Nordiazepam (CHEM003548)

Record Information
Version1.0
Creation Date2014-09-05 17:11:30 UTC
Update Date2026-05-14 19:39:34 UTC
Accession NumberCHEM003548
Identification
Common NameNordiazepam
ClassSmall Molecule
Description
Nordiazepam 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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
External Links
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