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 names	Artalan, Dartal, Dartalan, Dartan
ATC code	N05AB05 (WHO)
Identifiers
IUPAC name 2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethyl acetate
CAS Number	84-06-0 Y
PubChem CID	6762
ChemSpider	6504 Y
UNII	0JFY081Q2X
KEGG	D09216 Y
ChEBI	CHEBI:59119 Y
ChEMBL	ChEMBL1697851
CompTox Dashboard (EPA)	DTXSID6023654
ECHA InfoCard	100.001.376
Chemical and physical data
Formula	C23H28ClN3O2S
Molar mass	446.01 g·mol−1
3D model (JSmol)	Interactive image
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
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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

• Typical antipsychotic
• Phenothiazine