Metitepine

Metitepine
Clinical data
Other names	Methiothepin; Methiothepine; Ro 8-6837 (maleate); VUFB-6276 (mesylate)
Identifiers
	IUPAC name 1-methyl-4-(8-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepin-6-yl)piperazine;
CAS Number	20229-30-5 ; 19728-88-2 (maleate);
PubChem CID	4106;
IUPHAR/BPS	89;
ChemSpider	3963;
UNII	55D94103HL;
ChEBI	CHEBI:64203;
CompTox Dashboard (EPA)	DTXSID2044000 ;
ECHA InfoCard	100.261.496
Chemical and physical data
Formula	C20H24N2S2
Molar mass	356.55 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCN(CC1)C2Cc3ccccc3Sc4c2cc(cc4)SC;
	InChI InChI=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; Key:RLJFTICUTYVZDG-UHFFFAOYSA-N;

Metitepine (INNTooltip 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.^[1]

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.^[2]^[3]^[4]^[5]^[6] The drug has antipsychotic properties.^[7]

^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 815–. ISBN 978-1-4757-2085-3.
^ Roth BL, Driscol J. "PDSP K_i Database". Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved 14 August 2017.
^ Liu, Tiqing. "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". BindingDB. Retrieved 1 November 2024.
^ Monachon MA, Burkard WP, Jalfre M, Haefely W (1972). "Blockade of central 5-hydroxytryptamine receptors by methiothepin". Naunyn-Schmiedeberg's Arch. Pharmacol. 274 (2): 192–7. doi:10.1007/BF00501854. PMID 4340797. S2CID 19577535.
^ Dall'Olio R, Vaccheri A, Montanaro N (1985). "Reduced head-twitch response to quipazine of rats previously treated with methiothepin: possible involvement of dopaminergic system". Pharmacol. Biochem. Behav. 23 (1): 43–8. doi:10.1016/0091-3057(85)90128-5. PMID 2994121. S2CID 29894323.
^ Chapman ME, Wideman RF (April 2006). "Evaluation of the serotonin receptor blockers ketanserin and methiothepin on the pulmonary hypertensive responses of broilers to intravenously infused serotonin". Poult Sci. 85 (4): 777–86. doi:10.1093/ps/85.4.777. PMID 16615363.
^ Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 388–. ISBN 978-1-60913-345-0.

[Elks2014-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 815–. ISBN 978-1-4757-2085-3.

[PDSPKiDatabase-2] Roth BL, Driscol J. "PDSP K_i Database". Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved 14 August 2017.

[BindingDB-3] Liu, Tiqing. "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". BindingDB. Retrieved 1 November 2024.

[pmid4340797-4] Monachon MA, Burkard WP, Jalfre M, Haefely W (1972). "Blockade of central 5-hydroxytryptamine receptors by methiothepin". Naunyn-Schmiedeberg's Arch. Pharmacol. 274 (2): 192–7. doi:10.1007/BF00501854. PMID 4340797. S2CID 19577535.

[pmid2994121-5] Dall'Olio R, Vaccheri A, Montanaro N (1985). "Reduced head-twitch response to quipazine of rats previously treated with methiothepin: possible involvement of dopaminergic system". Pharmacol. Biochem. Behav. 23 (1): 43–8. doi:10.1016/0091-3057(85)90128-5. PMID 2994121. S2CID 29894323.

[pmid16615363-6] Chapman ME, Wideman RF (April 2006). "Evaluation of the serotonin receptor blockers ketanserin and methiothepin on the pulmonary hypertensive responses of broilers to intravenously infused serotonin". Poult Sci. 85 (4): 777–86. doi:10.1093/ps/85.4.777. PMID 16615363.

[LemkeWilliams2012-7] Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 388–. ISBN 978-1-60913-345-0.

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