Thiothixene
Title: Thiothixene
CAS Registry Number: 5591-45-7
CAS Name: N,N-Dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]thioxanthene-2-sulfonamide
Additional Names: cis9-[3-(4-methyl-1-piperazinyl)propylidene]-2-(dimethylsulfonamido)thioxanthene; tiotixene
Trademarks: Navane (Roerig); Orbinamon (Pfizer)
Molecular Formula: C23H29N3O2S2
Molecular Weight: 443.63
Percent Composition: C 62.27%, H 6.59%, N 9.47%, O 7.21%, S 14.46%
Literature References: Prepn of cis/trans-isomer mixture and sepn of isomers: Bloom, Muren, BE 647066 corresp to US 3310553 (1964, 1967 both to Pfizer); Muren, Bloom, J. Med. Chem. 13, 17 (1970). Only cis-isomer exhibits therapeutic activity. Structure studies: J. P. Schaefer, Chem. Commun. 1967, 743. Pharmacological studies: A. Weissman, Psychopharmacologia 12, 142 (1968). HPLC determn in serum: C. Dilger et al., Arzneim.-Forsch. 38, 1522 (1988). Book: T. A. Ban, Psychopharmacology of Thiothixene (Raven Press, New York, 1978) 485 pp. Comprehensive description: D. K. Wyatt, L. T. Grady, Anal. Profiles Drug Subs. 18, 527-565 (1989).
 
Derivative Type: cis-Isomer
Properties: Crystals, mp 147.5-149°. uv max (methanol): 228, 260, 310 nm (log e 4.6, 4.3, 3.9). Has greater pharmacologic activity than trans-isomer. LD50 in mice, rats (mg/kg): 100, 55 i.p. (Weissman).
Melting point: mp 147.5-149°
Absorption maximum: uv max (methanol): 228, 260, 310 nm (log e 4.6, 4.3, 3.9)
Toxicity data: LD50 in mice, rats (mg/kg): 100, 55 i.p. (Weissman)
 
Derivative Type: trans-Isomer
Properties: mp 123-124.5°. uv max (methanol): 229, 252, 301 nm (log e 4.5, 4.2, 3.9). LD50 i.p. in mice: 235 mg/kg (Weissman).
Melting point: mp 123-124.5°
Absorption maximum: uv max (methanol): 229, 252, 301 nm (log e 4.5, 4.2, 3.9)
Toxicity data: LD50 i.p. in mice: 235 mg/kg (Weissman)
 
Derivative Type: cis-trans-Isomer mixture
Properties: Crystals, mp 114-118°.
Melting point: mp 114-118°
 
Derivative Type: Dimaleate
Properties: mp 158-160.5°.
Melting point: mp 158-160.5°
 
Derivative Type: Dioxalate
Properties: mp 229°.
Melting point: mp 229°
 
Therap-Cat: Antipsychotic.
Keywords: Antipsychotic; Thioxanthenes.

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