Dibenz(b,F)-1,4-oxazepine (CHEM003616)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2014-09-08 02:41:29 UTC
Update Date2026-04-03 19:32:46 UTC
Accession NumberCHEM003616
Identification
Common NameDibenz(b,F)-1,4-oxazepine
ClassSmall Molecule
DescriptionDibenz(b,F)-1,4-oxazepine, also known as CR gas and dibenzoxazepine, is an incapacitating agent and a lachrymatory agent. It was developed by the British Ministry of Defence as a riot control agent in the late 1950s and early 1960s. Dibenz(b,F)-1,4-oxazepine is a lachrymatory agent (LA), exerting its effects through activation of the TRPA1 channel. It is a suspected carcinogen. It is toxic, but less so than CS gas (2-chlorobenzalmalononitrile), by ingestion and exposure. However, it can be lethal in large quantities. In a poorly ventilated space, an individual may inhale a lethal dose within minutes. Death is caused by asphyxiation and pulmonary edema. The effect of CR is long-term and persistent. CR can persist on surfaces, especially porous ones, for up to 60 days.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Ether
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
dibenzo[BF][14]OxazepineChEMBL
Dibenz[BF][14]oxazepineChEMBL
CR IrritantMeSH
Dibenz(b,F)(1,4)oxazepineMeSH
Chemical FormulaC13H9NO
Average Molecular Mass195.217 g/mol
Monoisotopic Mass195.068 g/mol
CAS Registry Number257-07-8
IUPAC Name2-oxa-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene
Traditional Namedibenz(b,f)(1,4)oxazepine
SMILES[H]C1=C([H])C([H])=C2N=C([H])C3=C([H])C([H])=C([H])C([H])=C3OC2=C1[H]
InChI IdentifierInChI=1S/C13H9NO/c1-3-7-12-10(5-1)9-14-11-6-2-4-8-13(11)15-12/h1-9H
InChI KeyNPUACKRELIJTFM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzoxazepines. Dibenzoxazepines are compounds containing a dibenzoxazepine moiety, which consists of two benzene connected by an oxazepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazepines
Sub ClassDibenzoxazepines
Direct ParentDibenzoxazepines
Alternative Parents
Substituents
  • Dibenzoxazepine
  • Diaryl ether
  • Benzenoid
  • Ether
  • Oxacycle
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
  • Microsome
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearancePale yellow crystalline solid
Experimental Properties
PropertyValue
Melting Point73°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0086 g/LALOGPS
logP3.13ALOGPS
logP3.37ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)0.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area21.59 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity61.57 m³·mol⁻¹ChemAxon
Polarizability20.58 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-0900000000-f32410c76b2c66da0096Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-574736603d41da76ac7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0d54063e0b78113d6f20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9000000000-f1043bb6e710e8f8aec1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-b5ac83732cc40dd778a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-c25fd4ff43540c7aff73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0900000000-20f9b8c4e33802c0619bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-0310cae5b7a4706b2038Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0310cae5b7a4706b2038Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900000000-b394949869914211006cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-fe1bdc84baadae0a8c3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-fe1bdc84baadae0a8c3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-0900000000-c42ddd885d7c716b0a8fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0245702
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8858
ChEBI IDNot Available
PubChem Compound ID9213
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available