thiethylperazine thiethylperazine thiethylperazine (torecan, norzine) is an antiemetic of the phenothiazine class. it is an antagonist of dopamine receptors (drd1, drd2, drd4) as well as of 5-ht2a, 5-ht2c receptors, machrs (1 through 5), α1 adrenergic receptor and h1 receptor. thiethylperazineclinical datatrade namestorecan, norzineahfs/drugs.commicromedex detailed consumer informationatc coder06ad03 (who) pharmacokinetic dataprotein binding60%identifiers iupac name 2-(ethylthio)-10--10h-phenothiazine cas number1420-55-9 ypubchem cid5440iuphar/bps7306drugbankdb00372 ychemspider5245 yunii8etk1waf6rkeggd02354 ychebichebi:9544 ychemblchembl1378 ycomptox dashboard (epa)dtxsid1023651 echa infocard100.014.381 chemical and physical dataformulac22h29n3s2molar mass399.62 g·mol−13d model (jsmol)interactive image smiles s(c2cc1n(c3c(sc1cc2)cccc3)cccn4ccn(c)cc4)cc inchi inchi=1s/c22h29n3s2/c1-3-26-18-9-10-22-20(17-18)25(19-7-4-5-8-21(19)27-22)12-6-11-24-15-13-23(2)14-16-24/h4-5,7-10,17h,3,6,11-16h2,1-2h3 ykey:xctylcdetuvoip-uhfffaoysa-n y (verify) thiethylperazine activates the transport protein abcc1 that clears beta-amyloid from brains of mice. pharmacokinetics distribution this drug is highly lipofilic and it binds with membranes and serum proteins (over 85%). it accumulates in organs with high blood flow and penetrates the placenta. it cannot be removed with dialysis. metabolism it is mainly metabolised in the liver and only 3% is eliminated unchanged. torecan's half-life is 12 h. teratogenicity in toxic doses above the terapeutic window, it increases the rate of cleft palate occurrence. antypsychotic activity theithylperazine may possess antypsychotic activity due to the antagonism of 5-ht2 and d2 receptors. because of this, it would not cause extrapyramidal symptoms. nevertheless, it was never marketed as such drug. one cause of acute dystonia occurred in a 19-year-old male patient after discontinuation of this drug. overdose signs of acute thiethylperazine overdose include: extrapyramidal symptoms, confusion, convulsions, respiratory depression and hypotension. synthesis thieme synthesis: patent: goldberg reaction between 3-(ethylsulfanyl)aniline (1) and 2-chlorobenzoic acid (2) to give the diarylamine, cid:82254530 (3). the carboxyl in the anthranilic acid residue, having performed its activating function, is then thermolytically removed to form (4). upon treatment with sulfur and iodine, we get predominantly the phenothiazine (5); the rxn may well be aided by the presence of the electron donating thioether at the para-position. alkylation with 1-(ɣ̞-chloropropyl)-4-methylpiperazine (6) in the presence of sodamide affords thiethylperazine (7).