Thiethylperazine

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Thiethylperazine
Thiethylperazine structure.png
Systematic (IUPAC) name
2-(ethylthio)-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Legal status
?
Pharmacokinetic data
Protein binding 60%
Identifiers
CAS number 1420-55-9 YesY
ATC code R06AD03
PubChem CID 5440
DrugBank DB00372
ChemSpider 5245 YesY
UNII 8ETK1WAF6R YesY
KEGG D02354 YesY
ChEBI CHEBI:9544 YesY
ChEMBL CHEMBL1378 YesY
Chemical data
Formula C22H29N3S2 
Molecular mass 399.618 g/mol
 YesY (what is this?)  (verify)

Thiethylperazine (Torecan) is an antiemetic of the phenothiazine class. Though it was never licensed or used as an antipsychotic, it may have such effects.

Synthesis[edit]

Thiethylperazine synthesis:[1]

The nitrogen in 3-(ethylsulfanyl)aniline (1) displaces the chlorine in 2-chlorobenzoic acid (2) to give the diarylamine (3). The carboxyl in the anthranilic acid residue, having performed its activating function, is then thermolytically removed to form (4). This gives predominantly the phenothiazine on treatment with sulfur and iodine; The rxn may well be aided by the presence of the electron donating thioether at the para-position. Alkylation of the anion again via its anion, with 1-(ɣ̞-chloropropyl)-4-methylpiperazine (5) affords thiethylperazine (6).

Alzheimer[edit]

Thiethylperazine activates the transport protein ABCC1 that clears beta-amyloid from brains of mice. [2]

See also[edit]

References[edit]

  1. ^ Bourquin, J. -P.; Schwarb, G.; Gamboni, G.; Fischer, R.; Ruesch, L.; Guldimann, S.; Theus, V.; Schenker, E.; Renz, J. (1958). "Synthesen auf dem Phenothiazin-Gebiet. 2. Mitteilung. N-substituierte Mercaptophenothiazin-Derivate". Helvetica Chimica Acta 41 (4): 1072. doi:10.1002/hlca.19580410420.  edit
  2. ^ Science Daily (September 1, 2011). "Alzheimer Disease: Transport Protein ABCC1 Plays Key Role in Clearing Beta-Amyloid from Brains of Mice.". Retrieved September 1, 2011.