103002-96-6

Basic information

• Product Name: [6-(4-Hydroxy-4-phenyl-piperidin-1-yl)-dibenzo[b,e]azepin-(11E)-ylidene]-acetonitrile
• CAS NO: 103002-96-6
• Molecular Weight: 405.499
• Mol File: 103002-96-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [6-(4-Hydroxy-4-phenyl-piperidin-1-yl)-dibenzo[b,e]azepin-(11E)-ylidene]-acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: [6-(4-Hydroxy-4-phenyl-piperidin-1-yl)-dibenzo[b,e]azepin-(11E)-ylidene]-acetonitrile(103002-96-6)
• EPA Substance Registry System: [6-(4-Hydroxy-4-phenyl-piperidin-1-yl)-dibenzo[b,e]azepin-(11E)-ylidene]-acetonitrile(103002-96-6)

Safety Data

• Hazardous Substances Data: 103002-96-6(Hazardous Substances Data)

Upstream product

• 77042-87-6 (E),(Z)-(5,6-dihydro-11H-dibenzazepin-6-on-11-ylidene)acetonitrile 
• 1143-50-6 5,6-dihydro-6,11-dioxomorphanthridine 

Relevant articles and documents

Tricyclic epines. Novel (E)- and (Z)-11H-dibenz[b,e]azepines as potential central nervous system agents. Variation of the basic side chain

The synthesis and pharmacological activity of new (E),(Z)-[6-(alkylamino)-11H-dibenz[b,e]azepin-11-ylidene]- acetonitriles 12-45 and (E),(Z)-[6-(aminoalkoxy)-11H-dibenz[b,e]azepine-11-ylidene]acetonitriles 46-51 are described. The introduction of the cyanomethylene group into the 11-position of the 11H-dibenz[b,e]azepine framework has been carried out by a Wittig-Horner reaction under mild conditions. The (E),(Z) isomers were separated by fractional crystallization, assignment being achieved by X-ray analysis. A number of (E),(Z)-[6-(alkylamino)-11H-dibenz[b,e]azepin-11-ylidene]acetonitriles (12, 14, 16, 20) show potent neuroleptic activity (2-7 times that of clozapine) in animal tests. The screening included tests for sedative and anticholinergic activity in mice, apomorphine and tryptamine antagonism in rats, and muscle-relaxing activity in rabbits. The divergence in the activity profile in the case of the separated (E),(Z) isomers has been observed as an interesting new aspect: the (Z) isomers show a significantly higher sedative and muscle-relaxant activity, whereas the (E) isomers possess a higher anticholinergic efficacy and somewhat greater apomorphine antagonism. Broad changes in the basic side chain were made in order to investigate structure-activity relationships. The important geometrical parameters for the molecules, obtained by X-ray analysis, were compared with the corresponding features in dopamine agonists and antagonists.