Metitepine

Chemical compound From Wikipedia, the free encyclopedia

Metitepine

Metitepine (INNTooltip International Nonproprietary Name; developmental code names Ro 8-6837 (maleate), VUFB-6276 (mesylate)), also known as methiothepin, is a drug described as a "psychotropic agent" of the tricyclic or tetracyclic group which was never marketed.[1]

Quick Facts Clinical data, Other names ...
Metitepine
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Clinical data
Other namesMethiothepin; Methiothepine; Ro 8-6837 (maleate); VUFB-6276 (mesylate)
Identifiers
  • 1-methyl-4-(8-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepin-6-yl)piperazine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.261.496 Edit this at Wikidata
Chemical and physical data
FormulaC20H24N2S2
Molar mass356.55 g·mol−1
3D model (JSmol)
  • CN1CCN(CC1)C2Cc3ccccc3Sc4c2cc(cc4)SC
  • InChI=1S/C20H24N2S2/c1-21-9-11-22(12-10-21)18-13-15-5-3-4-6-19(15)24-20-8-7-16(23-2)14-17(18)20/h3-8,14,18H,9-13H2,1-2H3
  • Key:RLJFTICUTYVZDG-UHFFFAOYSA-N
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It acts as a non-selective antagonist of serotonin, dopamine, and adrenergic receptors, including of the serotonin 5-HT1, 5-HT2, 5-HT5, 5-HT6, and 5-HT7 receptors.[2][3][4][5][6] The drug has antipsychotic properties.[7]

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7 sources

Pharmacology

Pharmacodynamics

More information Target, Affinity (Ki, nM) ...
Metitepine binding profile
TargetAffinity (Ki, nM)Species
5-HT1A2.2–631Human
5-HT1B0.2–40Human
5-HT1D5.8–170Human
5-HT1E120–209Human
5-HT1F646–652Human
5-HT2A0.1–3.2Human
5-HT2B0.58–2.1Human
5-HT2C0.34–4.5Human
5-HT3≥3,000Rat
5-HT4NDND
5-HT5A1.0–32
100–126
29–146
Human
Mouse
Rat
5-HT5B16
29–145
Mouse
Rat
5-HT60.30–4.1Human
5-HT70.4–4.0Human
α1A0.06–7.9Guinea pig
α1B0.5Pig
D12.0Rat
D20.40Rat
Notes: The lower the affinity value, the more avidly the drug binds to the site. Refs: [2][3]
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Chemistry

Analogues

Metitepine is closely structurally related to certain other tetracyclic compounds including amoxapine, batelapine, clorotepine, clotiapine, clozapine, flumezapine, fluperlapine, loxapine, metiapine, olanzapine, oxyprothepin, perathiepin, perlapine, quetiapine, tampramine, and tenilapine.

Synthesis

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Synthesis:[8][9][10]

The reduction of 2-(4-methylsulfanylphenyl)sulfanylbenzoic acid, CID:2733664 (1) gives [2-(4-methylsulfanylphenyl)sulfanylphenyl]methanol, CID:12853582 (2). Halogenating with thionyl chloride gives 1-(chloromethyl)-2-(4-methylsulfanylphenyl)sulfanylbenzene, CID:12853583 (3). FGI with cyanide gives 2-[2-(4-methylsulfanylphenyl)sulfanylphenyl]acetonitrile, CID:12853584 (4). Alkali hydrolysis of the nitrile to 2-[2-(4-methylsulfanylphenyl)sulfanylphenyl]acetic acid, CID:12383832 (5). PPA cyclization to 3-methylsulfanyl-6H-benzo[b][1]benzothiepin-5-one, CID:827052 (6). The reduction with sodium borohydride gives 3-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepin-5-ol, CID:13597048 (7). Halogenating with a second round of thionyl chloride gives 5-chloro-3-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepine, CID:12404411. Alkylation with 1-methylpiperazine [109-01-3] completed the synthesis of Metitepine (9).

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References

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