Nordiazepam (CHEM003548)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2014-09-05 17:11:30 UTC
Update Date2016-11-09 01:09:10 UTC
Accession NumberCHEM003548
Identification
Common NameNordiazepam
ClassSmall Molecule
DescriptionNordiazepam is a metabolite of Diazepam. Diazepam, first marketed as Valium by Hoffmann-La Roche, is a benzodiazepine drug. Nordazepam, also known as desoxydemoxepam, nordiazepam and desmethyldiazepam, is a 1,4-benzodiazepine derivative. Like other benzodiazepine derivatives, it has anticonvulsant, anxiolytic, muscle relaxant and sedative properties. (Wikipedia)
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • Suspected Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Drug
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-DemethyldiazepamChEBI
7-Chloro-1,3-dihydro-5-phenyl-(2H)-1,4-benzodiazepin-2-oneChEBI
7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-oneChEBI
7-Chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-oneChEBI
ChlordesmethyldiazepamChEBI
DealkylprazepamChEBI
DesmethyldiazepamChEBI
N-DemethyldiazepamChEBI
N-DeoxydemoxepamChEBI
N-DesmethyldiazepamChEBI
N1-DesmethyldiazepamChEBI
NordazepamumChEBI
NorprazepamChEBI
CalmdayKegg
NordiazepamChEBI
N-DescyclopropylmethylprazepamMeSH
Tranxilium NMeSH
VegesanMeSH
N Descyclopropylmethyl prazepamMeSH
N DesalkylhalazepamMeSH
N DestrifluoroethylhalazepamMeSH
N DescyclopropylmethylprazepamMeSH
NordazMeSH
NordazepamMeSH
DemethyldiazepamMeSH
N-Descyclopropylmethyl-prazepamMeSH
N-DestrifluoroethylhalazepamMeSH
DeoxydemoxepamMeSH
N-DesalkylhalazepamMeSH
Chemical FormulaC15H11ClN2O
Average Molecular Mass270.714 g/mol
Monoisotopic Mass270.056 g/mol
CAS Registry Number1088-11-5
IUPAC Name7-chloro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
Traditional Namenordiazepam
SMILESClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1
InChI IdentifierInChI=1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)
InChI KeyAKPLHCDWDRPJGD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,4-benzodiazepines
Alternative Parents
Substituents
  • 1,4-benzodiazepine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Cyclic carboximidic acid
  • Ketimine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
logP2.79ALOGPS
logP3.21ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.3ChemAxon
pKa (Strongest Basic)2.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.7 m³·mol⁻¹ChemAxon
Polarizability27.41 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06tf-0190000000-29b106f0dfb9b4601898Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0090000000-08ab493d917dff556803Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0090000000-b3902adae33dd2ada996Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0090000000-e1f36555cb45aafb3578Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0090000000-4599707b6c514e2fd140Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0090000000-2afa9f8bad136457e913Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-052f-0090000000-39292916fbbd987c9c79Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0490000000-93d06070b3ddb4f2bb1dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0900000000-319db7de66dd214c6036Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-f12d8a37190a6a1a6260Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dl-0590000000-6667f22f2eaaa4d7d444Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05mo-0950000000-9f91849bf0ea300eddf6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-052f-0940000000-113f94a665f60922a3ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0090000000-a17b063554f54d5ae790Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0090000000-00d132ae0ea246d26e2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0390000000-02873020d1329d3d5c38Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-1960000000-010c3ba06f80d4ace994Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052f-1930000000-327cc931b60592065b64Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-2910000000-0a0897ca546d1bc1cb27Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f6x-4900000000-7cc6b852b0d715a021c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-42b4ac66c7efbf805ab7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-eade00da0853b4fc330eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9760000000-acfef25bde706bde8e9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-1ed0d3938bd2d416daefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-63aef3ca2706dc88c39fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9220000000-e0ad5d0ad9c04e3b5ca9Spectrum
MSMass Spectrum (Electron Ionization)splash10-006x-1290000000-16289dee622e983dadb4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityBenzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentGeneral supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060538
FooDB IDFDB007124
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDesmethyldiazepam
Chemspider ID2890
ChEBI ID111762
PubChem Compound ID2997
Kegg Compound IDC07486
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16622
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19604
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=360230
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=364005
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=367407
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=4953859