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)), 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 inhala ...

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 In biochemistry and pharmacology, a ligand is a substance that forms a complex with a biomolecule to serve a biological purpose. The etymology stems from ''ligare'', which means 'to bind'. In protein-ligand binding, the ligand is usually a mole ...

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, ri ...

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 va ...

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. Dopamine constitutes about 80% o ...

, 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 bet ...

s 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 acid
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(1) gives -(4-methylsulfanylphenyl)sulfanylphenylethanol
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(2). Halogenating with thionyl chloride gives 1-(chloromethyl)-2-(4-methylsulfanylphenyl)sulfanylbenzene
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(3). FGI with cyanide gives 2- -(4-methylsulfanylphenyl)sulfanylphenylcetonitrile
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(4). Alkali hydrolysis of the nitrile to 2- -(4-methylsulfanylphenyl)sulfanylphenylcetic acid
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(5). PPA cyclization to 3-methylsulfanyl-6H-benzo 1]benzothiepin-5-one
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(6). The reduction with sodium borohydride gives 3-methylsulfanyl-5,6-dihydrobenzo 1]benzothiepin-5-ol
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(7). Halogenating with a second round of thionyl chloride gives 5-chloro-3-methylsulfanyl-5,6-dihydrobenzo 1]benzothiepine
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Alkylation with 1-methylpiperazine 09-01-3completed the synthesis of Metitepine (9).

References

External links

* 5-HT1E antagonists 5-HT1F antagonists Alpha-1 blockers Antipsychotics Dibenzothiepines Dopamine antagonists Diphenylethylpiperazines Serotonin receptor antagonists Thioethers {{Nervous-system-drug-stub

Synthesis

See also

References

External links