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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:09:24 UTC
Update Date2021-09-14 15:45:14 UTC
HMDB IDHMDB0060956
Secondary Accession Numbers
  • HMDB60956
Metabolite Identification
Common NameN-desmethylmirtazapine
DescriptionN-desmethylmirtazapine is a metabolite of mirtazapine. Mirtazapine (Remeron, Avanza, Zispin) is a noradrenergic and specific serotonergic antidepressant (NaSSA) which was introduced by Organon International in the United States in 1990 and is used primarily in the treatment of depression. It is also commonly used as an anxiolytic, hypnotic, antiemetic, and appetite stimulant. Structurally, mirtazapine can also be classified as a tetracyclic antidepressant (TeCA). (Wikipedia)
Structure
Data?1563866128
Synonyms
ValueSource
DesmethylmirtazapineMeSH
DemethylmirtazapineMeSH
Chemical FormulaC16H17N3
Average Molecular Weight251.3263
Monoisotopic Molecular Weight251.142247559
IUPAC Name2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaene
Traditional Name2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaene
CAS Registry NumberNot Available
SMILES
C1CN2C(CN1)C1=CC=CC=C1CC1=C2N=CC=C1
InChI Identifier
InChI=1S/C16H17N3/c1-2-6-14-12(4-1)10-13-5-3-7-18-16(13)19-9-8-17-11-15(14)19/h1-7,15,17H,8-11H2
InChI KeyFGLAMNFOHWVQOH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as piperazinoazepines. Piperazinoazepines are compounds containing a piperazinoazepine skeleton, which consists of an azepine ring fused to a piperazine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperazinoazepines
Sub ClassNot Available
Direct ParentPiperazinoazepines
Alternative Parents
Substituents
  • Benzazepine
  • Piperazino-azepine
  • Dialkylarylamine
  • Azepine
  • Aralkylamine
  • 1,4-diazinane
  • Piperazine
  • Imidolactam
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP2.13ALOGPS
logP2.82ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)8.75ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.16 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity77.36 m³·mol⁻¹ChemAxon
Polarizability27.97 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+155.73331661259
DarkChem[M-H]-154.85831661259
DeepCCS[M+H]+159.26630932474
DeepCCS[M-H]-156.90930932474
DeepCCS[M-2H]-189.79530932474
DeepCCS[M+Na]+165.3630932474
AllCCS[M+H]+159.432859911
AllCCS[M+H-H2O]+155.432859911
AllCCS[M+NH4]+163.032859911
AllCCS[M+Na]+164.132859911
AllCCS[M-H]-166.432859911
AllCCS[M+Na-2H]-165.832859911
AllCCS[M+HCOO]-165.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-desmethylmirtazapineC1CN2C(CN1)C1=CC=CC=C1CC1=C2N=CC=C13459.4Standard polar33892256
N-desmethylmirtazapineC1CN2C(CN1)C1=CC=CC=C1CC1=C2N=CC=C12239.1Standard non polar33892256
N-desmethylmirtazapineC1CN2C(CN1)C1=CC=CC=C1CC1=C2N=CC=C12378.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-desmethylmirtazapine,1TMS,isomer #1C[Si](C)(C)N1CCN2C3=NC=CC=C3CC3=CC=CC=C3C2C12470.1Semi standard non polar33892256
N-desmethylmirtazapine,1TMS,isomer #1C[Si](C)(C)N1CCN2C3=NC=CC=C3CC3=CC=CC=C3C2C12515.6Standard non polar33892256
N-desmethylmirtazapine,1TMS,isomer #1C[Si](C)(C)N1CCN2C3=NC=CC=C3CC3=CC=CC=C3C2C13164.9Standard polar33892256
N-desmethylmirtazapine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN2C3=NC=CC=C3CC3=CC=CC=C3C2C12685.2Semi standard non polar33892256
N-desmethylmirtazapine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN2C3=NC=CC=C3CC3=CC=CC=C3C2C12746.1Standard non polar33892256
N-desmethylmirtazapine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN2C3=NC=CC=C3CC3=CC=CC=C3C2C13346.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-desmethylmirtazapine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0390000000-9f5ecf4547494620e4cb2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-desmethylmirtazapine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylmirtazapine 10V, Positive-QTOFsplash10-0udi-0090000000-964bb70179075fb2b3642017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylmirtazapine 20V, Positive-QTOFsplash10-0udi-0090000000-640b11e80d6d5473fa222017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylmirtazapine 40V, Positive-QTOFsplash10-0a4i-9850000000-24e8e860e77ddc872ac52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylmirtazapine 10V, Negative-QTOFsplash10-0udi-0090000000-fbf43ffa32573f90abc22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylmirtazapine 20V, Negative-QTOFsplash10-0udi-0090000000-c1d9598e4cb619a891df2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylmirtazapine 40V, Negative-QTOFsplash10-0006-3920000000-5144479e97e40b1080822017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylmirtazapine 10V, Negative-QTOFsplash10-0udi-0090000000-32785a3fe19ac75a632b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylmirtazapine 20V, Negative-QTOFsplash10-0udi-0090000000-32785a3fe19ac75a632b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylmirtazapine 40V, Negative-QTOFsplash10-006x-1960000000-0e42ea918e27feb075b92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylmirtazapine 10V, Positive-QTOFsplash10-0udi-0090000000-a5f76b53c23417fe17292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylmirtazapine 20V, Positive-QTOFsplash10-0udi-0090000000-a5f76b53c23417fe17292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-desmethylmirtazapine 40V, Positive-QTOFsplash10-0a4j-1490000000-bb9c59307aedfa1b68a32021-09-24Wishart 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
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10467350
PDB IDNot Available
ChEBI IDNot Available
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