thioproperazine thioproperazine thioproperazine, sold under the brand name majeptil, is a typical antipsychotic of the phenothiazine group which is used as a tranquilizer, antiemetic, sedative, and in the treatment of schizophrenia and manic phase of bipolar disorder. majeptil is available in 10 mg tablets. thioproperazineclinical datatrade namesmajeptilatc coden05ab08 (who) identifiers iupac name n,n-dimethyl-10--10h-phenothiazine-2-carboxamide cas number316-81-4pubchem cid9429drugbankdb01622chemspider9058uniiyj050aq56xkeggd08585chebichebi:59120chemblchembl609109comptox dashboard (epa)dtxsid1023655 echa infocard100.005.695 chemical and physical dataformulac22h30n4o2s2molar mass446.63 g·mol−13d model (jsmol)interactive image smiles cn1ccn(cc1)cccn2c3=cc=cc=c3sc4=c2c=c(c=c4)s(=o)(=o)n(c)c inchi inchi=1s/c22h30n4o2s2/c1-23(2)30(27,28)18-9-10-22-20(17-18)26(19-7-4-5-8-21(19)29-22)12-6-11-25-15-13-24(3)14-16-25/h4-5,7-10,17h,6,11-16h2,1-3h3key:vzycznzbpphofy-uhfffaoysa-n side effects common extrapyramidal symptoms amenorrhea decreased sexual interest and/or function swelling of breasts and milk production in males and females difficulty sleeping constipation reduced amount of urine dizziness drowsiness dry mouth nausea headache weight changes rare but potentially serious adverse effects agranulocytosis neuroleptic malignant syndrome (nms) sudden cardiac death torsades de pointes elderly individuals with dementia-related psychosis treated with antipsychotic medication are at an increased risk of death compared to individuals not receiving antipsychotics. drug interactions medications for allergies (e.g., benadryl diphenhydramine), certain medications for sleep (e.g., lorazepam, zopiclone), certain medications for pain (e.g., fentanyl), and antiparkinson medications can increase the sedative effect of thioproperazine and can be potentially dangerous when used together. synthesis thieme synthesis: patents (ex 3): thioether formation between 2-aminothiophenol (1) and 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide (2) gives 4-(2-aminophenyl)sulfanyl-n,n-dimethyl-3-nitrobenzenesulfonamide (3). sandmeyer reaction with cuprous bromide gave 4--n,n'-dimethyl-3-nitro-benzenesulfonamide (4). bechamp reduction gave 3-amino-4-((2-bromophenyl)thio)-n,n-dimethylbenzenesulphonamide (5). goldberg reaction completed the formation of the phenothiazine ring and gave n,n-dimethyl-10h-phenothiazine-2-sulfonamide (6). attachment of the sidechain by sodamide reaction with 1-(3-chloropropyl)-4-methylpiperazine (7) completes the synthesis of thioproperazine (8), respectively.