| Iupac Name: | 1-methyl-4-(8-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepin-6-yl)piperazine |
| Width: | 225px |
| Cas Number: | 20229-30-5 |
| Cas Supplemental: | 19728-88-2 (maleate) |
| Pubchem: | 4106 |
| Iuphar Ligand: | 89 |
| Chemspiderid: | 3963 |
| Chebi: | 64203 |
| 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 (; 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.[1] It acts as a non-selective antagonist of serotonin, dopamine, and adrenergic receptors[2] [3] [4] and has antipsychotic properties.[5]
The reduction of 2-(4-methylsulfanylphenyl)sulfanylbenzoic acid, CID:2733664 (1) gives [2-(4-methylsulfanylphenyl)sulfanylphenyl]methanol, CID:12853582 (2). Halogenating with thionyl chloride gives 1-(chloromethyl)-2-(4-methylsulfanylphenyl)sulfanylbenzene, CID:12853583 (3). FGI with cyanide gives 2-[2-(4-methylsulfanylphenyl)sulfanylphenyl]acetonitrile, CID:12853584 (4). Alkali hydrolysis of the nitrile to 2-[2-(4-methylsulfanylphenyl)sulfanylphenyl]acetic acid, CID:12383832 (5). PPA cyclization to 3-methylsulfanyl-6H-benzo[b][1]benzothiepin-5-one, CID:827052 (6). The reduction with sodium borohydride gives 3-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepin-5-ol, CID:13597048 (7). Halogenating with a second round of thionyl chloride gives 5-chloro-3-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepine, CID:12404411. Alkylation with 1-methylpiperazine [109-01-3] completed the synthesis of Metitepine (9).