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N-Demethyldiazepam (FDB007124)

Record Information
Version1.0
Creation date2010-04-08 22:07:27 UTC
Update date2019-11-26 03:01:30 UTC
Primary IDFDB007124
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Demethyldiazepam
DescriptionN-demethyldiazepam, also known as nordiazepam or calmday, is a member of the class of compounds known as 1,4-benzodiazepines. 1,4-benzodiazepines are organic compounds containing a benzene ring fused to a 1,4-azepine. N-demethyldiazepam is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). N-demethyldiazepam can be found in common wheat, corn, and potato, which makes N-demethyldiazepam a potential biomarker for the consumption of these food products. N-demethyldiazepam can be found primarily in blood and urine, as well as in human kidney and liver tissues. N-demethyldiazepam is a non-carcinogenic (not listed by IARC) potentially toxic compound. General 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 (T3DB).
CAS Number1088-11-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
Chemical FormulaC15H11ClN2O
IUPAC name7-chloro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
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
Isomeric SMILESClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1
Average Molecular Weight270.714
Monoisotopic Molecular Weight270.055990691
Classification
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

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point216.5 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP2.93HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-006x-1290000000-16289dee622e983dadb42014-10-20View Spectrum
Predicted GC-MSN-Demethyldiazepam, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06tf-0190000000-29b106f0dfb9b4601898Spectrum
Predicted GC-MSN-Demethyldiazepam, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0090000000-08ab493d917dff5568032017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0090000000-b3902adae33dd2ada9962017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0090000000-e1f36555cb45aafb35782017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0090000000-4599707b6c514e2fd1402017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0090000000-2afa9f8bad136457e9132017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-052f-0090000000-39292916fbbd987c9c792017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0490000000-93d06070b3ddb4f2bb1d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0900000000-319db7de66dd214c60362017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-f12d8a37190a6a1a62602017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dl-0590000000-6667f22f2eaaa4d7d4442017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05mo-0950000000-9f91849bf0ea300eddf62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-052f-0940000000-113f94a665f60922a3cc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0090000000-a17b063554f54d5ae7902017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0090000000-00d132ae0ea246d26e2a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0390000000-02873020d1329d3d5c382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-1960000000-010c3ba06f80d4ace9942017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052f-1930000000-327cc931b60592065b642017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-2910000000-0a0897ca546d1bc1cb272017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f6x-4900000000-7cc6b852b0d715a021c22017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-42b4ac66c7efbf805ab72016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-eade00da0853b4fc330e2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9760000000-acfef25bde706bde8e9d2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-1ed0d3938bd2d416daef2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-63aef3ca2706dc88c39f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9220000000-e0ad5d0ad9c04e3b5ca92016-08-03View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC07486
Pubchem Compound ID2997
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDN-DEMETHYL-DIAZEPAM
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anxiolytic35474 Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.CHEBI
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).