Trazodone (CED0003085)

Record Information
Version1.0
Creation Date2009-07-21 20:27:21 UTC
Update Date2026-05-14 16:45:14 UTC
Accession NumberCHEM002241
Identification
Common NameTrazodone
ClassSmall Molecule
Description
Trazodone belongs to the piperazines, a subclass of diazinanes within the organic compounds. This exogenous compound has the formula C19H22ClN5O and an average molecular weight of 371.86 g/mol. At room temperature, it exists as a solid. It is used as an antidepressant, sedative, and anxiolytic drug, and it functions biologically as a serotonin uptake inhibitor, H1-receptor antagonist, and adrenergic antagonist. The compound targets several proteins, including the sodium-dependent serotonin transporter (SLC6A4), the sodium-dependent noradrenaline transporter (SLC6A2), the 5-hydroxytryptamine receptor 2A (HTR2A), and the alpha-1A adrenergic receptor (ADRA1A). It also acts as a partial agonist of the 5-hydroxytryptamine receptor 2C (HTR2C) and targets muscarinic acetylcholine receptors M1, M2, and M4. Trazodone binds at the 5-HT2 receptor, acting as a serotonin antagonist at low doses and a serotonin agonist at high doses. Its antidepressant activity likely results from the inhibition of the serotonin reuptake pump at the presynaptic neuronal membrane, though long-term use may affect postsynaptic neuronal receptor binding sites. The sedative effect is likely caused by modest alpha-adrenergic blocking action. Trazodone is found in antidepressants and has been recorded in drinking water, food preservation, tents or canopies, and various electronic and consumer products, including discharge lamps, electric switches, ash trays, and tobacco smoke filters. The recorded exposure route for this compound is oral.
Contaminant Type
  • Amine
  • Anti-Anxiety Agent
  • Antidepressant, Second-Generation
  • Antidepressive Agent, Second-Generation
  • Drug
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Serotonin Uptake Inhibitor
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
2-(3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneChEBI
TrazodonaChEBI
TrazodonumChEBI
TritticoKegg
Aventis brand OF trazodone hydrochlorideHMDB
DesyrelHMDB
Farma lepori brand OF trazodone hydrochlorideHMDB
Gen-trazodoneHMDB
Genpharm brand OF trazodone hydrochlorideHMDB
Novopharm brand OF trazodone hydrochlorideHMDB
Nu pharm brand OF trazodone hydrochlorideHMDB
Ratiopharm brand OF trazodone hydrochlorideHMDB
Searle brand OF trazodone hydrochlorideHMDB
Trazodon-neuraxpharmHMDB
Apo-trazodoneHMDB
Apotex brand OF trazodone hydrochlorideHMDB
Boehringer ingelheim brand OF trazodone hydrochlorideHMDB
Bristol myers squibb brand OF trazodone hydrochlorideHMDB
Bristol-myers squibb brand OF trazodone hydrochlorideHMDB
Gen trazodoneHMDB
MolipaxinHMDB
Sidmark brand OF trazodone hydrochlorideHMDB
TradozoneHMDB
Trazodon hexalHMDB
Trazodone hydrochlorideHMDB
Ratio trazodoneHMDB
Apo trazodoneHMDB
DepraxHMDB
Novo-trazodoneHMDB
Nu trazodoneHMDB
Nu-trazodoneHMDB
Pharmascience brand OF trazodone hydrochlorideHMDB
ThombranHMDB
Neuraxpharm brand OF trazodone hydrochlorideHMDB
Apothecon brand OF trazodone hydrochlorideHMDB
Aventis pharma brand OF trazodone hydrochlorideHMDB
Hexal brand OF trazodone hydrochlorideHMDB
Novo trazodoneHMDB
Nu-pharm brand OF trazodone hydrochlorideHMDB
PMS TrazodoneHMDB
PMS-TrazodoneHMDB
Trazodon neuraxpharmHMDB
TrazonHMDB
Ratio-trazodoneHMDB
RatioTrazodoneHMDB
TrazodonNeuraxpharmHMDB
Chemical FormulaC19H22ClN5O
Average Molecular Mass371.864 g/mol
Monoisotopic Mass371.151 g/mol
CAS Registry Number19794-93-5
IUPAC Name2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one
Traditional Nametrazodone
SMILESClC1=CC=CC(=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC1
InChI IdentifierInChI=1S/C19H22ClN5O/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25/h1-3,5-7,9,15H,4,8,10-14H2
InChI KeyPHLBKPHSAVXXEF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • Phenylpiperazine
  • N-arylpiperazine
  • Aryl 1,2,4-triazol-3-one
  • Triazolopyridine
  • Tertiary aliphatic/aromatic amine
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Pyridinone
  • Chlorobenzene
  • N-alkylpiperazine
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Monocyclic benzene moiety
  • Benzenoid
  • 1,2,4-triazole
  • Azole
  • Heteroaromatic compound
  • Triazole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point87°C
Boiling PointNot Available
SolubilitySparigly soluble
Predicted Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP2.68ALOGPS
logP3.13ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)7.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area42.39 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity105.88 m³·mol⁻¹ChemAxon
Polarizability40.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4j-3940000000-a9996f74a013c4cd5f34Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0609000000-cee74b5bf3182c2aa324Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-6900000000-cad4ab75befff3f2968bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9400000000-c7d8f0dfcdffc01eea38Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-1900000000-28ba21055e54b4402211Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-6fb990f5da8a065e9e2dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004j-0900000000-3e00b6f236166b87e556Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-389ead4eddc071685054Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00b9-0905000000-7559d512fbf6d562d524Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0902000000-32913e34f1b8199d47e2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004j-0900000000-eba2f098618563ae8d8dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0209000000-df47170d3861120bdd95Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-bcfc1f78608d8da92b69Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9400000000-e57c89e0b5532e2d9949Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ba-0904000000-6d3af981b3cc1292370aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0409000000-aa395fcbb17de632c6bdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-009j-3943000000-2a70b3bfe44c6f0cbc7bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f7d-6910000000-98fd05d57a2cfaca1e18Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1509000000-86e48f5bf6cb797c7455Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-4903000000-dbd293226ccdf09ec683Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-053r-2900000000-cc4d58e26d8dc2a62148Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-6eafab677fc7a5bcdc94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0429000000-7ff66c2ff10e98b15b9bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6x-2935000000-39b0f2302534fa91975fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-46b6e1f93b93a9142b29Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1009000000-fb123f08ae47e01d90aaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-9764000000-16579101709849df0f45Not AvailableView Spectrum
MSMS Spectrumsplash10-0a4i-7980000000-5d2bde624fdd9a946993Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityTrazodone binds at 5-HT2 receptor, it acts as a serotonin agonist at high doses and a serotonin antagonist at low doses. Like fluoxetine, trazodone's antidepressant activity likely results from blockage of serotonin reuptake by inhibiting serotonin reuptake pump at the presynaptic neuronal membrane. If used for long time periods, postsynaptic neuronal receptor binding sites may also be affected. The sedative effect of trazodone is likely the result of alpha-adrenergic blocking action and modest histamine blockade at H1 receptor. It weakly blocks presynaptic alpha2-adrenergic receptors and strongly inhibits postsynaptic alpha1 receptors. Trazodone does not affect the reuptake of norepinephrine or dopamine within the CNS.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentThere is no specific antidote for Trazodone. Treatment should be symptomatic and supportive in the case of hypotension or excessive sedation. Any patient suspected of having taken an overdose should have the stomach emptied by gastric lavage. Forced diuresis may be useful in facilitating elimination of the drug. (10)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
96.0mg/kgNot AvailableMouseLD50IntravenousexperimentalA308
772.0Log mg/kg[430:1400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
377AntidepressantsHealthcare, pharmaceuticals & veterinary productsNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
622Game AccessoriesRecreation & sports surfacesNot Available
627Roulette GamesRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
Pathways
5 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)6.69503
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)4.51525
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)3.19182
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)14.1686
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)11.0546
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)22.4206
Histamine H1 receptor structureClick to view 3D structureHistamine H1 receptorP35367HumansPredicted (SEA)5.68299
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)9.809
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)9.10836
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)24.1333
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)7.78492
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)5.0602
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)5.91654
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)5.13805
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)18.5281
Click to view 3D structureAlpha-1A adrenergic receptorP43140Rattus norvegicusPredicted (SEA)12.5337
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)56.9078
Click to view 3D structure5-hydroxytryptamine receptor 1BP28564Rattus norvegicusPredicted (SEA)7.31783
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)37.7569
Click to view 3D structureAlpha-1B adrenergic receptorP15823Rattus norvegicusPredicted (SEA)3.73676
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)27.3251
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)32.2296
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)33.2416
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)25.0674
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)21.0971
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansKnownTrazodone binds at 5-HT2 receptor, it acts as a serotonin agonist at high doses and a serotonin antagonist at low doses. Like fluoxetine, trazodone's antidepressant activity likely results from blockage of serotonin reuptake by inhibiting serotonin reuptake pump at the presynaptic neuronal membrane. If used for long time periods, postsynaptic neuronal receptor binding sites may also be affected. The sedative effect of trazodone is likely the result of alpha-adrenergic blocking action and modest histamine blockade at H1 receptor. It weakly blocks presynaptic alpha2-adrenergic receptors and strongly inhibits postsynaptic alpha1 receptors. Trazodone does not affect the reuptake of norepinephrine or dopamine within the CNS.
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansKnownNot Available
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansKnownTrazodone binds at 5-HT2 receptor, it acts as a serotonin agonist at high doses and a serotonin antagonist at low doses. Like fluoxetine, trazodone's antidepressant activity likely results from blockage of serotonin reuptake by inhibiting serotonin reuptake pump at the presynaptic neuronal membrane. If used for long time periods, postsynaptic neuronal receptor binding sites may also be affected. The sedative effect of trazodone is likely the result of alpha-adrenergic blocking action and modest histamine blockade at H1 receptor. It weakly blocks presynaptic alpha2-adrenergic receptors and strongly inhibits postsynaptic alpha1 receptors. Trazodone does not affect the reuptake of norepinephrine or dopamine within the CNS.
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansKnownTrazodone binds at 5-HT2 receptor, it acts as a serotonin agonist at high doses and a serotonin antagonist at low doses. Like fluoxetine, trazodone's antidepressant activity likely results from blockage of serotonin reuptake by inhibiting serotonin reuptake pump at the presynaptic neuronal membrane. If used for long time periods, postsynaptic neuronal receptor binding sites may also be affected. The sedative effect of trazodone is likely the result of alpha-adrenergic blocking action and modest histamine blockade at H1 receptor. It weakly blocks presynaptic alpha2-adrenergic receptors and strongly inhibits postsynaptic alpha1 receptors. Trazodone does not affect the reuptake of norepinephrine or dopamine within the CNS.
Histamine H1 receptor structureClick to view 3D structureHistamine H1 receptorP35367HumansKnownTrazodone binds at 5-HT2 receptor, it acts as a serotonin agonist at high doses and a serotonin antagonist at low doses. Like fluoxetine, trazodone's antidepressant activity likely results from blockage of serotonin reuptake by inhibiting serotonin reuptake pump at the presynaptic neuronal membrane. If used for long time periods, postsynaptic neuronal receptor binding sites may also be affected. The sedative effect of trazodone is likely the result of alpha-adrenergic blocking action and modest histamine blockade at H1 receptor. It weakly blocks presynaptic alpha2-adrenergic receptors and strongly inhibits postsynaptic alpha1 receptors. Trazodone does not affect the reuptake of norepinephrine or dopamine within the CNS.
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansKnownTrazodone binds at 5-HT2 receptor, it acts as a serotonin agonist at high doses and a serotonin antagonist at low doses. Like fluoxetine, trazodone's antidepressant activity likely results from blockage of serotonin reuptake by inhibiting serotonin reuptake pump at the presynaptic neuronal membrane. If used for long time periods, postsynaptic neuronal receptor binding sites may also be affected. The sedative effect of trazodone is likely the result of alpha-adrenergic blocking action and modest histamine blockade at H1 receptor. It weakly blocks presynaptic alpha2-adrenergic receptors and strongly inhibits postsynaptic alpha1 receptors. Trazodone does not affect the reuptake of norepinephrine or dopamine within the CNS.
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansKnownTrazodone binds at 5-HT2 receptor, it acts as a serotonin agonist at high doses and a serotonin antagonist at low doses. Like fluoxetine, trazodone's antidepressant activity likely results from blockage of serotonin reuptake by inhibiting serotonin reuptake pump at the presynaptic neuronal membrane. If used for long time periods, postsynaptic neuronal receptor binding sites may also be affected. The sedative effect of trazodone is likely the result of alpha-adrenergic blocking action and modest histamine blockade at H1 receptor. It weakly blocks presynaptic alpha2-adrenergic receptors and strongly inhibits postsynaptic alpha1 receptors. Trazodone does not affect the reuptake of norepinephrine or dopamine within the CNS.
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansKnownNot Available
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansKnownTrazodone binds at 5-HT2 receptor, it acts as a serotonin agonist at high doses and a serotonin antagonist at low doses. Like fluoxetine, trazodone's antidepressant activity likely results from blockage of serotonin reuptake by inhibiting serotonin reuptake pump at the presynaptic neuronal membrane. If used for long time periods, postsynaptic neuronal receptor binding sites may also be affected. The sedative effect of trazodone is likely the result of alpha-adrenergic blocking action and modest histamine blockade at H1 receptor. It weakly blocks presynaptic alpha2-adrenergic receptors and strongly inhibits postsynaptic alpha1 receptors. Trazodone does not affect the reuptake of norepinephrine or dopamine within the CNS.
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansKnownNot Available
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansKnownTrazodone binds at 5-HT2 receptor, it acts as a serotonin agonist at high doses and a serotonin antagonist at low doses. Like fluoxetine, trazodone's antidepressant activity likely results from blockage of serotonin reuptake by inhibiting serotonin reuptake pump at the presynaptic neuronal membrane. If used for long time periods, postsynaptic neuronal receptor binding sites may also be affected. The sedative effect of trazodone is likely the result of alpha-adrenergic blocking action and modest histamine blockade at H1 receptor. It weakly blocks presynaptic alpha2-adrenergic receptors and strongly inhibits postsynaptic alpha1 receptors. Trazodone does not affect the reuptake of norepinephrine or dopamine within the CNS.
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansKnownNot Available
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansKnownNot Available
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansKnownNot Available
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00656
HMDB IDHMDB0014794
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTrazodone
Chemspider ID5332
ChEBI ID9654
PubChem Compound ID5533
Kegg Compound IDC07156
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. Jauch R, Kopitar Z, Prox A, Zimmer A: [Pharmacokinetics and metabolism of trazodone in man (author's transl)]. Arzneimittelforschung. 1976;26(11):2084-9.
2. Marek GJ, McDougle CJ, Price LH, Seiden LS: A comparison of trazodone and fluoxetine: implications for a serotonergic mechanism of antidepressant action. Psychopharmacology (Berl). 1992;109(1-2):2-11.
3. Otani K, Yasui N, Kaneko S, Ishida M, Ohkubo T, Osanai T, Sugawara K, Fukushima Y: Trazodone treatment increases plasma prolactin concentrations in depressed patients. Int Clin Psychopharmacol. 1995 Jun;10(2):115-7.
4. Rotzinger S, Fang J, Baker GB: Trazodone is metabolized to m-chlorophenylpiperazine by CYP3A4 from human sources. Drug Metab Dispos. 1998 Jun;26(6):572-5.
5. Saletu-Zyhlarz GM, Abu-Bakr MH, Anderer P, Gruber G, Mandl M, Strobl R, Gollner D, Prause W, Saletu B: Insomnia in depression: differences in objective and subjective sleep and awakening quality to normal controls and acute effects of trazodone. Prog Neuropsychopharmacol Biol Psychiatry. 2002 Feb;26(2):249-60.
6. Fink HA, MacDonald R, Rutks IR, Wilt TJ: Trazodone for erectile dysfunction: a systematic review and meta-analysis. BJU Int. 2003 Sep;92(4):441-6.
7. Kalgutkar AS, Henne KR, Lame ME, Vaz AD, Collin C, Soglia JR, Zhao SX, Hop CE: Metabolic activation of the nontricyclic antidepressant trazodone to electrophilic quinone-imine and epoxide intermediates in human liver microsomes and recombinant P4503A4. Chem Biol Interact. 2005 Jun 30;155(1-2):10-20. Epub 2005 Apr 18.