Thiopropazate

Thiopropazate (Artalan, Dartal, Dartalan, Dartan) is a typical antipsychotic of the phenothiazine class.[1] It is a prodrug to perphenazine.

Thiopropazate
Clinical data
Trade namesArtalan, Dartal, Dartalan, Dartan
ATC code
Identifiers
IUPAC name
  • 2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethyl acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.376
Chemical and physical data
FormulaC23H28ClN3O2S
Molar mass446.01 g·mol−1
3D model (JSmol)
SMILES
  • CC(=O)OCCN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)Cl
InChI
  • InChI=1S/C23H28ClN3O2S/c1-18(28)29-16-15-26-13-11-25(12-14-26)9-4-10-27-20-5-2-3-6-22(20)30-23-8-7-19(24)17-21(23)27/h2-3,5-8,17H,4,9-16H2,1H3 Y
  • Key:AIUHRQHVWSUTGJ-UHFFFAOYSA-N Y
  (verify)

Thiopropazate is manufactured by Searle (US, UK) & Boehringer Mannheim (Germany)[2] Thiopropazate is sold by Chembase, AAA Chemistry, ZINC, AKos Consulting & Solutions, Boc Sciences, ChemFrog, and ChemMol[3]

Synthesis
Thieme Patent:[4]

The alkylation of 2-chloro-10-(3-chloropropyl)phenothiazine [2765-59-5] (1) with Piperazine (2) gives N-Desmethylprochlorperazine [40323-85-1] (3). Further alkylation with 2-Bromoethyl acetate [927-68-4] (4) gives Thiopropazate (5).

See also

References
  1. Buckingham J (1996). Dictionary of organic compounds. London: Chapman & Hall. p. 5148. ISBN 0-412-54090-8.
  2. Pharmaceutical Manufacturing Encyclopedia p. 3209
  3. "Thiopropazate". PubChem. United States Library of Medicine.
  4. John W Cusic, U.S. Patent 2,766,235 (1956 to Searle & Co).


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