Metitepine (; developmental code names Ro 8-6837 (
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
![Metitepine synthesis](https://upload.wikimedia.org/wikipedia/commons/b/bc/Metitepine_synthesis.svg)
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).
See also
*
Clorotepine
*
Perathiepin
References
External links
*
5-HT1E antagonists
5-HT1F antagonists
Alpha-1 blockers
Antipsychotics
Dibenzothiepines
Dopamine antagonists
Diphenylethylpiperazines
Serotonin receptor antagonists
Thioethers
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