metitepine metitepine metitepine (inn; 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 group which was never marketed. it acts as a non-selective antagonist of serotonin, dopamine, and adrenergic receptors and has antipsychotic properties. metitepineclinical dataother namesmethiothepin; methiothepine; ro 8-6837 (maleate); vufb-6276 (mesylate)identifiers iupac name 1-methyl-4-(8-methylsulfanyl-5,6-dihydrobenzobenzothiepin-6-yl)piperazine cas number20229-30-5 19728-88-2 (maleate)pubchem cid4106iuphar/bps89chemspider3963unii55d94103hlchebichebi:64203comptox dashboard (epa)dtxsid2044000 echa infocard100.261.496 chemical and physical dataformulac20h24n2s2molar mass356.55 g·mol−13d 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,9-13h2,1-2h3key:rljfticutyvzdg-uhfffaoysa-n synthesis synthesis: the reduction of 2-(4-methylsulfanylphenyl)sulfanylbenzoic acid, cid:2733664 (1) gives methanol, cid:12853582 (2). halogenating with thionyl chloride gives 1-(chloromethyl)-2-(4-methylsulfanylphenyl)sulfanylbenzene, cid:12853583 (3). fgi with cyanide gives 2-acetonitrile, cid:12853584 (4). alkali hydrolysis of the nitrile to 2-acetic acid, cid:12383832 (5). ppa cyclization to 3-methylsulfanyl-6h-benzobenzothiepin-5-one, cid:827052 (6). the reduction with sodium borohydride gives 3-methylsulfanyl-5,6-dihydrobenzobenzothiepin-5-ol, cid:13597048 (7). halogenating with a second round of thionyl chloride gives 5-chloro-3-methylsulfanyl-5,6-dihydrobenzobenzothiepine, cid:12404411. alkylation with 1-methylpiperazine completed the synthesis of metitepine (9).