You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:23:18 UTC
Update Date2017-10-23 19:15:43 UTC
HMDB IDHMDB0060472
Secondary Accession Numbers
  • HMDB60472
Metabolite Identification
Common NameDidemethylcitalopram
DescriptionIn humans, CITA is metabolized to demethylcitalopram (DCITA) by CYP2C19, CYP2D6, and CYP3A and to didemethylcitalopram by CYP2D6. (PMID: 19011672 ) The major metabolite of citalopram is demethylcitalopram, which is subsequently metabolized to the minor metabolite didemethylcitalopram (DDCT). (PMID: 22085614 )
Structure
Thumb
Synonyms
ValueSource
Didesmethylcitalopram oxalateMeSH
Chemical FormulaC18H17FN2O
Average Molecular Weight296.3388
Monoisotopic Molecular Weight296.132491381
IUPAC Name1-(3-aminopropyl)-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
Traditional Namedidemethylcitalopram
CAS Registry NumberNot Available
SMILES
NCCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
InChI Identifier
InChI=1S/C18H17FN2O/c19-16-5-3-15(4-6-16)18(8-1-9-20)17-7-2-13(11-21)10-14(17)12-22-18/h2-7,10H,1,8-9,12,20H2
InChI KeyRKUKMUWCRLRPEJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylbutylamines
Alternative Parents
Substituents
  • Phenylbutylamine
  • Isocoumaran
  • Fluorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl halide
  • Aryl fluoride
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Carbonitrile
  • Nitrile
  • Organoheterocyclic compound
  • Organohalogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Amine
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0053 g/LALOGPS
logP2.69ALOGPS
logP2.95ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)10.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.04 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity83.95 m³·mol⁻¹ChemAxon
Polarizability31.16 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-5190000000-27267b21fbfd2667ad0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0090000000-6d8ae8086154e9386c59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1190000000-a3bd6197e10242280d3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9850000000-29310282b6b9fbd8e49fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-b966c93238a3cd3d8dbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1090000000-6f09b8194f9dc7f22ae0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-5290000000-4ebf655263c971b6b6fcView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Citalopram Metabolism PathwayPw000603Pw000603 greyscalePw000603 simpleNot Available
Citalopram PathwayPw000426Pw000426 greyscalePw000426 simpleNot Available
Displaying all 2 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00661
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16609
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound0
      PDB IDNot Available
      ChEBI ID80604
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
      2. Howland RH: A critical evaluation of the cardiac toxicity of citalopram: part 2. J Psychosoc Nurs Ment Health Serv. 2011 Dec;49(12):13-6. doi: 10.3928/02793695-20111102-04. Epub 2011 Nov 16. [PubMed:22085614 ]
      3. Rocha A, Coelho EB, Lanchote VL: Influence of quinidine, fluvoxamine, and ketoconazole on the enantioselective pharmacokinetics of citalopram in rats. Can J Physiol Pharmacol. 2008 Nov;86(11):770-6. doi: 10.1139/Y08-088. [PubMed:19011672 ]

      Enzymes

      General function:
      Involved in oxidoreductase activity
      Specific function:
      Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
      Gene Name:
      MAOB
      Uniprot ID:
      P27338
      Molecular weight:
      58762.475
      Reactions
      Didemethylcitalopram + Water + Oxygen → Citalopram aldehyde + Ammonia + Hydrogen peroxidedetails
      General function:
      Involved in oxidoreductase activity
      Specific function:
      Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
      Gene Name:
      MAOA
      Uniprot ID:
      P21397
      Molecular weight:
      59681.27
      Reactions
      Didemethylcitalopram + Water + Oxygen → Citalopram aldehyde + Ammonia + Hydrogen peroxidedetails