267220-45-1

Basic information

• Product Name: 2-Oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxamide(9CI)
• Synonyms: 2-Oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxamide(9CI)
• CAS NO: 267220-45-1
• Molecular Formula: C7H10N2O2
• Molecular Weight: 154.17
• Product Categories: AMIDE
• Mol File: 267220-45-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 252.6±43.0 °C(Predicted)
• Appearance: /
• Density: 1.320±0.06 g/cm3(Predicted)
• PKA: 14.87±0.20(Predicted)
• CAS DataBase Reference: 2-Oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxamide(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxamide(9CI)(267220-45-1)
• EPA Substance Registry System: 2-Oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxamide(9CI)(267220-45-1)

Safety Data

• Hazardous Substances Data: 267220-45-1(Hazardous Substances Data)

Upstream product

• 1165952-91-9 cyclohexa-1,3-diene 
• 104308-46-5 9,10-(N-carbamoylepoxyimino)-9,10-dihydro-9,10-dimethylanthracene 
• 127-07-1 N-hydroxyurea 

Relevant articles and documents

Catalase-mediated nitric oxide formation from hydroxyurea

Hydroxyurea reduces the incidence of painful crises in patients with sickle cell disease and has recently been approved for the treatment of this condition. A number of in vitro studies show that the oxidation of hydroxyurea results in the formation of nitric oxide, which also has drawn considerable interest as a sickle cell disease therapy. While patients on hydroxyurea demonstrate elevated levels of nitric oxide-derived metabolites, little information regarding the site or mechanism of the in vivo conversion of hydroxyurea to nitric oxide exists. Chemiluminescence detection experiments show the ability of catalase to catalyze the formation of nitrite and nitrate from hydroxyurea. Spectroscopic studies show that the reaction of hydroxyurea and catalase in the presence of a hydrogen peroxide generating system produces a ferrous-NO catalase complex. Trapping studies indicate the intermediacy of a nitroso species during this reaction. The proposed mechanism for this conversion includes initial hydrogen peroxide-dependent oxidation of hydroxyurea by catalase to form the nitroso species, hydrolysis of this nitroso species to produce nitroxyl, and reductive nitrosylation of the ferric heme of catalase by nitroxyl to yield the ferrous-NO catalase complex. Addition of Angeli's salt, a nitroxyl donor, to ferric catalase also produces the ferrous-NO catalase complex. Spectroscopic studies show that the ferrous-NO catalase complex releases nitric oxide as judged by the oxyhemoglobin assay and an NO specific EPR specific trap. These results demonstrate nitric oxide production from the ferric catalase oxidation of nitroxyl and identify a catalase-mediated pathway as a potential source of nitric oxide production from hydroxyurea.

Production of nitroxyl (HNO) at biologically relevant temperatures from the retro-Diels-Alder reaction of N-hydroxyurea-derived acyl nitroso-9,10- dimethylanthracene cycloadducts

Retro Diels-Alder reaction of N-hydroxyurea-derived acyl nitroso compound-9,10-dimethylanthracene cycloadducts produce acyl nitroso compounds that react with nucleophiles to form nitrous oxide, which indicates the intermediacy of nitroxyl. These results identify these molecules as a new group of nitroxyl delivery agents. (C) 2000 Elsevier Science Ltd.

Generation of acyl nitroso compounds by the oxidation of N-acyl hydroxylamines with the Dess-Martin periodinane

The oxidation of hydroxamic acids, N-hydroxyureas and N- hydroxycarbamates with the Dess-Martin periodinane generates the corresponding acyl nitroso compounds that react with conjugated dienes to produce the corresponding cycloadducts.