9356. Thiopropazate

Nomenclature

CAS number: 84-06-0
4-[3-(2-Chlorophenothiazin-10-yl)propyl]-1-piperazineethanol acetate; 2-chloro-10-[3-[1-(2-acetoxyethyl)-4-piperazinyl]propyl]phenothiazine; 10-[3-[1-(2-acetoxyethyl)-4-piperazinyl]propyl]-2-chlorophenothiazine; N-(β-acetoxyethyl)-N′-[γ-(2′-chloro-10′-phenothiazinyl)propyl]piperazine; 1-(2-acetoxyethyl)-4-[3-(2-chloro-10-phenothiazinyl)propyl]piperazine.
C23H28ClN3O2S; mol wt 446.01.
C 61.94%, H 6.33%, Cl 7.95%, N 9.42%, O 7.17%, S 7.19%.

Description and references

Prepd from 2-chloro-10-(γ-chloropropyl)phenothiazine and piperazine in butanone followed by treatment with β-bromoethyl acetate in toluene: Cusic, US 2766235 (1956); Anderson et al., Arzneim.-Forsch. 12, 937 (1962).

Chemical structure

Properties

Free base, bp0.1 214-218°. Sol in ether.

Derivative

Dihydrochloride.

Nomenclature

CAS number: 146-28-1
Dartal (Searle); Dartalan (Searle).
C23H28ClN3O2S.2HCl; mol wt 518.93.
C 53.23%, H 5.83%, Cl 20.50%, N 8.10%, O 6.17%, S 6.18%.

Properties

Crystals from 95% ethanol, dec 223-229°. Freely sol in water; much less sol in alc, chloroform; almost insol in ether.

Derivative

Dimaleate.

Nomenclature

CAS number: 104999-18-0
C23H28ClN3O2S.2C4H4O4; mol wt 678.15.
C 54.90%, H 5.35%, Cl 5.23%, N 6.20%, O 23.59%, S 4.73%.

Properties

Crystals from methanol + ethanol, mp 167-169°.

Therapeutic Category

Antipsychotic.

Keywords

Antipsychotic; Phenothiazines