Citalopram (CED0001619)

Record Information
Version1.0
Creation Date2009-07-21 20:26:18 UTC
Update Date2026-05-14 16:24:44 UTC
SynCED IDCED0001619
Secondary Accession Numbers
  • CHEM002145
  • T3D2715
Identification
Common NameCitalopram
ClassSmall Molecule
Description
Citalopram belongs to the phenylbutylamines, a subclass of benzene and substituted derivatives within the organic compounds. This exogenous solid has the formula C20H21FN2O and an average molecular weight of 324.39 g/mol. It is classified as a drug (PMC11411717 ) used as an antidepressant and a serotonin uptake inhibitor. Biologically and chemically, it also acts as an inhibitor of EC 3.4.21.26 (prolyl oligopeptidase) and EC 1.8.1.12 (trypanothione-disulfide reductase) (PMC11411717 ). The compound is used in the treatment of depression (PMC10698095 , PMC4457595 ) and major depressive disorder (PMC7902340 ), and it has a therapeutic effect on hypertension (PMC10997981 ). It is associated with an increase in anxiety (PMC12030910 ). Citalopram's antidepressant, antibulimic, and antiobsessive-compulsive actions are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. It blocks serotonin reuptake at the neuronal membrane pump, which enhances the actions of serotonin on 5HT1A autoreceptors. Compared to tricyclic antidepressant drugs, SSRIs like citalopram bind with significantly less affinity to norepinephrine, acetylcholine, and histamine receptors. Recorded protein targets include the sodium-dependent serotonin transporter (SLC6A4), the histamine H1 receptor (HRH1), the muscarinic acetylcholine receptor M1 (CHRM1), the alpha-1A adrenergic receptor (ADRA1A), and solute carrier family 22 member 1 (SLC22A1), among others. Citalopram has been detected in the liver, brain, and platelet tissues. It is found in various sources, including antidepressants, indoor air, food preservation, and household cleaning and consumer products such as tobacco smoke filters, cigar cigarettes, and non-electric simulated smoking devices. It is also recorded in electrical and electronic equipment, including electrodes, antennas, and electrically stimulated smoking devices. Recorded exposure routes include oral and inhalation.
Contaminant Type
  • Amine
  • Antidepressant
  • Antidepressant, Second-Generation
  • Antidepressive Agent
  • Antidepressive Agent, Second-Generation
  • Drug
  • Ether
  • Food Toxin
  • Metabolite
  • Nitrile
  • Organic Compound
  • Organofluoride
  • Selective Serotonin Reuptake Inhibitor
  • Serotonin Uptake Inhibitor
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
CitadurKegg
BonitrileHMDB
CelexaHMDB
Citalopram hydrobromideHMDB
NitalapramHMDB
EscitalopramHMDB
CytalopramHMDB
LexaproHMDB
Escitalopram oxalateHMDB
SeropramHMDB
Chemical FormulaC20H21FN2O
Average Molecular Mass324.392 g/mol
Monoisotopic Mass324.164 g/mol
CAS Registry Number59729-33-8
IUPAC Name1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
Traditional Namerecital
SMILESCN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Brain
  • Liver
  • Platelet
Applications
Biological Roles
Chemical Roles
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point182-183°C
Boiling PointNot Available
SolubilitySparingly soluble
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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000i-6190000000-9c092c583199a2a486efNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0009000000-589e7ae88aee7da0e0bdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0029000000-8fd40dc922da5ab2c8b0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0291000000-c60cbea4e4e6acbb4599Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00l2-0290000000-f2131534473e56b3c8a7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00mk-0390000000-e6cd61150feeca1d2867Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0291000000-ff658bd6b54adccbaf03Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0009000000-67fa40aabd862948aaf3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0129000000-60abdaff2f5d8f72e271Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bt9-0981000000-1eba423765a46f1dd6b9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0980000000-514f2e0bb73903b25b90Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0970000000-f27f46e3a573498d9f9bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0980000000-5ba355c707bc5008c067Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0009000000-a115136f2084cc2a6a47Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0129000000-474ae50db9e74e5a31beNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bt9-0981000000-011dbb85d8e791486397Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0970000000-99aedc452f996b9c9113Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0980000000-c8734dde2a469350af7cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0970000000-cff11d70160f94e8fc2eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0391000000-e7862ea10a18e5771adcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0980000000-d24616414bd7fc5e1182Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0970000000-1c68a33d62afa4612071Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0394000000-f3c86fb3bf5bc7669307Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0390000000-5c227e85878c48f06a42Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0239000000-900cc91bba3c1f9f3674Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0291000000-50d4588c6e576ed9479bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00mk-0390000000-e6cd61150feeca1d2867Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0009000000-a115136f2084cc2a6a47Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0980000000-e702af03bdbc0fcb02b8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00l2-0290000000-f2131534473e56b3c8a7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00mk-0390000000-58f9ff8475a36c60a230Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0009000000-efbd260536f609d80944Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bvi-0693000000-ef7d931ff6cfa54f6e4dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0129000000-bc41beea94961d954402Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0970000000-b2ec8c1a6b6b8ceecc31Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0291000000-26446b333f3824d5bb27Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bt9-0982000000-c86d50409f3430c59646Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00mk-0390000000-5b0d902657a382862c1cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0009000000-19dafc6d4e4b6c9c38d2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bt9-0981000000-deb4c2c5f866c105e3f4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0980000000-edbff0abf39eb8e6d6f6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0129000000-c0a71df4afd3c65a35c2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0029000000-47a2677471959116e49eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0391000000-5f22ead7c72d061a94a6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00l2-0290000000-51a41ee49cd6cfc74c30Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0970000000-37fe214071523d2895eeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0980000000-fb5b278058e3fe97b1c0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0291000000-d2baebfc0c776b757801Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0291000000-ef2c03ec64e0a44ad183Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0970000000-53ecbddf2a196cc02824Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0294000000-c222efdb4ee28dc6f4ccNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0390000000-22e3b0cee05da4f831f1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0970000000-10e5afb00e83fc0290c7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0980000000-4c22977dbba4ed6db0e7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1029000000-b0f10b0f7897ca083ed5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003r-2294000000-5935fccdd160458bb836Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9740000000-7a3a98de78c385feae56Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0019000000-84c6ddc8fad411d8541fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1029000000-d4716f92fec4a098ef2cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0005-5290000000-45334fd57d41c1fadf1aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0009000000-5baf9d241e4712801e87Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-3079000000-3efd9cf0f4fddbeed2c9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1950000000-69ba9b80f8bec9cbe874Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-23521c8b9dc4834c9328Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0091000000-bdb51930294423bb3315Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-1590000000-b821092ee64991ad4390Not AvailableView Spectrum
MSMS Spectrumsplash10-0a4i-9110000000-5b1fde1b7a58929c7f2dNot AvailableView Spectrum
Toxicity Profile
Toxicity Values
Toxicity ValueOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalToxicity RatingReference
234.0 Log mg/kg [130:420]RatLD50oralpredictedNot AvailableNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityThe antidepressant, antiobsessive-compulsive, and antibulimic actions of citalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. Citalopram blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsSymptoms most often accompanying citalopram overdose, alone or in combination with other drugs and/or alcohol, included dizziness, sweating, nausea, vomiting, tremor, somnolence, and sinus tachycardia. In more rare cases, observed symptoms included amnesia, confusion, coma, convulsions, hyperventilation, cyanosis, rhabdomyolysis, and ECG changes (including QTc prolongation, nodal rhythm, ventricular arrhythmia, and very rare cases of torsade de pointes). Acute renal failure has been very rarely reported accompanying overdose. Withdrawal symptoms include flu-like symptoms, insomnia, nausea, imbalance, sensory changes and hyperactivity.
TreatmentEstablish and maintain an airway to ensure adequate ventilation and oxygenation. Gastric evacuation by lavage and use of activated charcoal should be considered. Careful observation and cardiac and vital sign monitoring are recommended, along with general symptomatic and supportive care. Due to the large volume of distribution of citalopram, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. There are no specific antidotes for Celexa. (28)
Health Effects
Health EffectRelationshipDirectionDescriptionReference
hypertensionHas Therapeutic Effect OnNot AvailableA disorder characterized by a pathological increase in blood pressure; a repeatedly elevation in the blood pressure exceeding 140 over 90 mm Hg. (NCI CTCAE)PMC10997981 , PMC10997981
anxietyAssociated With?increaseA disorder characterized by apprehension of danger and dread accompanied by restlessness, tension, tachycardia, and dyspnea unattached to a clearly identifiable stimulus. (NCI CTCAE)PMC12030910
depressionNot AvailableNot AvailableNot AvailablePMC10698095 , PMC4457595
major depressive disorderNot AvailableNot AvailableAn endogenous depression that is characterized by an all-encompassing low mood accompanied by low self-esteem, and by loss of interest or pleasure in normally enjoyable activities. (DO)PMC7902340 , PMC6595891
agitationNot AvailableNot AvailableA disorder characterized by a state of restlessness associated with unpleasant feelings of irritability and tension. (NCI CTCAE)PMC11859965
panic disorderNot AvailableNot AvailableAn anxiety disorder that is characterized by unexpected and repeated episodes of intense fear accompanied by physical symptoms that may include chest pain, heart palpitations, shortness of breath, dizziness, or abdominal distress. (DO)PMC9758520 , PMC11446579
anxiety disorderAssociated With?increaseNot AvailablePMC12030910
anxiety disorderNot AvailableNot AvailableNot AvailablePMC9758520 , PMC11859965
pervasive developmental disorderNot AvailableNot AvailableNot AvailablePMC11446579
depressive disorderNot AvailableNot AvailableNot AvailablePMC10698095 , PMC4217597
BehaviorAssociated With?increaseNot AvailablePMC12030910
Mental HealthAssociated With?increaseNot AvailablePMC12030910
obsessive-compulsive disorderNot AvailableNot AvailableNot AvailablePMC9143978
ApathyNot AvailableNot AvailableNot AvailablePMC11859965
eating disorderNot AvailableNot AvailableNot AvailablePMC9758520
Exposure Sources
Source IDSourceSectorReference
CEDs000010Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.Agriculture & land managementPubChem
CEDs000013Soil?Soil serves as a critical medium for plant growth and sustains various ecological functions; however, it can become a reservoir for synthetic chemical contamination.Agriculture & land managementPMC10927905 , PMC7321103
CEDs000019Indoor air?Indoor air can be a significant reservoir for synthetic chemical contaminants, which often originate from various sources within enclosed environments.Air, dust & atmospheric transportNot Available
CEDs000050Groundwater?Groundwater serves as a vital resource for drinking water and agricultural irrigation but is increasingly susceptible to contamination from synthetic chemicals.Aquatic systems & sedimentsPMC12030910 , PMC12030910
CEDs000051Surface water?Surface water can serve as a significant vector for the introduction of synthetic chemical contaminants into aquatic ecosystems.Aquatic systems & sedimentsPMC12030910 , PMC12030910
CEDs000115Drinking water?Drinking water can be a medium for synthetic chemical contamination, often originating from various industrial processes and agricultural practices.Drinking water & water supplyPMC9403794 , PMC9403794
CEDs000116Tap water?Tap water can be a potential source of synthetic chemical contamination due to various industrial processes and agricultural runoff.Drinking water & water supplyPMC9403794 , PMC7688600
CEDs000377Antidepressants?Antidepressants, a class of synthetic chemicals designed to alleviate symptoms of depression and anxiety, can enter the environment through various pathways, leading to contamination of water systems.Healthcare, pharmaceuticals & veterinary productsNot Available
CEDs000469Sewage sludge?Sewage sludge is a byproduct generated during the treatment of wastewater in municipal and industrial processes.Wastewater, sanitation & biosolidsPMC5981000
CEDs000476Biosolids?Biosolids are nutrient-rich organic materials derived from the treatment of sewage sludge during wastewater management processes.Wastewater, sanitation & biosolidsPMC11381038 , PMC13003354
CEDs000479Effluent?Effluent refers to liquid waste or sewage that is discharged into the environment, typically resulting from industrial processes, municipal wastewater treatment, or agricultural runoff.Wastewater, sanitation & biosolidsPMC9403794 , PMC12531767
CEDs000506Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.Electrical & Electronic EquipmentPubChem
CEDs000511Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.Electrical & Electronic EquipmentPubChem
CEDs000516Electric Hearing Aids?Electric hearing aids are small electronic devices designed to amplify sound for individuals with hearing loss.Electrical & Electronic EquipmentPubChem
CEDs000518Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.Electrical & Electronic EquipmentPubChem
CEDs000519Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.Electrical & Electronic EquipmentPubChem
CEDs000524Hybrid Capacitors?Hybrid capacitors are energy storage devices that combine the properties of electrolytic and supercapacitors, utilizing a combination of electrochemical principles to achieve higher energy density and power density.Electrical & Electronic EquipmentPubChem
CEDs000530Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.Electrical & Electronic EquipmentPubChem
CEDs000545Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.Food, food processing & cookwarePubChem
CEDs000556Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.Household cleaning & consumer productsPubChem
CEDs000559Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.Household cleaning & consumer productsPubChem
CEDs000560Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.Household cleaning & consumer productsPubChem
CEDs000569Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.Household cleaning & consumer productsPubChem
CEDs000580Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.Industrial manufacturing & chemical processingPubChem
CEDs000596Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.Agriculture & land managementPubChem
CEDs000600Herbicides And Algicides?Herbicides and algicides are synthetic chemicals primarily used to control unwanted plants and algae in various environments.Agriculture & land managementPubChem
CEDs000606Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.Agriculture & land managementPubChem
CEDs000610Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.Personal care & cosmeticsPubChem
CEDs000611Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.Personal care & cosmeticsPubChem
CEDs000615Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.Personal care & cosmeticsPubChem
CEDs000617Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.Personal care & cosmeticsPubChem
CEDs000618Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.Personal care & cosmeticsPubChem
CEDs000632Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.Textiles, leather & furnishingsPubChem
CEDs000642Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.Textiles, leather & furnishingsPubChem
CEDs000655Slide Fasteners?Slide fasteners, commonly known as zippers, are mechanical devices used to join two edges of fabric or other materials.Textiles, leather & furnishingsPubChem
CEDs000671Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.Aviation & AerospacePubChem
CEDs000685Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.Building & ConstructionPubChem
CEDs000696Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.Industrial manufacturing & chemical processingPubChem
CEDs000735Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.Defense & military infrastructurePubChem
CEDs000741Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.Paper, pulp & fiber productsPubChem
CEDs000743Sludge Treatment?Sludge treatment involves the processing of waste materials generated from wastewater treatment plants, which often contain a variety of organic and inorganic substances.Wastewater, sanitation & biosolidsPubChem
CEDs000744Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.Wastewater, sanitation & biosolidsPubChem
CEDs01113Clinical SamplesHealthcare, pharmaceuticals & veterinary productsPMC11446579
CEDs01170EggsFood, food processing & cookwarePMC12593334
CEDs02227Raw WaterDrinking water & water supplyPMC10457822 , PMC10457822
CEDs02255WaterAquatic systems & sedimentsPMC6150279 , PMC12863633
CEDs02257WatersAquatic systems & sedimentsPMC10114359
CEDs02264SedimentAquatic systems & sedimentsPMC12424012 , PMC12432068
CEDs02268Water SamplesAquatic systems & sedimentsPMC9403794 , PMC12863633
CEDs02289StreamAquatic systems & sedimentsPMC9431852
CEDs02319Lake WaterAquatic systems & sedimentsPMC5306312
CEDs02324Freshwater EnvironmentAquatic systems & sedimentsPMC9758520
CEDs02532Bed SedimentsAquatic systems & sedimentsPMC9431852
CEDs03009Waste WaterWastewater, sanitation & biosolidsPMC10698095
CEDs03014SewageWastewater, sanitation & biosolidsPMC11759868 , PMC11759868
CEDs03017SludgeWastewater, sanitation & biosolidsPMC8930529 , PMC11602849
CEDs03021Wastewater Treatment PlantWastewater, sanitation & biosolidsPMC11958392
CEDs03028Wastewater EffluentWastewater, sanitation & biosolidsPMC12424012
CEDs03039Influent WastewaterWastewater, sanitation & biosolidsPMC10698095
CEDs03040Wastewater SludgeWastewater, sanitation & biosolidsPMC8226068
CEDs03043WWTPsWastewater, sanitation & biosolidsPMC10114359
CEDs03071Effluent WastewaterWastewater, sanitation & biosolidsPMC10698095
CEDs03091WWTPs effluentsWastewater, sanitation & biosolidsPMC11570933
Pathways
5 pathwaysPathway Source: PathBank
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)
Prediction Confidence Score
0.632
Applicability Domain
1.0
Statistical Significance
5.10e-04
Supporting Reference Compounds
593
E-value
3.97031
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.625
Applicability Domain
1.0
Statistical Significance
5.30e-04
Supporting Reference Compounds
297
E-value
4.12601
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.622
Applicability Domain
1.0
Statistical Significance
4.10e-04
Supporting Reference Compounds
203
E-value
3.19182
Click to view 3D structureTransporterQ63380Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.45
Applicability Domain
1.0
Statistical Significance
2.70e-04
Supporting Reference Compounds
54
E-value
2.10193
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)
Prediction Confidence Score
0.424
Applicability Domain
1.0
Statistical Significance
0.0199
Supporting Reference Compounds
1498
E-value
155.231
Histamine H1 receptor structureClick to view 3D structureHistamine H1 receptorP35367HumansPredicted (SEA)
Prediction Confidence Score
0.39
Applicability Domain
1.0
Statistical Significance
0.0105
Supporting Reference Compounds
507
E-value
82.0531
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)
Prediction Confidence Score
0.386
Applicability Domain
1.0
Statistical Significance
0.0065
Supporting Reference Compounds
451
E-value
50.9912
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)
Prediction Confidence Score
0.384
Applicability Domain
1.0
Statistical Significance
0.0155
Supporting Reference Compounds
823
E-value
120.355
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)
Prediction Confidence Score
0.38
Applicability Domain
1.0
Statistical Significance
0.0113
Supporting Reference Compounds
686
E-value
87.8918
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)
Prediction Confidence Score
0.38
Applicability Domain
1.0
Statistical Significance
0.0117
Supporting Reference Compounds
536
E-value
90.7722
Click to view 3D structureAlpha-1A adrenergic receptorP43140Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.379
Applicability Domain
1.0
Statistical Significance
0.0063
Supporting Reference Compounds
208
E-value
48.9672
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)
Prediction Confidence Score
0.378
Applicability Domain
1.0
Statistical Significance
0.0169
Supporting Reference Compounds
562
E-value
131.487
Click to view 3D structureNorepinephrine transporterQ9WTR4Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.373
Applicability Domain
1.0
Statistical Significance
0.0031
Supporting Reference Compounds
112
E-value
23.8997
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)
Prediction Confidence Score
0.373
Applicability Domain
1.0
Statistical Significance
0.0062
Supporting Reference Compounds
258
E-value
48.4222
Click to view 3D structureAlpha-1B adrenergic receptorP15823Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.37
Applicability Domain
1.0
Statistical Significance
0.0035
Supporting Reference Compounds
130
E-value
27.1694
Click to view 3D structureSigma non-opioid intracellular receptor 1Q9R0C9Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.367
Applicability Domain
1.0
Statistical Significance
0.0056
Supporting Reference Compounds
207
E-value
43.9848
Click to view 3D structureSigma intracellular receptor 2Q5U3Y7Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.362
Applicability Domain
1.0
Statistical Significance
0.0059
Supporting Reference Compounds
110
E-value
46.0867
Click to view 3D structureSodium-dependent serotonin transporterQ60857Mus musculusPredicted (SEA)
Prediction Confidence Score
0.357
Applicability Domain
1.0
Statistical Significance
4.20e-04
Supporting Reference Compounds
20
E-value
3.26967
Click to view 3D structureSodium-dependent noradrenaline transporterO55192Mus musculusPredicted (SEA)
Prediction Confidence Score
0.356
Applicability Domain
1.0
Statistical Significance
1.80e-04
Supporting Reference Compounds
15
E-value
1.40129
Click to view 3D structureSodium-dependent dopamine transporterQ61327MousePredicted (SEA)
Prediction Confidence Score
0.34
Applicability Domain
1.0
Statistical Significance
6.40e-04
Supporting Reference Compounds
18
E-value
4.98235
Click to view 3D structureC-X-C chemokine receptor type 2P35344Oryctolagus cuniculusPredicted (SEA)
Prediction Confidence Score
0.258
Applicability Domain
0.268 Low confidence
Statistical Significance
0.0013
Supporting Reference Compounds
2
E-value
10.4318
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)
Prediction Confidence Score
0.24
Applicability Domain
0.281 Low confidence
Statistical Significance
0.3436
Supporting Reference Compounds
861
E-value
2675.05
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)
Prediction Confidence Score
0.239
Applicability Domain
0.268 Low confidence
Statistical Significance
0.5852
Supporting Reference Compounds
1130
E-value
4555.5
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP08909RatPredicted (SEA)
Prediction Confidence Score
0.237
Applicability Domain
0.333
Statistical Significance
0.1287
Supporting Reference Compounds
185
E-value
1001.92
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)
Prediction Confidence Score
0.234
Applicability Domain
0.25 Low confidence
Statistical Significance
0.3161
Supporting Reference Compounds
506
E-value
2460.97
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansKnownNot Available
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansKnownNot Available
Click to view 3D structureCytochrome P450 1A1P00185RatKnownNot Available
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansKnownNot Available
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansKnownThe antidepressant, antiobsessive-compulsive, and antibulimic actions of Citalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. Citalopram blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansKnownNot Available
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansKnownNot Available
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansKnownNot Available
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansKnownNot Available
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansKnownNot Available
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansKnownNot Available
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansKnownNot Available
5-hydroxytryptamine receptor 1D structureClick to view 3D structure5-hydroxytryptamine receptor 1DP28221HumansKnownNot Available
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansKnownNot Available
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansKnownNot Available
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansKnownNot Available
Histamine H1 receptor structureClick to view 3D structureHistamine H1 receptorP35367HumansKnownNot Available
Solute carrier family 22 member 1 structureClick to view 3D structureSolute carrier family 22 member 1O15245HumansKnownNot Available
Concentrations
StatusValueUnitSample LocationReference
Detected and Semi Quantified210ng/LBioggio,Lugano
Detected and Semi Quantified76ng/LBussigny-prés-Lausanne
Detected and Semi Quantified310ng/LHallau,Klettgau
Detected and Semi Quantified300ng/LThal,Altenrhein
Detected and Semi Quantified490ng/LUetendorf,Thun
Detected and Semi Quantified280ng/LVernier,Aïre
Detected and Semi Quantified800ng/LWinterthur
Detected and Semi Quantified170ng/LWerdhölzli,Zürich
Detected and Semi Quantified950ng/LSchönau,Zug
Detected and Semi Quantified600ng/LAffoltern,Zwillikon
External Links
DrugBank IDDB00215
HMDB IDHMDB0005038
FooDB IDFDB023605
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID1781
PDB IDNot Available
Wikipedia LinkCitalopram
Chemspider ID2669
ChEBI ID77397
PubChem Compound ID2771
Kegg Compound IDC07572
YMDB IDNot Available
ECMDB IDM2MDB005092
References
Synthesis Reference

Hans Petersen, “Method for the preparation of citalopram.” U.S. Patent US6229026, issued December, 1992.

MSDSLink
General References
  1. Sindrup SH, Bjerre U, Dejgaard A, Brosen K, Aaes-Jorgensen T, Gram LF: The selective serotonin reuptake inhibitor citalopram relieves the symptoms of diabetic neuropathy. Clin Pharmacol Ther. 1992 Nov;52(5):547-52. [PubMed: 1424428]
  2. Atmaca M, Kuloglu M, Tezcan E, Semercioz A: The efficacy of citalopram in the treatment of premature ejaculation: a placebo-controlled study. Int J Impot Res. 2002 Dec;14(6):502-5. [PubMed: 12494286]
  3. Andersen G, Vestergaard K, Riis JO: Citalopram for post-stroke pathological crying. Lancet. 1993 Oct 2;342(8875):837-9. [PubMed: 8104273]
  4. Clayton A, Keller A, McGarvey EL: Burden of phase-specific sexual dysfunction with SSRIs. J Affect Disord. 2006 Mar;91(1):27-32. Epub 2006 Jan 20. [PubMed: 16430968]
  5. Baumann P: Pharmacology and pharmacokinetics of citalopram and other SSRIs. Int Clin Psychopharmacol. 1996 Mar;11 Suppl 1:5-11. [PubMed: 8732438]
  6. Hyttel J, Bogeso KP, Perregaard J, Sanchez C: The pharmacological effect of citalopram residues in the (S)-(+)-enantiomer. J Neural Transm Gen Sect. 1992;88(2):157-60. [PubMed: 1632943]
  7. Caccia S: Metabolism of the newer antidepressants. An overview of the pharmacological and pharmacokinetic implications. Clin Pharmacokinet. 1998 Apr;34(4):281-302. [PubMed: 9571301]
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  9. Blardi P, de Lalla A, Urso R, Auteri A, Dell'Erba A, Bossini L, Castrogiovanni P: Activity of citalopram on adenosine and serotonin circulating levels in depressed patients. J Clin Psychopharmacol. 2005 Jun;25(3):262-6. [PubMed: 15876907]
  10. Bhagwagar Z, Hafizi S, Cowen PJ: Acute citalopram administration produces correlated increases in plasma and salivary cortisol. Psychopharmacology (Berl). 2002 Aug;163(1):118-20. Epub 2002 Jun 27. [PubMed: 12185409]
  11. Nikisch G, Mathe AA, Czernik A, Eap CB, Jimenez-Vasquez P, Brawand-Amey M, Baumann P: Stereoselective metabolism of citalopram in plasma and cerebrospinal fluid of depressive patients: relationship with 5-HIAA in CSF and clinical response. J Clin Psychopharmacol. 2004 Jun;24(3):283-90. [PubMed: 15118482]
  12. Anastos N, McIntyre IM, Lynch MJ, Drummer OH: Postmortem concentrations of citalopram. J Forensic Sci. 2002 Jul;47(4):882-4. [PubMed: 12137000]
  13. Horak EL, Jenkins AJ: Postmortem tissue distribution of olanzapine and citalopram in a drug intoxication. J Forensic Sci. 2005 May;50(3):679-81. [PubMed: 15932107]
  14. Lapatto-Reiniluoto O, Kivisto KT, Neuvonen PJ: Effect of activated charcoal alone or given after gastric lavage in reducing the absorption of diazepam, ibuprofen and citalopram. Br J Clin Pharmacol. 1999 Aug;48(2):148-53. [PubMed: 10417490]
  15. Worm K, Dragsholt C, Simonsen KW, Kringsholm B: [Citalopram in forensic samples. Citalopram concentrations in samples from legal autopsies and from living persons in connection with traffic accidents or cases of violence in Denmark 1989-1996]. Ugeskr Laeger. 1999 Jul 26;161(30):4291-2. [PubMed: 10439690]
  16. Jensen PN, Olesen OV, Bertelsen A, Linnet K: Citalopram and desmethylcitalopram concentrations in breast milk and in serum of mother and infant. Ther Drug Monit. 1997 Apr;19(2):236-9. [PubMed: 9108657]
  17. Schmidt K, Olesen OV, Jensen PN: Citalopram and breast-feeding: serum concentration and side effects in the infant. Biol Psychiatry. 2000 Jan 15;47(2):164-5. [PubMed: 10664835]
  18. Rochat B, Kosel M, Boss G, Testa B, Gillet M, Baumann P: Stereoselective biotransformation of the selective serotonin reuptake inhibitor citalopram and its demethylated metabolites by monoamine oxidases in human liver. Biochem Pharmacol. 1998 Jul 1;56(1):15-23. [PubMed: 9698084]
  19. Kristoffersen L, Bugge A, Lundanes E, Slordal L: Simultaneous determination of citalopram, fluoxetine, paroxetine and their metabolites in plasma and whole blood by high-performance liquid chromatography with ultraviolet and fluorescence detection. J Chromatogr B Biomed Sci Appl. 1999 Nov 12;734(2):229-46. [PubMed: 10595721]
  20. Nordeng H, Bergsholm YK, Bohler E, Spigset O: [The transfer of selective serotonin reuptake inhibitors to human milk]. Tidsskr Nor Laegeforen. 2001 Jan 20;121(2):199-203. [PubMed: 11475200]
  21. Plenge P, Mellerup ET: [3H]citalopram binding to brain and platelet membranes of human and rat. J Neurochem. 1991 Jan;56(1):248-52. [PubMed: 1824783]
  22. Nikisch G, Mathe AA, Czernik A, Thiele J, Bohner J, Eap CB, Agren H, Baumann P: Long-term citalopram administration reduces responsiveness of HPA axis in patients with major depression: relationship with S-citalopram concentrations in plasma and cerebrospinal fluid (CSF) and clinical response. Psychopharmacology (Berl). 2005 Oct;181(4):751-60. Epub 2005 Sep 29. [PubMed: 15988572]
  23. Spigset O, Hagg S, Stegmayr B, Dahlqvist R: Citalopram pharmacokinetics in patients with chronic renal failure and the effect of haemodialysis. Eur J Clin Pharmacol. 2000 Dec;56(9-10):699-703. [PubMed: 11214779]
  24. Anderer P, Saletu B, Semlitsch HV, Pascual-Marqui RD: Perceptual and cognitive event-related potentials in neuropsychopharmacology: methodological aspects and clinical applications (pharmaco-ERP topography and tomography). Methods Find Exp Clin Pharmacol. 2002;24 Suppl C:121-37. [PubMed: 12575494]
  25. Kosel M, Gnerre C, Voirol P, Amey M, Rochat B, Bouras C, Testa B, Baumann P: In vitro biotransformation of the selective serotonin reuptake inhibitor citalopram, its enantiomers and demethylated metabolites by monoamine oxidase in rat and human brain preparations. Mol Psychiatry. 2002;7(2):181-8. [PubMed: 11840311]
  26. Spigset O, Wilhelmsson C, Mjorndal T, Eriksson S: Low serum sodium concentrations during treatment with citalopram in elderly patients: relationship to serum citalopram levels and to platelet serotonin 5-HT2A receptor status. J Clin Psychopharmacol. 2000 Oct;20(5):582-4. [PubMed: 11001247]
  27. Drugs.com - http://www.drugs.com/cons/Citalopram.html
  28. RxList: The Internet Drug Index (2009). - http://www.rxlist.com/
  29. FDA label