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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:47:58 UTC
Update Date2021-09-14 14:58:20 UTC
HMDB IDHMDB0041919
Secondary Accession Numbers
  • HMDB41919
Metabolite Identification
Common NameLormetazepam
DescriptionLormetazepam (INN, or methyl-lorazepam, is a drug which is a short to intermediate acting 3-hydroxy benzodiazepine derivative. It possesses hypnotic, anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Lormetazepam is considered a hypnotic benzodiazepine and is officially indicated for moderate to severe insomnia. Lormetazepam is a short-acting benzodiazepine and is sometimes used in patients who have difficulty in maintaining sleep or falling asleep. Hypnotics should only be used on a short-term basis or, in those with chronic insomnia, on an occasional basis.
Structure
Data?1563863714
Synonyms
ValueSource
(+-)-LorazepamChEBI
7-Chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-oneChEBI
7-Chloro-5-(O-chlorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-2H-1,4-benzodiazepin-2-oneChEBI
LorametChEBI
LorazepamChEBI
LormetazepamumChEBI
MethyllorazepamChEBI
N-MethyllorazepamChEBI
O-ChlorooxazepamChEBI
O-ChloroxazepamChEBI
()-LorazepamHMDB
7-chloro-5-(2-Chlorophenyl)-3-hydroxy-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-oneHMDB
ErgocalmHMDB
NoctamidHMDB
NoctamideHMDB
Chemical FormulaC16H12Cl2N2O2
Average Molecular Weight335.185
Monoisotopic Molecular Weight334.027583052
IUPAC Name7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
Traditional Namelormetazepam
CAS Registry Number848-75-9
SMILES
CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1Cl
InChI Identifier
InChI=1S/C16H12Cl2N2O2/c1-20-13-7-6-9(17)8-11(13)14(19-15(21)16(20)22)10-4-2-3-5-12(10)18/h2-8,15,21H,1H3
InChI KeyFJIKWRGCXUCUIG-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
  • Alpha-amino acid or derivatives
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Ketimine
  • Lactam
  • Alkanolamine
  • Carboxylic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Imine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point206 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM169.530932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP10(2.92) g/LALOGPS
logP10(3.39) g/LChemAxon
logS10(-4.3) g/LALOGPS
pKa (Strongest Acidic)10.68ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.9 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity85.82 m³·mol⁻¹ChemAxon
Polarizability32.21 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LormetazepamCN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1Cl4101.8Standard polar33892256
LormetazepamCN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1Cl2660.5Standard non polar33892256
LormetazepamCN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C1=CC=CC=C1Cl2710.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lormetazepam,1TMS,isomer #1CN1C(=O)C(O[Si](C)(C)C)N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C212757.2Semi standard non polar33892256
Lormetazepam,1TBDMS,isomer #1CN1C(=O)C(O[Si](C)(C)C(C)(C)C)N=C(C2=CC=CC=C2Cl)C2=CC(Cl)=CC=C212899.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Lormetazepam EI-B (Non-derivatized)splash10-0a4i-1219000000-503deaa645713d28cd792017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Lormetazepam EI-B (Non-derivatized)splash10-0a4i-1219000000-503deaa645713d28cd792018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lormetazepam GC-MS (Non-derivatized) - 70eV, Positivesplash10-00or-1795000000-54ec577d366419e67a572017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lormetazepam GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9327000000-b97471e8ca7fa14dc66e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lormetazepam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lormetazepam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-2739000000-db8dc59f3b0cd2b1f9612014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lormetazepam 10V, Positive-QTOFsplash10-000i-0029000000-b740d9673443070572762016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lormetazepam 20V, Positive-QTOFsplash10-000i-0229000000-85f6cd437be8449454542016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lormetazepam 40V, Positive-QTOFsplash10-000l-1930000000-5956d587779e5dd037d02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lormetazepam 10V, Negative-QTOFsplash10-001i-0009000000-f8c21520624f2329615b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lormetazepam 20V, Negative-QTOFsplash10-0059-0395000000-294d5b2fafa29dcbd1ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lormetazepam 40V, Negative-QTOFsplash10-0bvi-5592000000-60b8f74cbf9e0379ec5c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lormetazepam 10V, Positive-QTOFsplash10-000i-0029000000-5de67bfbe23ce4a7f6ba2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lormetazepam 20V, Positive-QTOFsplash10-002r-0069000000-a5d15166483d3298eae02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lormetazepam 40V, Positive-QTOFsplash10-03fr-0290000000-81ca3eb9e5b8757a95752021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lormetazepam 10V, Negative-QTOFsplash10-001j-0079000000-7a1a623dc11cf39fac8e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lormetazepam 20V, Negative-QTOFsplash10-001j-3096000000-66c851b8c2851ab6f2f72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lormetazepam 40V, Negative-QTOFsplash10-001i-9141000000-2888eb8630631357a90b2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 IDDB13872
Phenol Explorer Compound IDNot Available
FooDB IDFDB007119
KNApSAcK IDNot Available
Chemspider ID12750
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLormetazepam
METLIN IDNot Available
PubChem Compound13314
PDB IDNot Available
ChEBI ID52993
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available