View source for Thioxanthene

{{Chembox
| Verifiedfields = changed
| verifiedrevid = 470609193
| ImageFile = Thioxanthene.png
| ImageSize = 200px
| PIN = 9''H''-Thioxanthene<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=213 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| OtherNames = 10''H''-Dibenzo[''b'',''e'']thiin
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 60819
| InChI = 1/C13H10S/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2
| InChIKey = PQJUJGAVDBINPI-UHFFFAOYAP
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 79451
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H10S/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-8H,9H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PQJUJGAVDBINPI-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 261-31-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1J3P67894A
| PubChem = 67495
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 51055
| SMILES = S2c1ccccc1Cc3c2cccc3
}}
|Section2={{Chembox Properties
| C=13 | H=10 | S=1
| Appearance = 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility = 
  }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = 
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}}

'''Thioxanthene''' is a [[chemical compound]] in which the [[oxygen]] atom in [[xanthene]] is replaced with a [[sulfur]] atom. It is also related to [[phenothiazine]]. Several of its [[chemical derivative|derivative]]s are used as [[typical antipsychotic]]s in the treatment of [[schizophrenia]] and other [[psychosis|psychose]]s.

== Derivatives ==

The derivatives of thioxanthene used clinically as antipsychotics include:

* [[Chlorprothixene]] (Cloxan, Taractan, Truxal)
* [[Clopenthixol]] (Sordinol)
* [[Flupenthixol]] (Depixol, Fluanxol)
* [[Thiothixene]] (Navane)
* [[Zuclopenthixol]] (Cisordinol, Clopixol, Acuphase)

The therapeutic efficacy of these drugs is related to their ability to [[receptor_antagonist|antagonize]] the [[D2 receptor|D<sub>2</sub> receptor]]s in the brain, though they have actions at other sites such as [[serotonin receptor|serotonin]], [[adrenergic receptor|adrenaline]], and [[histamine|histamine receptor]]s as well which mostly contribute to [[side effect]]s.

The thioxanthenes, as a class, are closely related chemically to the [[phenothiazines]]. 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.<ref>''[[Goodman & Gilman's The Pharmacological Basis of Therapeutics]]''</ref> 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 ==
{{Reflist|2}}

== External links ==
* {{MeshName|Thioxanthenes}}
* [https://www.nlm.nih.gov/medlineplus/druginfo/uspdi/202564.html MedlinePlus]

{{Antipsychotics}}
{{Antiemetics}}
{{Sedatives}}
{{Adrenergics}}
{{Dopaminergics}}
{{Histaminergics}}
{{Serotonergics}}
{{Tricyclics}}

[[Category:Thioxanthenes| ]]