2188. Chlorprothixene

Nomenclature

CAS number: 113-59-7
(Z)-3-(2-Chloro-9H-thioxanthen-9-ylidene)-N,N-dimethyl-1-propanamine; (Z)-2-chloro-N,N-dimethylthioxanthene-Δ9,γ-propylamine; cis-2-chloro-N,N-dimethyl-3-thioxanthen-9-ylidenepropylamine; α-2-chloro-10-(3-dimethylaminopropylidene)thiaxanthene; N-714; Taractan (Roche); Tarasan (Roche); Truxal (Lundbeck); Truxaletten (Lundbeck).
C18H18ClNS; mol wt 315.86.
C 68.45%, H 5.74%, Cl 11.22%, N 4.43%, S 10.15%.

Description and references

Prepn: GB 829763; E. L. Engelhardt, US 3046283 (1960, 1962 both to Merck & Co.). Structure-activity study: G. E. Bonvicino et al., J. Org. Chem. 26, 2383 (1961). Comprehensive description: B. C. Rudy, B. Z. Senkowski, Anal. Profiles Drug Subs. 2, 63-84 (1973). HPLC determn in serum: M. Bagli et al., J. Chromatogr. B 657, 141 (1994). Clinical pharmacokinetics: idem et al., Arzneim.-Forsch. 46, 247 (1996).

Chemical structure

Properties

Pale yellow crystals, mp 97-98°. Practically insol in water; sol in alcohol, ether, chloroform. Incompatible with acids, alkalies, phenobarbital, thiopental sodium, mepazine.

Derivative

Hydrochloride.

Nomenclature

CAS number: 6469-93-8
C18H18ClNS.HCl; mol wt 352.32.
C 61.36%, H 5.44%, Cl 20.13%, N 3.98%, S 9.10%.

Properties

Crystals, mp 221°. Freely sol in water at pH 6 to 6.5.

Therapeutic Category

Antipsychotic.

Keywords

Antipsychotic; Thioxanthenes