Dibenz(b,F)-1,4-oxazepine (T3D4658)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-09-08 02:41:29 UTC
Update Date2014-12-24 20:26:54 UTC
Accession NumberT3D4658
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.
Compound Type
  • Ether
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Dibenzo[b,F][1,4]Oxazepine
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
SMILESO1C2=CC=CC=C2C=NC2=CC=CC=C12
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 KeyInChIKey=NPUACKRELIJTFM-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
LogPNot 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 RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-0900000000-f32410c76b2c66da00962021-09-23View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-574736603d41da76ac7e2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0d54063e0b78113d6f202016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9000000000-f1043bb6e710e8f8aec12016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-b5ac83732cc40dd778a02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-c25fd4ff43540c7aff732016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0900000000-20f9b8c4e33802c0619b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-0310cae5b7a4706b20382021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0310cae5b7a4706b20382021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900000000-b394949869914211006c2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-fe1bdc84baadae0a8c3d2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-fe1bdc84baadae0a8c3d2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-0900000000-c42ddd885d7c716b0a8f2021-10-12View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID9213
ChEMBL IDCHEMBL1085100
ChemSpider ID8858
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkCR_gas
References
Synthesis ReferenceNot Available
MSDST3D4658.pdf
General References
  1. Brone B, Peeters PJ, Marrannes R, Mercken M, Nuydens R, Meert T, Gijsen HJ: Tear gasses CN, CR, and CS are potent activators of the human TRPA1 receptor. Toxicol Appl Pharmacol. 2008 Sep 1;231(2):150-6. doi: 10.1016/j.taap.2008.04.005. Epub 2008 Apr 20. [18501939 ]
  2. Gijsen HJ, Berthelot D, Zaja M, Brone B, Geuens I, Mercken M: Analogues of morphanthridine and the tear gas dibenz[b,f][1,4]oxazepine (CR) as extremely potent activators of the human transient receptor potential ankyrin 1 (TRPA1) channel. J Med Chem. 2010 Oct 14;53(19):7011-20. doi: 10.1021/jm100477n. [20806939 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]