Metitepine (; developmental code names Ro 8-6837 ( maleate), 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 inhal ...

described as a "

psychotropic agent A psychoactive drug, psychopharmaceutical, psychoactive agent or psychotropic drug is a chemical substance, that changes functions of the nervous system, and results in alterations in perception, mood, consciousness, cognition or behavior. ...

" 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 anti ...

group which was never marketed. It acts as a non-selective antagonist of serotonin,

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 8 ...

, 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 psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), principally in schizophrenia but also in a range o ...

properties.

Synthesis

The reduction of 2-(4-methylsulfanylphenyl)sulfanylbenzoic acid
CID:2733664
(1) gives

-(4-methylsulfanylphenyl)sulfanylphenyl The hyphen-minus is the most commonly used type of hyphen, widely used in digital documents. It is the only character that looks like a minus sign or a dash in many character sets such as ASCII or on most keyboards, so it is also used as such. ...

ethanol
CID:12853582
(2). Halogenating with thionyl chloride gives 1-(chloromethyl)-2-(4-methylsulfanylphenyl)sulfanylbenzene
CID:12853583
(3). FGI with cyanide gives 2-

cetonitrile
CID:12853584
(4). Alkali hydrolysis of the nitrile to 2-

cetic 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).

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