9359. Thioridazine

Nomenclature

CAS number: 50-52-2
10-[2-(1-Methyl-2-piperidinyl)ethyl]-2-(methylthio)-10H-phenothiazine; 2-methylmercapto-10-[2-(N-methyl-2-piperidyl)ethyl]phenothiazine; 3-methylmercapto-N-[2′-(N′-methyl-2-piperidyl)ethyl]phenothiazine.
C21H26N2S2; mol wt 370.57.
C 68.06%, H 7.07%, N 7.56%, S 17.31%.

Description and references

Dopamine receptor blocker; parent compound of sulforidazine and mesoridazine, q.q.v. Prepn: Bourquin et al., Helv. Chim. Acta 41, 1072 (1958). Toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Effect on dopaminergic function: D. M. Niedzwiecki et al., J. Pharmacol. Exp. Ther. 228, 636 (1984); C. D. Kilts et al., ibid. 231, 334 (1984). GLC determn in plasma: E. C. Dinovo et al., J. Pharm. Sci. 65, 667 (1976). HPLC sepn of isomers: R. Whelpton et al., J. Chromatogr. 426, 223 (1988). Clinical evaluation: R. Axelsson et al., Curr. Ther. Res. 21, 587 (1977). Comprehensive description: E. M. Abdel-Moety, K. A. Al-Rashood, Anal. Profiles Drug Subs. 18, 459-525 (1989).

Chemical structure

Properties

Crystals from acetone, mp 72-74°. bp0.02 230°. uv max (95% ethanol): 263, 314 nm (ε 38172, 4595); (0.1N HCl): 230, 263 nm (ε 20939, 45954); (0.1 N NaOH): 313 nm (ε 5226). pKa 9.5. Sol in alcohol (1 in 6), chloroform (1 in 0.81), ether (1 in 3); freely sol in dehydrated alcohol. Insol in water. LD50 orally in rats: 995 ±39 mg/kg (Goldenthal).

Derivative

Hydrochloride.

Nomenclature

CAS number: 130-61-0
TP-21; Aldazine (Alphapharm); Mellaril (Novartis); Melleretten (Novartis); Melleril (Novartis); Mallorol (Novartis); Novoridazine (Novopharm); Orsanil (Orion); Ridazin (Taro); Stalleril (Pharmacal).
C21H26N2S2.HCl; mol wt 407.04.
C 61.97%, H 6.69%, N 6.88%, S 15.76%, Cl 8.71%.

Properties

Crystals from acetone, mp 158-160°. uv max (water): 262, 310 nm (ε 41842, 3215); (95% ethanol): 264, 310 nm (ε 41598, 3256); (0.1N HCl): 264, 305 nm (ε 42371, 5495); (0.1N NaOH): 263 nm (ε 18392). Sol in water (1 in 9); freely sol in ethanol (1 in 10), methanol, chloroform (1 in 5). Insol in ether.

Therapeutic Category

Antipsychotic.

Keywords

Antipsychotic; Phenothiazines