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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-12 17:32:41 UTC
Update Date2019-07-23 07:14:33 UTC
HMDB IDHMDB0060538
Secondary Accession Numbers
  • HMDB0061094
  • HMDB60538
  • HMDB61094
Metabolite Identification
Common NameNordiazepam
DescriptionNordiazepam, also known as desmethyldiazepam or dealkylprazepam, 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. 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. Nordiazepam is a moderately basic compound (based on its pKa). Outside of the human body, Nordiazepam has been detected, but not quantified in, a few different foods, such as common wheats, corns, and potato. This could make nordiazepam a potential biomarker for the consumption of these foods. 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. Nordiazepam is a potentially toxic compound. 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. Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. General supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained.
Structure
Data?1563866073
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 Weight270.714
Monoisotopic Molecular Weight270.055990691
IUPAC Name7-chloro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
Traditional Namenordiazepam
CAS Registry Number1088-11-5
SMILES
ClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
logP10(2.79) g/LALOGPS
logP10(3.21) g/LChemAxon
logS10(-4.1) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nordiazepam GC-MS (Non-derivatized) - 70eV, Positivesplash10-06tf-0190000000-29b106f0dfb9b46018982017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nordiazepam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-006x-1290000000-16289dee622e983dadb42014-10-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOFsplash10-014i-0090000000-08ab493d917dff5568032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOFsplash10-0006-0090000000-b3902adae33dd2ada9962017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOFsplash10-0006-0090000000-e1f36555cb45aafb35782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOFsplash10-0006-0090000000-4599707b6c514e2fd1402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOFsplash10-0006-0090000000-2afa9f8bad136457e9132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOFsplash10-052f-0090000000-39292916fbbd987c9c792017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOFsplash10-0udi-0490000000-93d06070b3ddb4f2bb1d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , negative-QTOFsplash10-0udi-0900000000-319db7de66dd214c60362017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QTOF , positive-QTOFsplash10-00di-0090000000-f12d8a37190a6a1a62602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QTOF , positive-QTOFsplash10-00dl-0590000000-6667f22f2eaaa4d7d4442017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QTOF , positive-QTOFsplash10-05mo-0950000000-9f91849bf0ea300eddf62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QTOF , positive-QTOFsplash10-052f-0940000000-113f94a665f60922a3cc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOFsplash10-00di-0090000000-a17b063554f54d5ae7902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOFsplash10-00di-0090000000-00d132ae0ea246d26e2a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOFsplash10-00di-0390000000-02873020d1329d3d5c382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOFsplash10-0006-1960000000-010c3ba06f80d4ace9942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOFsplash10-052f-1930000000-327cc931b60592065b642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOFsplash10-0006-2910000000-0a0897ca546d1bc1cb272017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nordiazepam LC-ESI-QFT , positive-QTOFsplash10-0f6x-4900000000-7cc6b852b0d715a021c22017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordiazepam 10V, Positive-QTOFsplash10-00di-0090000000-42b4ac66c7efbf805ab72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordiazepam 20V, Positive-QTOFsplash10-00di-0090000000-eade00da0853b4fc330e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordiazepam 40V, Positive-QTOFsplash10-0k96-9760000000-acfef25bde706bde8e9d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordiazepam 10V, Negative-QTOFsplash10-014i-0090000000-1ed0d3938bd2d416daef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordiazepam 20V, Negative-QTOFsplash10-014i-0090000000-63aef3ca2706dc88c39f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordiazepam 40V, Negative-QTOFsplash10-0006-9220000000-e0ad5d0ad9c04e3b5ca92016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB007124
KNApSAcK IDNot Available
Chemspider ID2890
KEGG Compound IDC07486
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDesmethyldiazepam
METLIN IDNot Available
PubChem Compound2997
PDB IDNot Available
ChEBI ID111762
Food Biomarker OntologyNot Available
VMH IDC07486
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available