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Thioxanthene

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Thioxanthene
Names
Preferred IUPAC name
9H-Thioxanthene[1]
Other names
10H-Dibenzo[b,e]thiin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.430Edit this at Wikidata
UNII
  • InChI=1S/C13H10S/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2checkY
    Key: PQJUJGAVDBINPI-UHFFFAOYSA-NcheckY
  • InChI=1/C13H10S/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2
    Key: PQJUJGAVDBINPI-UHFFFAOYAP
  • S2c1ccccc1Cc3c2cccc3
Properties
C13H10S
Molar mass 198.28g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Thioxantheneis achemical compoundin which theoxygenatom inxantheneis replaced with asulfuratom. It is also related tophenothiazine.Several of itsderivativesare used astypical antipsychoticsin the treatment ofschizophreniaand otherpsychoses.

Derivatives

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The derivatives of thioxanthene used clinically as antipsychotics include:

The therapeutic efficacy of these drugs is related to their ability toantagonizetheD2receptorsin the brain, though they have actions at other sites such asserotonin,adrenaline,andhistamine receptorsas well which mostly contribute toside effects.

The thioxanthenes, as a class, are closely related chemically to thephenothiazines.The major structural difference is that the nitrogen at position 10 in the phenothiazines is replaced by a carbon atom with a double bond to the side chain.[2]This difference is noted in the illustration of flupenthixol, which shows a double-bonded carbon in the number 10 position (opposite the sulfur molecule in the central chain).

References

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  1. ^International Union of Pure and Applied Chemistry(2014).Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013.The Royal Society of Chemistry.p. 213.doi:10.1039/9781849733069.ISBN978-0-85404-182-4.
  2. ^Goodman & Gilman's The Pharmacological Basis of Therapeutics
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