21636-40-8

Basic information

• Product Name: 11-Piperazinyldibenz[b,f][1,4]oxazepine
• Synonyms: 11-Piperazinyldibenz[b,f][1,4]oxazepine;Dibenz[b,f][1,4]oxazepine, 11-(1-piperazinyl)-;6-(1-piperazinyl)benzo[b][1,5]benzoxazepine;6-piperazin-1-ylbenzo[b][1,5]benzoxazepine
• CAS NO: 21636-40-8
• Molecular Formula: C17H17N3O
• Molecular Weight: 279.34
• Mol File: 21636-40-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Density: 1.27
• CAS DataBase Reference: 11-Piperazinyldibenz[b,f][1,4]oxazepine(CAS DataBase Reference)
• NIST Chemistry Reference: 11-Piperazinyldibenz[b,f][1,4]oxazepine(21636-40-8)
• EPA Substance Registry System: 11-Piperazinyldibenz[b,f][1,4]oxazepine(21636-40-8)

Safety Data

• Hazardous Substances Data: 21636-40-8(Hazardous Substances Data)

Usage

Description

11-Piperazinyldibenz[b,f][1,4]oxazepine, also known as 11-(1-Piperazinyl)dibenz[b,f][1,4]oxazepine, is a chemical compound that serves as a metabolite of Loxapine. It is characterized by its complex molecular structure, which includes a dibenzoxazepine core fused with a piperazine ring. 11-Piperazinyldibenz[b,f][1,4]oxazepine has been found to possess significant pharmacological properties, making it a valuable substance in the field of medicine.

Uses

Used in Pharmaceutical Industry:
11-Piperazinyldibenz[b,f][1,4]oxazepine is used as an active pharmaceutical ingredient for the treatment of neuropsychiatric diseases. Its application in this field is due to its ability to modulate various neurotransmitter systems in the brain, which can help alleviate symptoms associated with these conditions.
Used in Research and Development:
In addition to its therapeutic applications, 11-Piperazinyldibenz[b,f][1,4]oxazepine is also utilized in research and development for the study of neuropsychiatric diseases and the development of new drugs targeting these conditions. Its unique chemical structure and pharmacological properties make it a valuable tool for understanding the underlying mechanisms of these diseases and for designing more effective treatments.
Used in Drug Metabolism Studies:
As a metabolite of Loxapine, 11-Piperazinyldibenz[b,f][1,4]oxazepine plays a crucial role in drug metabolism studies. Understanding the metabolic pathways and the effects of this compound can help researchers optimize drug dosages, minimize side effects, and improve the overall safety and efficacy of Loxapine and other related medications.

Upstream product

• 110-85-0 piperazine 
• 3158-85-8 10H-dibenzo[b,f][1,4]oxazepin-11-one 
• 88-73-3 2-Chloronitrobenzene 
• 666818-15-1 2-fluoro-N-(2-hydroxyphenyl)-benzamide 
• 95-55-6 2-amino-phenol 
• 445-29-4 o-fluoro-benzoic acid 
• 119-36-8 methyl salicylate 
• 1493-27-2 ortho-nitrofluorobenzene 
• 171103-28-9 2-amino-2'-methyl diphenyl ether carboxylate 
• 92164-06-2 2-nitro-2'-methyl diphenyl ether carboxylate 
• 62469-61-8 11-chloro-dibenz<1,4>oxazepine 

Relevant articles and documents

Dibenzo[b,f][1,4]oxazepines and dibenzo[b,e]oxepines: Influence of the chlorine substitution pattern on the pharmacology at the H1R, H4R, 5-HT2AR and other selected GPCRs

Inspired by VUF6884 (7-Chloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepine), reported as a dual H1/H4 receptor ligand (pKi: 8.11 (human H1R (hH1R)), 7.55 (human H4R (hH4R))), four known and 28 new oxazepine and related oxepine derivatives were synthesised and pharmacologically characterized at histamine receptors and selected aminergic GPCRs. In contrast to the oxazepine series, within the oxepine series, the new compounds showed high affinity to the hH1R (pKi: 6.8–8.7), but no or moderate affinity to the hH4R (pKi: ≤ 5.3). For one oxepine derivative (1-(2-Chloro-6,11-dihydrodibenzo[b,e]oxepin-11-yl)-4-methylpiperazine), the enantiomers were separated and the R-enantiomer was identified as the eutomer at the hH1R (pKi: 8.83 (R), 7.63 (S)) and the guinea-pig H1R (gpH1R) (pKi: 8.82 (R), 7.41 (S)). Molecular dynamic studies suggest that the tricyclic core of the compounds is bound in a similar mode into the binding pocket, as described for doxepine in the hH1R crystal structure. Moreover, docking studies of all oxepine derivatives at the hH1R indicate that the oxygen and the position of the chlorine in the tricyclic core determines, if the R- or the S-enantiomer is the eutomer. For some of the oxazepines and oxepines the affinity to other aminergic GPCRs is in the same range as to hH1R or hH4R, thus, those compounds have to be classified as dirty drugs. However, one oxazepine derivative (3,7-Dichloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepine was identified as dual hH1/h5-HT2A receptor ligand (pKi: 9.23 (hH1R), 8.74 (h5-HT2AR), ≤7 at other analysed GPCRs), whereas one oxepine derivative (1-(3,8-Dichloro-6,11-dihydrodibenzo[b,e]oxepin-11-yl)-4-methylpiperazine) was identified as selective hH1R antagonist (pKi: 8.44 (hH1R), ≤6.7 at other analyzed GPCRs). Thus, the pharmacological results suggest that the oxazepine/oxepine moiety and additionally the chlorine substitution pattern toggles receptor selectivity and specificity.

Synthesis and evaluation of antipsychotic activity of 11-(4-aryl-1- piperazinyl)-dibenz [b, f][1,4] oxazepines and their 8-chloro analogues

Atypical drugs reduce positive and negative symptoms of schizophrenia, without inducing EPS, but they exert other undesirable side effects. We have gone for synthesis of novel derivatives of Loxapine which are devoid of catalepsy and have decreased metabolic demethylation which is the prominent factor for bioavailability of the drug. While doing so we have also been successful in retaining the antipsychotic activity of the drug. Condensation of 8,11-dichlorodibenzoxazepine and 11-chlorodibenzoxazepine with 1-aryl piperazines was carried to give 8-chloro-11-(4-aryl-1-piperazinyl)-dibenz[b,f] [1,4]oxazepines and 11-(4-aryl-1-piperazinyl)-dibenz[b,f][1,4]oxazepines respectively. These derivatives were found as active as Clozapine.

Loxapine analogs and methods of use thereof

The invention relates to novel compounds and methods of using them for modulating sleep.