tipindole

{{Short description|Serotonin antagonist}}

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{{Distinguish|Tepirindole}}

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| CAS_number = 7489-66-9

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| PubChem = 65595

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| ChemSpiderID = 59036

| UNII = US65H9WBNH

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| ChEMBL = 494521

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| synonyms = Tipindol; Typindol; Typindole

| IUPAC_name = 2-(dimethylamino)ethyl 1,3,4,5-tetrahydrothiopyrano[4,3-b]indole-8-carboxylate

| C=16 | H=20 | N=2 | O=2 | S=1

| SMILES = CN(C)CCOC(=O)C1=CC2=C(C=C1)NC3=C2CSCC3

| StdInChI = 1S/C16H20N2O2S/c1-18(2)6-7-20-16(19)11-3-4-14-12(9-11)13-10-21-8-5-15(13)17-14/h3-4,9,17H,5-8,10H2,1-2H3

| StdInChIKey = WNDHLINIYZAWCR-UHFFFAOYSA-N

}}

Tipindole ({{Abbrlink|INN|International Nonproprietary Name}}), also known as typindole, is a drug of the tricyclic family described as a serotonin antagonist and monoamine oxidase inhibitor (MAOI) 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&q=%22typindole%22&pg=RA1-PA287 | access-date=20 October 2024 | page=1-PA287}}{{cite web | title= Tipindole | work = Inxight Drugs | publisher = National Center for Advancing Translational Sciences | url=https://drugs.ncats.io/drug/US65H9WBNH | access-date=20 October 2024}}{{cite journal | vauthors = Ramsay RR, Gravestock MB | title = Monoamine oxidases: to inhibit or not to inhibit | journal = Mini Reviews in Medicinal Chemistry | volume = 3 | issue = 2 | pages = 129–136 | date = March 2003 | pmid = 12570845 | doi = 10.2174/1389557033405287 | quote = A screen using this model identified not only known MAO inhibitors (MAOI) but also similar rigid cyclic compounds such as tipindole, a 5HT receptor agonist, [...] }} The drug was developed by Soviet researchers and was first described by 1962.{{cite journal | vauthors = Aksanova LA, Pidevich IN, Sharkova LM, Kucherova NF | title=Indole derivatives | journal=Pharmaceutical Chemistry Journal | publisher=Springer Science and Business Media LLC | volume=2 | issue=7 | year=1968 | issn=0091-150X | doi=10.1007/bf00759600 | pages=353–359}}