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
A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...
described as a "
psychotropic agent" of the
tricyclic group which was never marketed.
It acts as a
non-selective
In biochemistry and pharmacology, a ligand is a Chemical substance, substance that forms a Complex (chemistry), complex with a biomolecule to serve a biological purpose. The etymology stems from ''ligare'', which means 'to bind'. In protein-lig ...
antagonist
An antagonist is a character in a story who is presented as the chief foe of the protagonist.
Etymology
The English word antagonist comes from the Greek ἀνταγωνιστής – ''antagonistēs'', "opponent, competitor, villain, enemy, riv ...
of
serotonin
Serotonin () or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter. Its biological function is complex and multifaceted, modulating mood, cognition, reward, learning, memory, and numerous physiological processes such as vomiting and vas ...
,
dopamine
Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic compound, organic chemical of the catecholamine and phenethylamine families. Dopamine const ...
, and
adrenergic receptor
The adrenergic receptors or adrenoceptors are a class of G protein-coupled receptors that are targets of many catecholamines like norepinephrine (noradrenaline) and epinephrine (adrenaline) produced by the body, but also many medications like beta ...
s
and has
antipsychotic
Antipsychotics, also known as neuroleptics, are a class of Psychiatric medication, psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), principally in schizophrenia but ...
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
Clorotepine (; brand names Clotepin, Clopiben), also known as octoclothepin or octoclothepine, is an antipsychotic of the tricyclic group which was derived from perathiepin in 1965 and marketed in the Czech Republic by Spofa in or around 1971 fo ...
*
Perathiepin
Perathiepin is a neuroleptic drug of the tricyclic family which was developed in the 1960s but was never marketed. In animal studies it was found to possess central depressant, antihistamine, antiserotonergic, and analgesic effects.
See also
...
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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