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Metitepine (; developmental code names Ro 8-6837 ( maleate), VUFB-6276 ( mesylate)), also known as methiothepin, is a
The reduction of 2-(4-methylsulfanylphenyl)sulfanylbenzoic acid
CID:2733664
(1) gives
CID:12853582
(2). Halogenating with thionyl chloride gives 1-(chloromethyl)-2-(4-methylsulfanylphenyl)sulfanylbenzene
CID:12853583
(3). FGI with cyanide gives 2-
CID:12853584
(4). Alkali hydrolysis of the nitrile to 2-
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).
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
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 group which was never marketed. It acts as a non-selective 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 properties.
Synthesis
The reduction of 2-(4-methylsulfanylphenyl)sulfanylbenzoic acidCID: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. ...
ethanolCID:12853582
(2). Halogenating with thionyl chloride gives 1-(chloromethyl)-2-(4-methylsulfanylphenyl)sulfanylbenzene
CID:12853583
(3). FGI with cyanide gives 2-
-(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. ...
cetonitrileCID:12853584
(4). Alkali hydrolysis of the nitrile to 2-
-(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. ...
cetic acidCID: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