methiothepin on:
[Wikipedia]
[Google]
[Amazon]
Metitepine (; developmental code names Ro 8-6837 (
The reduction of 2-(4-methylsulfanylphenyl)sulfanylbenzoic acid
CID:2733664
(1) gives -(4-methylsulfanylphenyl)sulfanylphenylethanol
CID:12853582
(2). Halogenating with thionyl chloride gives 1-(chloromethyl)-2-(4-methylsulfanylphenyl)sulfanylbenzene
CID:12853583
(3). FGI with cyanide gives 2- -(4-methylsulfanylphenyl)sulfanylphenylcetonitrile
CID:12853584
(4). Alkali hydrolysis of the nitrile to 2- -(4-methylsulfanylphenyl)sulfanylphenylcetic acid
CID:12383832
(5). PPA cyclization to 3-methylsulfanyl-6H-benzo 1]benzothiepin-5-one
CID:827052
(6). The reduction with sodium borohydride gives 3-methylsulfanyl-5,6-dihydrobenzo 1]benzothiepin-5-ol
CID:13597048
(7). Halogenating with a second round of thionyl chloride gives 5-chloro-3-methylsulfanyl-5,6-dihydrobenzo 1]benzothiepine
CID:12404411
Alkylation with 1-methylpiperazine 09-01-3completed the synthesis of Metitepine (9).
maleate
Maleic acid or ''cis''-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO2CCH=CHCO2H. Maleic acid is the ''cis''-isomer of butenedioic acid, whereas fumaric acid ...
), VUFB-6276 (mesylate
In organosulfur chemistry, a mesylate is any salt or ester of methanesulfonic acid (). In salts, the mesylate is present as the anion. When modifying the international nonproprietary name of a pharmaceutical substance containing the group ...
)), also known as methiothepin, is a drug described as a " psychotropic agent" of the tricyclic
Tricyclics are chemical compounds that contain three interconnected rings of atoms.
Many compounds have a tricyclic structure, but in pharmacology, the term has traditionally been reserved to describe heterocyclic drugs. Among these are antid ...
group which was never marketed. It acts as a non-selective antagonist of serotonin, dopamine, and adrenergic receptors and has antipsychotic
Antipsychotics, also known as neuroleptics, are a class of psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), principally in schizophrenia but also in a range of ...
properties.
Synthesis
The reduction of 2-(4-methylsulfanylphenyl)sulfanylbenzoic acidCID:2733664
(1) gives -(4-methylsulfanylphenyl)sulfanylphenylethanol
CID:12853582
(2). Halogenating with thionyl chloride gives 1-(chloromethyl)-2-(4-methylsulfanylphenyl)sulfanylbenzene
CID:12853583
(3). FGI with cyanide gives 2- -(4-methylsulfanylphenyl)sulfanylphenylcetonitrile
CID:12853584
(4). Alkali hydrolysis of the nitrile to 2- -(4-methylsulfanylphenyl)sulfanylphenylcetic acid
CID:12383832
(5). PPA cyclization to 3-methylsulfanyl-6H-benzo 1]benzothiepin-5-one
CID:827052
(6). The reduction with sodium borohydride gives 3-methylsulfanyl-5,6-dihydrobenzo 1]benzothiepin-5-ol
CID:13597048
(7). Halogenating with a second round of thionyl chloride gives 5-chloro-3-methylsulfanyl-5,6-dihydrobenzo 1]benzothiepine
CID:12404411
Alkylation with 1-methylpiperazine 09-01-3completed the synthesis of Metitepine (9).
See also
* Clorotepine * PerathiepinReferences
External links
* 5-HT1E antagonists 5-HT1F antagonists Alpha-1 blockers Antipsychotics Dibenzothiepines Dopamine antagonists Diphenylethylpiperazines Serotonin receptor antagonists Thioethers {{Nervous-system-drug-stub