Thioproperazine Explained

Drug Name:Thioproperazine
Width:240
Tradename:Majeptil
Atc Prefix:N05
Atc Suffix:AB08
Legal Br:C1
Legal Br Comment:[1]
Cas Number:316-81-4
Pubchem:9429
Drugbank:DB01622
Chemspiderid:9058
Unii:YJ050AQ56X
Kegg:D08585
Chebi:59120
Chembl:609109
Iupac Name:N,N-dimethyl-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine-2-carboxamide
C:22
H:30
N:4
O:2
S:2
Smiles:CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)S(=O)(=O)N(C)C
Stdinchi: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
Stdinchikey: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.[2] [3] [4] [5] Majeptil is available in 10 mg tablets.[6]

Side effects

Common[7]

Rare but potentially serious adverse effects

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

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.

Notes and References

  1. Web site: Anvisa . Brazilian Health Regulatory Agency . 2023-03-31 . RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial . Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control. live . https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 . 2023-08-03 . 2023-08-16 . . pt-BR . 2023-04-04.
  2. Book: Index Nominum 2000: International Drug Directory. 2000. Taylor & Francis. 978-3-88763-075-1. 1019–.
  3. Book: Morton IK, Hall JM . Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 6 December 2012. Springer Science & Business Media. 978-94-011-4439-1. 272–.
  4. Web site: Phenothiazines (Systemic) . Drugs.com .
  5. Web site: Thioproperazine - Oral . en-US. 2018-09-16.
  6. Web site: Thioproperazine. www.drugbank.ca. 2018-09-16.
  7. Web site: Schizophrenia Society of Ontario - Majeptil (thioproperazine). www.schizophrenia.on.ca. 2018-09-16.