{cite book | vauthors = Vinick F, Heym JH | title=Annual Reports in Medicinal Chemistry | chapter=Chapter 1 Antipsychotic Agents | publisher=Elsevier | year=1987 | volume=22 | issn=0065-7743 | doi=10.1016/s0065-7743(08)61149-5 | page=1–10 | isbn=978-0-12-040522-0 | quote=Several potent blockers of DA receptors are also putative atypical antipsychotics. Tepirindole (HR-592, 25) has a high affinity for DA, 5-HT and NE receptors but has little propensity to cause catalepsy (78).}}{{cite journal | vauthors = Gomita Y, Ichimaru Y, Moriyama M, Furuno K, Suemaru K, Osman FE, Araki Y | title = Behavioral effects of HR-592, a new derivative of indole | journal = Japanese Journal of Pharmacology | volume = 52 | issue = 4 | pages = 609–619 | date = April 1990 | pmid = 2342229 | doi = 10.1254/jjp.52.609 | doi-access = free }} It is similar in structure to tryptamines but is not technically a tryptamine itself and is instead a piperidinyl indole. The drug is said to act on dopamine D₂, serotonin 5-HT₂, and α₁-adrenergic receptors. It is a potent dopamine receptor antagonist but reportedly has little propensity to cause catalepsy and has been said to potentially be useful in treating the negative symptoms of schizophrenia. The drug may also act as a potent serotonin receptor agonist.{{cite journal | vauthors = Euvrard C, Boissier JR | title = Biochemical assessment of the central 5-HT agonist activity of RU 24969 (a piperidinyl indole) | journal = European Journal of Pharmacology | volume = 63 | issue = 1 | pages = 65–72 | date = April 1980 | pmid = 6155275 | doi = 10.1016/0014-2999(80)90117-x }} Tepirindole was first described in the literature by 1979.