Record Information
Version1.0
Creation date2011-09-21 00:32:18 UTC
Update date2015-10-09 22:33:06 UTC
Primary IDFDB023605
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCitalopram
DescriptionCitalopram is an antidepressant drug used to treat depression associated with mood disorders. It is also used on occasion in the treatment of body dysmorphic disorder and anxiety; Citalopram belongs to a class of drugs known as selective serotonin reuptake inhibitors (SSRIs). It is sold under the brand-names Celexa (U.S., Forest Laboratories, Inc.), Cipramil, Seropram (Europe and Australia) and Ciazil (Australia); A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from tardive dyskinesia in preference to tricyclic antidepressants, which aggravate this condition; Citalopram is an antidepressant drug used to treat depression associated with mood disorders. It is also used on occasion in the treatment of body dysmorphic disorder and anxiety. Citalopram belongs to a class of drugs known as selective serotonin reuptake inhibitors (SSRIs). [HMDB]
CAS Number59729-33-8
Structure
Thumb
Synonyms
SynonymSource
CitadurKegg
BonitrileHMDB
CelexaHMDB
Citalopram hydrobromideHMDB
NitalapramHMDB
EscitalopramHMDB
CytalopramHMDB
LexaproHMDB
Escitalopram oxalateHMDB
SeropramHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.0059 g/LALOGPS
logP3.58ALOGPS
logP3.76ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area36.26 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.02 m³·mol⁻¹ChemAxon
Polarizability35.3 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H21FN2O
IUPAC name1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
InChI IdentifierInChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3
InChI KeyWSEQXVZVJXJVFP-UHFFFAOYSA-N
Isomeric SMILESCN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
Average Molecular Weight324.3919
Monoisotopic Molecular Weight324.163791509
Classification
Description Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylbutylamines
Direct ParentPhenylbutylamines
Alternative Parents
Substituents
  • Phenylbutylamine
  • Isocoumaran
  • Fluorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl halide
  • Aryl fluoride
  • Tertiary amine
  • Tertiary aliphatic amine
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Carbonitrile
  • Nitrile
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Amine
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Role

Biological role:

Environmental role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
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)splash10-0a4i-9110000000-5b1fde1b7a58929c7f2d2014-09-20View Spectrum
Predicted GC-MSCitalopram, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-6190000000-9c092c583199a2a486efSpectrum
Predicted GC-MSCitalopram, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitalopram, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitalopram, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0009000000-589e7ae88aee7da0e0bd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0029000000-8fd40dc922da5ab2c8b02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0291000000-c60cbea4e4e6acbb45992017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00l2-0290000000-f2131534473e56b3c8a72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00mk-0390000000-e6cd61150feeca1d28672017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0291000000-ff658bd6b54adccbaf032017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0009000000-67fa40aabd862948aaf32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0129000000-60abdaff2f5d8f72e2712017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0bt9-0981000000-1eba423765a46f1dd6b92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0980000000-514f2e0bb73903b25b902017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0970000000-f27f46e3a573498d9f9b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0980000000-5ba355c707bc5008c0672017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0009000000-a115136f2084cc2a6a472017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0129000000-474ae50db9e74e5a31be2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0bt9-0981000000-011dbb85d8e7914863972017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0970000000-99aedc452f996b9c91132017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0980000000-c8734dde2a469350af7c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0970000000-cff11d70160f94e8fc2e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0391000000-e7862ea10a18e5771adc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0980000000-d24616414bd7fc5e11822017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0970000000-1c68a33d62afa46120712017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0394000000-f3c86fb3bf5bc76693072017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0390000000-5c227e85878c48f06a422017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0239000000-900cc91bba3c1f9f36742017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03di-0291000000-50d4588c6e576ed9479b2021-09-20View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID2669
ChEMBL IDCHEMBL549
KEGG Compound IDC07572
Pubchem Compound ID2771
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00215
HMDB IDHMDB05038
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
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 IDCitalopram
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference