Thioproperazine

Thioproperazine

Clinical data
Trade names	Majeptil
ATC code	N05AB08 (WHO)
Identifiers
IUPAC name N,N-dimethyl-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine-2-carboxamide
CAS Number	316-81-4
PubChem CID	9429
DrugBank	DB01622
ChemSpider	9058
UNII	YJ050AQ56X
KEGG	D08585
ChEBI	CHEBI:59120
ChEMBL	ChEMBL609109
CompTox Dashboard (EPA)	DTXSID1023655
ECHA InfoCard	100.005.695
Chemical and physical data
Formula	C22H30N4O2S2
Molar mass	446.63 g·mol−1
3D 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,6,11-16H2,1-3H3 Key:VZYCZNZBPPHOFY-UHFFFAOYSA-N

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.

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 [137-47-3] (2) gives 4-(2-aminophenyl)sulfanyl-N,N-dimethyl-3-nitrobenzenesulfonamide [5510-56-5] (3). Sandmeyer reaction with cuprous bromide [7787-70-4] gave 4-[(2-Bromophenyl)-thio]-N,N'-dimethyl-3-nitro-benzenesulfonamide [5510-58-7] (4). Bechamp reduction gave 3-Amino-4-((2-bromophenyl)thio)-N,N-dimethylbenzenesulphonamide [5592-64-3] (5). Goldberg reaction completed the formation of the phenothiazine ring and gave N,N-dimethyl-10H-phenothiazine-2-sulfonamide [1090-78-4] (6). Attachment of the sidechain by sodamide reaction with 1-(3-Chloropropyl)-4-Methylpiperazine [104-16-5] (7) completes the synthesis of Thioproperazine (8), respectively.