Dibenz b f 1 4 oxazepine pdf

Regulatory process names 1 other names 1 other identifiers 1. Toxicological evaluation of 1chloroacetophenone and. The preparation of 2chloro11 1 piperazinyl dibenz b, f 1, 4 oxazepine by heating ethyl 4 opchlorophenoxyphenylcarbamoyl 1 piperazinecarboxylate with phosphorus pentoxide and phosphorus oxychloride, is described. The compound is a peripheral sensory irritant which produces an immediate irritation of the eyes, nose, mouth, skin, and respiratory tract in man. All the compounds mj1mj12 were synthesized by economical route and con. Barium 14 ccarbonate was purchased from amersham pharmacia biotech uk limited amersham. Dibenz b, f 1, 4 oxazepine 1 reacts with sodium dichloroisocyanurate ficlor under homogeneous conditions in aqueous ethanol to afford salicylaldehyde as the preponderant primary product, together with smaller amounts of nformylphenoxazine and 22hydroxyphenylbenzoxazole. Pdf molecular modeling studies on 11hdibenzb,eazepine. The comfa and comsia models resulting from a 21 molecule training set gave r2cv values of 0. Improved etherification procedure for the preparation of. Authority us united states prior art keywords piperazinyl ml dibenz example oxazepine prior art date 19680216 legal status the legal. R 3 is a hydrogen atom, a carboxyl group, a carbamoyl group, a lower alkoxycarbonyl group, or a lower alkoxy group.

R 4 and r 5 are each a lower alkyl group or may, when taken together with a nitrogen atom, form a heterocyclic ring. This has led to the discovery that most of the known tear gases are potent trpa1 activators. Upshall chemical defence establishment, porton down, wiltshire, u. Two distinct alternative methods using different starting materials for the preparation of dibenz b, f 1, 4 oxazepine 7, cr were reinvestigated. An efficient protocol for the catalytic asymmetric synthesis of new dibenzo b, f 1, 4 oxazepine fused 1,2dihydropyridines dhps has been described under metalfree conditions.

Analysis of the 1h and c1h nmr spectral parameters of. Mass spectrum electron ionization gas chromatography. Us4379150a us06331,897 us33189781a us4379150a us 4379150 a us4379150 a us 4379150a us 33189781 a us33189781 a us 33189781a us 4379150 a us4379150 a us 4379150a authority us unite. Dibenz b, f 1, 4 oxazepine, also known as cr gas and dibenzoxazepine, is an incapacitating agent and a lachrymatory agent. As a thirdgeneration tear agent, dibenz b, f 1, 4 oxazepine cr has been widely used for antiterrorism and riot control efforts. Sc51089 is a selective antagonist of prostaglandin e2, which displays specificity towards the ep1 receptor subtype.

It was developed by the british ministry of defence as a riot control agent in the late 1950s and early 1960s. Molecular modeling studies on 11h dibenz b,eazepine and dibenz b, f 1, 4 oxazepine derivatives as potent agonists of the human trpa1 receptor article pdf available in molecules 1512. Reinvestigation of alternative method for the preparation. The comfa and comsia models resulting from a 21 molecule training set gave r2 cv values of 0. Toxicological evaluation of 1 chloroacetophenone and dibenz b, f 1, 4 oxazepine after repeated inhalation exposure in mice. Onepot synthesis of chiral tetracyclic dibenzob,f1,4. Occupational exposure and exposure to the general population to dibenz b, f 1, 4 oxazepine should be rare since this compound is solely used as a riot control agent. The base compound and nontoxic acid addition salts are useful for their desirable effect on the central nervous system of warmblooded animals. Use this link for bookmarking this species for future reference. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.

Synthesis and evaluation of antipsychotic activity of 11. Ep0054951a1 dibenz b, f 1, 4 oxazepine derivatives. A repeated dose study of the toxicity of technical grade dibenz b. The trpa1 channel can be considered as a key biological sensor to irritant chemicals. All the products result from oxidation of the azomethine group in 1. A sequence of the ugi fourcomponent reaction u4cr and microwaveassisted intramolecular ullmann etherification has been established for efficient generation of a dibenz b, f 1, 4 oxazepine scaffold. The exchange of the nh group in clozapine by an oxygen resulted in the dibenzo b, f 1, 4 oxazepine derivatives, e. Reinvestigation of alternative method for the preparation of dibenz bf 1, 4 oxazepine article in journal of heterocyclic chemistry 465. When the rabbits were sacrificed and their eyes examined by light and electron microscopy, all structures of the cornea and palpebral conjunctiva were found to be normal.

Pdf toxicological evaluation of 1chloroacetophenone and. The 1h and c1h nmr spectra of the tear gases chloroacetophenone, dibenz b, f 1, 4 oxazepine and 2. To improve the efficiency of cr use and determine the toxicity of its decomposition products, it is necessary to study its thermal. Dibenz b, f 1, 4 oxazepine cr, a potent peripheral sensory irritant material, has been shown to have a very low acute lethal and sublethal toxicity by intravenous, intraperitoneal, oral, percutaneous and inhalation routes to several species of laboratory mammal.

Toxicological evaluation was made on the effects of two peripheral sensory irritants tear gases. Compounds mj 1, mj3 and mj 4 were found to be potent antipsychotic compounds of the series at 5mgkg dose level when compared with the reference drug clozapine. Preparation of substituted dibenz b, f 1, 4 oxazepine 1110hones from 2, 4,6trinitrobenzoic acid via nucleophilic displacement of nitro groups. Kumar p 1, flora sj, pant sc, sachan as, saxena sp, gupta sd. The irritant compound dibenz b, f 1, 4 oxazepine cr is a potential riot control agent because of its rapid but transient effects on the eyes and the respiratory tract. Trifluoromethylthio substituted dibenz b, f 1, 4 oxazepines download pdf info. With the aim to identify a new antagonisticinverse agonistic h 1 h 4 receptor scaffold beside the quinazoline scaffold, we focused on tricyclic compounds.

The effects of dibenzb,f1,4oxazepine cr upon rat and. Studies on thermal degradation of riot control agent. Studies on the uptake and metabolism of dibenzb,f1,4. Studies indicate that sc51089 can induce nociceptive behaviors in rats as a result of its antagonistic effects on prostaglandin e2. Synthetic utilization of polynitroaromatic compounds. This reaction proceeds through prolinecatalyzed direct mannichcyclization between sevenmembered dibenzo b, f 1, 4 oxazepine imines and aqueous glutaraldehyde, followed by ibxmediated siteselective dehydrogenative. The information in cameo chemicals comes from a variety of data sources.

Access to functionalized dibenzo b, f 1, 4 oxazepine derivatives hao deng department of applied chemistry, china agricultural university, 2 yuanmingyuan west road, beijing, 100193 peoples republic of china. Rucatalyzed asymmetric transfer hydrogenation of substituted dibenzo b, f 1, 4 oxazepines in waterganesh v. Dibenz b, f 1, 4 oxazepine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions. These rcas are characterized by rapid onset of effects and after the victim has been decontaminated andor escapes from the contaminated atmosphere the effects last for a brief period 1530 min another essential characteristic of the rcas is high margin of safe use. Analogues of morphanthridine and the tear gas dibenzb,f.

Hyphenated techniques of thermal analysis for dibenzb,f. Toxicology and applied pharmacology 29, 3011 1974 the effects of dibenz b, f 1, 4 oxazepine cr upon rat and rabbit embryonic development d. Clozapine 1 is a so called dirty drug, because it shows affinity to several gpcrs. The present study demonstrates significant antipsychotic activity for most of the compounds from series. Pdf a repeated dose study of the toxicity of technical.

Cr was developed by the british ministry of defence as a riot control agent in the late 1950s and early 1960s. This observation is in contrast with earlier results for the nitrosubstituted. The acute mammalian toxicology of dibenzb,f1,4oxazepine. The hazard fields include special hazard alerts air and water reactions, fire hazards, health hazards, a reactivity profile, and details about reactive groups assignments and potentially incompatible absorbents. Preparation of substituted dibenz b, f 1, 4 oxazepine 1110hones from 2, 4,6trinitrobenzoic acid via nucleophilic displacement of. Cr gas or dibenzoxazepine also referred to as dbo, or its chemical name dibenz b, f 1, 4 oxazepine, is an incapacitating agent and a lachrymatory agent. In this paper, the discovery of 11h dibenz b,eazepines morphanthridines and dibenz b, f 1, 4 oxazepines is described as extremely potent agonists of the trpa1 receptor. To improve the efficiency of cr use and determine the toxicity of. Hyphenated techniques of thermal analysis for dibenz b, f. A new synthetic route has been developed for the synthesis of seven membered heterocyclic ring dibenz b, f 1, 4 oxazepine cr starting with condensation of oaminophenol and ochlorobenzaldehyde. The aquatic toxicity of the sensory irritant and riot. A computational strategy based on comparative molecular fields analysis comfa and comparative molecular similarity indices analysis comsia was performed on a series of the 11h dibenz b,eazepine and dibenz b, f 1, 4 oxazepine derivatives as potent agonists of the human trpa1 receptor.