Home > Name List By 9 > 9H-Thioxanthene-2-sulfonamide,N,N-dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]-

CAS No 5591-45-7 , 9H-Thioxanthene-2-sulfonamide,N,N-dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]-

  • Name: 9H-Thioxanthene-2-sulfonamide,N,N-dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]-
  • Synonyms: 2-(Dimethylsulfamoyl)-[9-(4-methyl-1-piperazinyl)propylidene]thioxanthene; CP12252-1; Navaron;N,N-Dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]thioxanthene-2-sulfonamide;NSC 108165; Navan; Orbinamon; Navane;Thioxanthene-2-sulfonamide,N,N-dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]- (7CI,8CI);9H-Thioxanthene-2-sulfonamide,N,N-dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]-; P 4657B;
  • CAS Registry Number:
  • Melting Point: 443.625
  • Flash Point: 316.1°C
  • Boiling Point: 599°Cat760mmHg
  • Density: 1.269g/cm3
  • Refractive index: 1.643
  • Safety Statements: Poison by ingestion. Moderately toxic by subcutaneous route. An experimental teratogen. Experimental reproductive effects. Human systemic effects hallucinations, distorted perceptions. When heated to decomposition it emits very toxic fumes of SOx and NOx.
  • Flash Point: 316.1°C
  • EINECS: 227-001-0
  • Molecular Weight: 443.67
  • InchiKey: GFBKORZTTCHDGY-UHFFFAOYSA-N
  • InChI: InChI=1S/C23H29N3O2S2/c1-24(2)30(27,28)18-10-11-23-21(17-18)19(20-7-4-5-9-22(20)29-23)8-6-12-26-15-13-25(3)14-16-26/h4-5,7-11,17H,6,12-16H2,1-3H3
  • Molecular Formula: C23H29 N3 O2 S2
  • Molecular Structure:CAS No:5591-45-7 9H-Thioxanthene-2-sulfonamide,N,N-dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]-

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References of 9H-Thioxanthene-2-sulfonamide,N,N-dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]-
Title: Thiothixene
CAS Registry Number: 5591-45-7
CAS Name: N,N-Dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]thioxanthene-2-sulfonamide
Synonyms: 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.