26615-21-4

Basic information

• Product Name: ZOTEPINE
• Synonyms: ZOTEPINE;2-((8-chlorodibenzo(b,f)thiepin-10-yl)oxy)-n,n-dimethylethanamine;2-chlor-11-(2-dimethylaminoaethoxy)-dibenzo(b,f)-thiepin;2-chloro-11-(2-(dimethylamino)ethoxy)dibenzo(b,f)thiepin;2-chloro-11-(2-dimethylaminoethoxy)-dibenzo(b,f)thiepine;f)thiepin,2-chloro-11-(2-(dimethylamino)ethoxy)-dibenzo(;lodopin;zotepina
• CAS NO: 26615-21-4
• Molecular Formula: C₁₈H₁₈ClNOS
• Molecular Weight: 331.86
• Product Categories: Pharmaceutical intermediate
• Mol File: 26615-21-4.mol

Chemical Properties

• Melting Point: 90-91°
• Boiling Point: 478.449 °C at 760 mmHg
• Flash Point: 243.157 °C
• Appearance: white to off-white/
• Density: 1.0675 (rough estimate)
• Vapor Pressure: 2.57E-09mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• Storage Temp.: Store at RT
• Solubility: DMSO: ≥20mg/mL
• PKA: 8.72±0.28(Predicted)
• CAS DataBase Reference: ZOTEPINE(CAS DataBase Reference)
• NIST Chemistry Reference: ZOTEPINE(26615-21-4)
• EPA Substance Registry System: ZOTEPINE(26615-21-4)

Safety Data

• Hazard Codes: T
• Statements: 25-50/53
• Safety Statements: 45-60-61
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 26615-21-4(Hazardous Substances Data)

Usage

Chemical Properties

White to off white crystalline powder

Originator

Lodopin,Fujisawa Pharmaceutical,Japan,1982

Manufacturing Process

A suspension of 30 g of sodium hydride in benzene (30 ml) was added dropwise to 52 g of 8-chlorodibenzo[b,f]thiepin-10(11H)-one dissolved in dimethylformamide (800 ml), and the mixture was heated at 100°C for 2 hours. To this, there were added 68 g of 2-dimethylaminoethyl chloride, and the mixture was heated at 60°C for 39 hours. The reaction mixture, after cooled, was poured into ice-water, and the solution was extracted with ethyl acetate. The ethyl acetate layer, after washed with water, was extracted with 10% hydrochloric acid, when oil was precipitated. The aqueous layer, in which oil was precipitated, was washed with ether, made neutral with concentrated sodium hydroxide solution and then extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate, and concentrated to give oil, which was allowed to stand to provide solid. The solid was washed with petroleum ether and recrystallized from cyclohexane to yield 42.5 g of 8-chloro-10-(2-dimethylaminoethyl)-oxydibenzo[b,f]thiepin as crystals, melting point 90°C to 91°C. Maleate as colorless needle, melting point 204°C to 204.5°C.

Therapeutic Function

Tranquilizer

InChI:InChI=1/C18H18ClNOS/c1-20(2)9-10-21-16-11-13-5-3-4-6-17(13)22-18-8-7-14(19)12-15(16)18/h3-8,11-12H,9-10H2,1-2H3

Upstream product

• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Relevant articles and documents

Synthesis and oxidant properties of phase 1 benzepine N-oxides of common antipsychotic drugs

There is increasing evidence that cell constituents are oxidized by widely used antipsychotic drugs but until now the underlying chemistry has remained unclear. It is well known that such drugs readily undergo N-oxidation as a first key metabolic step. To gain insight into the problem, the tertiary phase 1 N-oxides of clozapine, olanzapine, quetiapine, and zotepine were synthesized, together with the N,S-dioxides of quetiapine and zotepine. These N-oxides were then subjected to well-established chemical transformations to test their oxidant properties in group VIII transition-metal-catalyzed reactions. In the osmium tetroxide catalyzed dihydroxylation of styrene or cinnamyl alcohol and in the tetrapropylammonium perruthenate catalyzed oxidation of cinnamyl alcohol, the benzepine N-oxides could be used as replacements for the standard oxidant, N-methylmorpholine N-oxide (NMO) with varying degrees of efficiency. From a chemical point of view, clozapine N-oxide displayed a comparable oxidation power to NMO, characterizing the benzepines as oxygen carriers. Moreover, quetiapine was found to be an excellent double oxygen acceptor, undergoing initial N-oxidation and subsequent S-oxidation. It is therefore worthwhile considering whether oxidative damage to the human body might be related to the potential redox properties of common antipsychotic drugs. Georg Thieme Verlag Stuttgart ? New York.

Combination treatment for anxiety, depression, obsessive compulsive disorder and psychosis

The present invention relates to a method of treating depression, obsessive compulsive disorder and psychosis in a mammal, including a human, by administering to the mammal an atypical antipsychotic in combination with an antidepressant agent with improvement in efficiency. It also relates to pharmaceutical compositions containing a pharmaceutically acceptable carrier, an atypical antipsychotic, and an SRI.