metitepine

{{Short description|Chemical compound}}

{{Infobox drug

| IUPAC_name = 1-methyl-4-(8-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepin-6-yl)piperazine

| image = Metitepine.svg

| width = 225px

| tradename =

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| routes_of_administration =

| bioavailability =

| protein_bound =

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| CAS_number = 20229-30-5

| CAS_supplemental =
19728-88-2 (maleate)

| ATC_prefix =

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| PubChem = 4106

| IUPHAR_ligand = 89

| ChemSpiderID = 3963

| ChEBI = 64203

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 55D94103HL

| synonyms = Methiothepin; Methiothepine; Ro 8-6837 (maleate); VUFB-6276 (mesylate)

| C=20 | H=24 | N=2 | S=2

| SMILES = CN1CCN(CC1)C2Cc3ccccc3Sc4c2cc(cc4)SC

| StdInChI = 1S/C20H24N2S2/c1-21-9-11-22(12-10-21)18-13-15-5-3-4-6-19(15)24-20-8-7-16(23-2)14-17(18)20/h3-8,14,18H,9-13H2,1-2H3

| StdInChIKey = RLJFTICUTYVZDG-UHFFFAOYSA-N

}}

Metitepine ({{abbrlink|INN|International Nonproprietary Name}}; developmental code names Ro 8-6837 (maleate), VUFB-6276 (mesylate)), also known as methiothepin, is a drug described as a "psychotropic agent" of the tricyclic or tetracyclic group which was never marketed.{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA815|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=815–}}

It acts as a non-selective antagonist of serotonin, dopamine, and adrenergic receptors, including of the serotonin 5-HT₁, 5-HT₂, 5-HT₅, 5-HT₆, and 5-HT₇ receptors.{{cite web | title = PDSP K_i Database | work = Psychoactive Drug Screening Program (PDSP)|author1-link=Bryan Roth | vauthors = Roth BL, Driscol J | publisher = University of North Carolina at Chapel Hill and the United States National Institute of Mental Health | access-date = 14 August 2017 | url = https://pdsp.unc.edu/databases/pdsp.php?knowID=0&kiKey=&receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testLigandDD=&testFreeRadio=testFreeRadio&testLigand=methiothepin&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query}}{{cite web | last=Liu | first=Tiqing | title=BindingDB BDBM78940 METHIOTHEPIN::MLS000859918::Methiothepin mesylate salt::SMR000326779::cid_3039995::mesylic acid;1-methyl-4-[3-(methylthio)-5,6-dihydrobenzo[b][1]benzothiepin-5-yl]piperazine::methanesulfonic acid;1-methyl-4-(3-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazine::methanesulfonic acid;1-methyl-4-[3-(methylthio)-5,6-dihydrobenzo[b][1]benzothiepin-5-yl]piperazine | website=BindingDB | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50122812 | access-date=1 November 2024}}{{cite journal |vauthors=Monachon MA, Burkard WP, Jalfre M, Haefely W | title = Blockade of central 5-hydroxytryptamine receptors by methiothepin | journal = Naunyn-Schmiedeberg's Arch. Pharmacol. | volume = 274 | issue = 2 | pages = 192–7 | year = 1972 | pmid = 4340797 | doi = 10.1007/BF00501854 | s2cid = 19577535 }}{{cite journal |vauthors=Dall'Olio R, Vaccheri A, Montanaro N | title = Reduced head-twitch response to quipazine of rats previously treated with methiothepin: possible involvement of dopaminergic system | journal = Pharmacol. Biochem. Behav. | volume = 23 | issue = 1 | pages = 43–8 | year = 1985 | pmid = 2994121 | doi = 10.1016/0091-3057(85)90128-5 | s2cid = 29894323 }}{{cite journal | vauthors = Chapman ME, Wideman RF | title = Evaluation of the serotonin receptor blockers ketanserin and methiothepin on the pulmonary hypertensive responses of broilers to intravenously infused serotonin | journal = Poult Sci | volume = 85 | issue = 4 | pages = 777–86 | date = April 2006 | pmid = 16615363 | doi = 10.1093/ps/85.4.777 | url = }} The drug has antipsychotic properties.{{cite book| vauthors = Lemke TL, Williams DA |title=Foye's Principles of Medicinal Chemistry |url=https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA388 |date=24 January 2012 |publisher=Lippincott Williams & Wilkins |isbn=978-1-60913-345-0 |pages=388–}}