Bupropion (CED0002080)

Record Information
Version1.0
Creation Date2009-07-21 20:28:29 UTC
Update Date2026-05-14 16:58:18 UTC
SynCED IDCED0002080
Secondary Accession Numbers
  • CHEM002358
  • T3D2999
Identification
Common NameBupropion
ClassSmall Molecule
Description
Bupropion is an exogenous organic compound with the formula C13H18ClNO and an average molecular weight of 239.74 g/mol. It exists as a solid at room temperature. Bupropion belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. It is used as an antidepressant and as an aid to smoking cessation treatment. The compound is detected in the liver and brain. Recorded exposure routes include oral administration and the occlusive dressing technique. Bupropion is a selective catecholamine reuptake inhibitor targeting norepinephrine and dopamine, with only a small effect on serotonin reuptake. It does not inhibit MAO. Its antidepressant effect is considered to be mediated by its dopaminergic and noradrenergic action. Specifically, it selectively inhibits the neuronal reuptake of dopamine, norepinephrine, and serotonin; however, its blockade of norepinephrine and serotonin reuptake at the neuronal membrane is weaker than that of tricyclic antidepressants, while its actions on dopaminergic systems are more significant than those of amitriptyline or imipramine. An increase in dopamine at neuronal sites may reduce the urge to smoke and nicotine cravings, while an increase in norepinephrine may attenuate nicotine withdrawal symptoms. The compound acts as a competitive alpha-3-beta-4-nicotinic antagonist, an action that correlates with the interruption of addiction. Its recorded protein targets include the sodium-dependent dopamine transporter (SLC6A3), sodium-dependent noradrenaline transporter (SLC6A2), sodium-dependent serotonin transporter (SLC6A4), and neuronal acetylcholine receptor subunits alpha-3 (CHRNA3), alpha-4 (CHRNA4), and alpha-7 (CHRNA7), among nine other proteins. It is found in antidepressants, antiobesity preparations, food preservation, and various consumer products including cigarettes and electrically stimulated smoking devices.
Contaminant Type
  • Amine
  • Antidepressant
  • Antidepressant, Second-Generation
  • Antidepressive Agent, Second-Generation
  • Dopamine Uptake Inhibitor
  • Drug
  • Ester
  • Food Toxin
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
(+-)-BupropionHMDB
AmfebutamonaHMDB
AmfebutamoneHMDB, MeSH
AmfebutamonumHMDB
WellbatrinHMDB
WellbutrinHMDB, MeSH
ZybanHMDB
Bupropion hydrochlorideMeSH, HMDB
Bupropion, (+-)-isomerMeSH, HMDB
glaxo Wellcome brand 1 OF bupropion hydrochlorideMeSH, HMDB
glaxo Wellcome brand 3 OF bupropion hydrochlorideMeSH, HMDB
Zyban (anti-smoking)MeSH, HMDB
GlaxoSmithKline brand 2 OF bupropion hydrochlorideMeSH, HMDB
(+-)-1-(3-Chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanoneMeSH, HMDB
Esteve brand OF bupropion hydrochlorideMeSH, HMDB
glaxo Wellcome brand 2 OF bupropion hydrochlorideMeSH, HMDB
Bupropion hydrochloride, (+-)-isomerMeSH, HMDB
GlaxoSmithKline brand 1 OF bupropion hydrochlorideMeSH, HMDB
QuomenMeSH, HMDB
ZyntabacMeSH, HMDB
Zyban (bupropion)MeSH, HMDB
Chemical FormulaC13H18ClNO
Average Molecular Mass239.741 g/mol
Monoisotopic Mass239.108 g/mol
CAS Registry Number34841-39-9
IUPAC Name2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
Traditional Namebupropion
SMILESCC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1
InChI IdentifierInChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3
InChI KeySNPPWIUOZRMYNY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Phenylpropane
  • Benzoyl
  • Aryl alkyl ketone
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Alpha-aminoketone
  • Secondary aliphatic amine
  • Secondary amine
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Brain
  • Liver
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point233-234°C
Boiling PointNot Available
Solubility312 mg/ml
Predicted Properties
PropertyValueSource
Water Solubility0.069 g/LALOGPS
logP3.28ALOGPS
logP3.27ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)18.29ChemAxon
pKa (Strongest Basic)8.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.7 m³·mol⁻¹ChemAxon
Polarizability25.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000l-5900000000-1b5fb2e947791614a61dNot 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 Spectrumsplash10-001i-0910000000-fa2592b7296c7561333cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-c10af1c8e3619fe0bffcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0490000000-55448af4d9a8ce866a88Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-2883ba18321a8b8228a1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0159-0900000000-7d6cad849706146ddab3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0159-0900000000-0fca8999746b69ee4fc1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-b64f8d2b50bede574f63Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-2edefa63d5f6f1b08db7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0490000000-b8ea1de058a84547700dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0910000000-6f471b9150fb1b7f6fccNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0159-0900000000-cc966137ee3283828af7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lr-0900000000-7f86f38f740aa41b244bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-e7f2cfdbabbd35a9b643Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-4daf0e10db1e5f2750bfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-f77a450be176593153d2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00m0-0910000000-d2eb7265b058766459c9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0910000000-fa2592b7296c7561333cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-4d831e97d7e7dfff141bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lr-0900000000-65c6a707c92719eb037bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0159-0900000000-3c1fb63e67cfd4a3c99dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0490000000-b0c19e8ab1852fba48f9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0490000000-9431c78306c121e34a0dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-c29bde37f5f187ee09d6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-f5256cb7a96a81d33329Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0910000000-ae8e8ab9b204e47fd64cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-0367224b40fd0b08c0b0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0159-0900000000-57c00d94b20f251cc424Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0159-0900000000-98c2bbefb1505b3223e2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-b1da11a9bc8cda7cdd3bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-ec9116c895ebc67a46d2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-09ac0a8100bc41ee4eb0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-cb74ece9f4e1587d29fdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0159-0900000000-ea0ad48146cf3cb3f05eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-1900000000-7fcf7fa106c80ae63ecfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0159-0900000000-bcec7413699b72ce907fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-0726652dccc35c74fc75Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0910000000-8474d3a3c04960d1b93dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lr-0900000000-934e16bf5b31ef9ffe5fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000x-0970000000-e2028bd3c26899cfbf15Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0090000000-420ee0d5841c225f5a02Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-960a45368a4372744f2cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-fd04c8d24af5cc25c174Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-76c581aaed68618b0c30Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0159-1900000000-fabe8a6b7465a31024c4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0920000000-2b20de5e11254d5b1884Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-123b1555864cfc1ed243Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-5d4e5d3a54b7e1199497Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lr-0900000000-3fddeb3131c738943f36Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-1900000000-cb6cdf93db4207d114aaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0290000000-f40e79f27fd0f3448f9aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-2950000000-e144eddb8d64cdf24711Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0596-9500000000-9c44a89baee334f5ce9cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0090000000-f90eefcb5d4049067bbdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-2490000000-afd91ae0bad53e4c5c9fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02mi-6930000000-94751c5f94b6dd91d63eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0159-0920000000-433b403c3b42a7f8edeeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-f415ad05064e8739a03bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-9500000000-ceccb717da52c0d16783Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0090000000-e292d7944cba9edafe2eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001r-9230000000-e95b2e216923df5fefadNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-c2fa753da65a4bac80a1Not AvailableView Spectrum
Toxicity Profile
Toxicity Values
Toxicity ValueOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalToxicity RatingReference
546.0 Log mg/kg [310:970]RatLD50oralpredictedNot AvailableNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityBupropion selectively inhibits the neuronal reuptake of dopamine, norepinephrine, and serotonin; actions on dopaminergic systems are more significant than imipramine or amitriptyline whereas the blockade of norepinephrine and serotonin reuptake at the neuronal membrane is weaker for bupropion than for tricyclic antidepressants. The increase in norepinephrine may attenuate nicotine withdrawal symptoms and the increase in dopamine at neuronal sites may reduce nicotine cravings and the urge to smoke. Bupropion exhibits moderate anticholinergic effects.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsSymptoms of overdose include seizures, hallucinations, loss of consciousness, tachycardia, and cardiac arrest.
TreatmentEnsure an adequate airway, oxygenation, and ventilation. Monitor cardiac rhythm and vital signs. EEG monitoring is also recommended for the first 48 hours post-ingestion. General supportive and symptomatic measures are also recommended. Induction of emesis is not recommended. Activated charcoal should be administered. There is no experience with the use of forced diuresis, dialysis, hemoperfusion, or exchange transfusion in the management of bupropion overdoses. No specific antidotes for bupropion are known. Due to the dose-related risk of seizures with Bupropion, hospitalization following suspected overdose should be considered. Based on studies in animals, it is recommended that seizures be treated with intravenous benzodiazepine administration and other supportive measures, as appropriate. (12)
Health Effects
Health EffectRelationshipDirectionDescriptionReference
insomniaAssociated With?Not AvailableA disorder characterized by difficulty in falling asleep and/or remaining asleep. (NCI CTCAE)PMC8683172
abdominal obesity-metabolic syndromeNot AvailableNot AvailableNot AvailablePMC13299496
Weight lossNot AvailableNot AvailableNot AvailablePMC13399682
Weight lossHas Therapeutic Effect OnNot AvailableNot AvailablePMC12257286
XerostomiaAssociated With?Not AvailableNot AvailablePMC8683172
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
CEDs000051Surface water?Surface water can serve as a significant vector for the introduction of synthetic chemical contaminants into aquatic ecosystems.Aquatic systems & sedimentsPMC12424012 , PMC12424012
CEDs000070Stormwater runoff?Stormwater runoff refers to the flow of rainwater or melted snow that does not soak into the ground and instead collects pollutants as it travels over impervious surfaces such as roads and parking lots.Automotive & urban infrastructurePubChem
CEDs000260Antiobesity preparations, excl. diet products?Antiobesity preparations, excluding diet products, refer to pharmaceutical formulations designed to assist with weight management by altering metabolic processes, appetite regulation, or fat absorption.Healthcare, pharmaceuticals & veterinary productsNot Available
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
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
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
CEDs000555Bleaching Agents?Bleaching agents are chemical substances used to whiten or lighten materials, often employed in various cleaning products for their stain removal and disinfecting properties.Household cleaning & consumer productsPubChem
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
CEDs000562Pipe Accessories?Pipe accessories, such as fittings, connectors, and seals, are components used in plumbing systems to facilitate the flow of liquids and gases.Household cleaning & consumer productsPubChem
CEDs000563Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.Household cleaning & consumer productsPubChem
CEDs000566Tobacco Pipes?Tobacco pipes, often made from materials such as plastic, wood, or metal, can serve as sources of synthetic chemical contamination due to the residues left by tobacco products.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
CEDs000602Molluscicides?Molluscicides are synthetic chemicals specifically designed to control and eliminate mollusks, such as snails and slugs, which can be detrimental to crops and agricultural productivity.Agriculture & land managementPubChem
CEDs000603Nematocides?Nematocides are synthetic chemicals specifically designed to control nematodes, which are microscopic roundworms that can cause significant damage to crops and plants.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
CEDs000614Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.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
CEDs000634Buckles?Buckles, commonly used as fasteners in clothing, accessories, and furniture, can be a source of synthetic chemical contamination due to the materials and coatings employed in their production.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
CEDs000650Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.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
CEDs000678Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.Agriculture & land managementPubChem
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
CEDs000698Jewellery?Jewellery production often involves the use of various synthetic chemicals during the extraction and processing of metals.Mining & metal 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
CEDs000739Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.Paper, pulp & fiber productsPubChem
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
CEDs01154Human MilkFood, food processing & cookwarePMC11326520
CEDs02255WaterAquatic systems & sedimentsPMC12424012 , PMC10615923
CEDs02257WatersAquatic systems & sedimentsPMC10114359
CEDs02264SedimentAquatic systems & sedimentsPMC12424012
CEDs03028Wastewater EffluentWastewater, sanitation & biosolidsPMC12424012
Pathways
3 pathwaysPathway Source: PathBank
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cytochrome P450 2B6 structureClick to view 3D structureCytochrome P450 2B6P20813HumansKnownNot Available
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)
Prediction Confidence Score
0.409
Applicability Domain
1.0
Statistical Significance
0.005
Supporting Reference Compounds
506
E-value
39.0025
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)
Prediction Confidence Score
0.404
Applicability Domain
1.0
Statistical Significance
0.0048
Supporting Reference Compounds
451
E-value
37.6012
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)
Prediction Confidence Score
0.404
Applicability Domain
1.0
Statistical Significance
0.01
Supporting Reference Compounds
593
E-value
78.0049
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)
Prediction Confidence Score
0.4
Applicability Domain
1.0
Statistical Significance
0.0081
Supporting Reference Compounds
825
E-value
63.4471
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.376
Applicability Domain
1.0
Statistical Significance
0.0051
Supporting Reference Compounds
203
E-value
39.781
Neuronal acetylcholine receptor subunit alpha-7 structureClick to view 3D structureNeuronal acetylcholine receptor subunit alpha-7P36544HumansPredicted (SEA)
Prediction Confidence Score
0.359
Applicability Domain
1.0
Statistical Significance
0.0026
Supporting Reference Compounds
77
E-value
20.3965
Click to view 3D structurePeptidyl-prolyl cis-trans isomerase AP10111Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.313
Applicability Domain
0.313
Statistical Significance
0.0023
Supporting Reference Compounds
1
E-value
18.2167
Metabotropic glutamate receptor 5 structureClick to view 3D structureMetabotropic glutamate receptor 5P31424Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.312
Applicability Domain
0.38
Statistical Significance
0.0035
Supporting Reference Compounds
68
E-value
26.9358
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)
Prediction Confidence Score
0.297
Applicability Domain
0.38
Statistical Significance
0.0228
Supporting Reference Compounds
297
E-value
177.885
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)
Prediction Confidence Score
0.292
Applicability Domain
0.34
Statistical Significance
0.025
Supporting Reference Compounds
343
E-value
194.545
Vascular endothelial growth factor receptor 1 structureClick to view 3D structureVascular endothelial growth factor receptor 1P17948HumansPredicted (SEA)
Prediction Confidence Score
0.288
Applicability Domain
0.31
Statistical Significance
0.117
Supporting Reference Compounds
711
E-value
910.524
Click to view 3D structure15-cis-phytoene desaturaseP26294Synechococcus elongatus (strain PCC 7942) (Anacystis nidulans R2)Predicted (SEA)
Prediction Confidence Score
0.288
Applicability Domain
0.288 Low confidence
Statistical Significance
0.003
Supporting Reference Compounds
1
E-value
23.5883
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)
Prediction Confidence Score
0.285
Applicability Domain
0.313
Statistical Significance
0.0363
Supporting Reference Compounds
425
E-value
282.437
Metabotropic glutamate receptor 5 structureClick to view 3D structureMetabotropic glutamate receptor 5P41594HumansPredicted (SEA)
Prediction Confidence Score
0.285
Applicability Domain
0.333
Statistical Significance
0.0055
Supporting Reference Compounds
89
E-value
42.7392
Cathepsin B structureClick to view 3D structureCathepsin BP07858HumansPredicted (SEA)
Prediction Confidence Score
0.281
Applicability Domain
0.357
Statistical Significance
0.0384
Supporting Reference Compounds
173
E-value
299.019
O-phosphoserine sulfhydrylase structureClick to view 3D structureO-phosphoserine sulfhydrylaseP9WP53Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)
Prediction Confidence Score
0.28
Applicability Domain
0.28 Low confidence
Statistical Significance
0.0055
Supporting Reference Compounds
1
E-value
43.2063
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)
Prediction Confidence Score
0.28
Applicability Domain
0.38
Statistical Significance
0.0403
Supporting Reference Compounds
310
E-value
313.888
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)
Prediction Confidence Score
0.276
Applicability Domain
0.304
Statistical Significance
0.2274
Supporting Reference Compounds
1301
E-value
1770.68
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)
Prediction Confidence Score
0.275
Applicability Domain
0.286 Low confidence
Statistical Significance
0.2269
Supporting Reference Compounds
1157
E-value
1766.32
Click to view 3D structureTubulin alpha 4aC5ISA2Ovis ariesPredicted (SEA)
Prediction Confidence Score
0.275
Applicability Domain
0.275 Low confidence
Statistical Significance
0.002
Supporting Reference Compounds
1
E-value
15.2584
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)
Prediction Confidence Score
0.273
Applicability Domain
0.314
Statistical Significance
0.0419
Supporting Reference Compounds
192
E-value
326.5
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)
Prediction Confidence Score
0.271
Applicability Domain
0.308
Statistical Significance
0.3305
Supporting Reference Compounds
1498
E-value
2573.31
Beta-3 adrenergic receptor structureClick to view 3D structureBeta-3 adrenergic receptorP13945HumansPredicted (SEA)
Prediction Confidence Score
0.271
Applicability Domain
0.29 Low confidence
Statistical Significance
0.0162
Supporting Reference Compounds
145
E-value
126.116
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)
Prediction Confidence Score
0.271
Applicability Domain
0.313
Statistical Significance
0.1532
Supporting Reference Compounds
553
E-value
1192.96
Beta-1 adrenergic receptor structureClick to view 3D structureBeta-1 adrenergic receptorP08588HumansPredicted (SEA)
Prediction Confidence Score
0.27
Applicability Domain
0.29 Low confidence
Statistical Significance
0.0282
Supporting Reference Compounds
180
E-value
219.691
Broad substrate specificity ATP-binding cassette transporter ABCG2 structureClick to view 3D structureBroad substrate specificity ATP-binding cassette transporter ABCG2Q9UNQ0HumansKnownNot Available
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansKnownBupropion selectively inhibits the neuronal reuptake of dopamine, norepinephrine, and serotonin; actions on dopaminergic systems are more significant than imipramine or amitriptyline whereas the blockade of norepinephrine and serotonin reuptake at the neuronal membrane is weaker for bupropion than for tricyclic antidepressants. The increase in norepinephrine may attenuate nicotine withdrawal symptoms and the increase in dopamine at neuronal sites may reduce nicotine cravings and the urge to smoke. Bupropion exhibits moderate anticholinergic effects.
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansKnownBupropion selectively inhibits the neuronal reuptake of dopamine, norepinephrine, and serotonin; actions on dopaminergic systems are more significant than imipramine or amitriptyline whereas the blockade of norepinephrine and serotonin reuptake at the neuronal membrane is weaker for bupropion than for tricyclic antidepressants. The increase in norepinephrine may attenuate nicotine withdrawal symptoms and the increase in dopamine at neuronal sites may reduce nicotine cravings and the urge to smoke. Bupropion exhibits moderate anticholinergic effects.
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansKnownNot Available
Neuronal acetylcholine receptor subunit alpha-3 structureClick to view 3D structureNeuronal acetylcholine receptor subunit alpha-3P32297HumansKnownNot Available
Neuronal acetylcholine receptor subunit alpha-4 structureClick to view 3D structureNeuronal acetylcholine receptor subunit alpha-4P43681HumansKnownNot Available
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansKnownNot Available
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansKnownNot Available
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansKnownNot 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
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
Neuronal acetylcholine receptor subunit alpha-7 structureClick to view 3D structureNeuronal acetylcholine receptor subunit alpha-7P36544HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-3481
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBupropion
Chemspider ID431
ChEBI ID3219
PubChem Compound IDNot Available
Kegg Compound IDC06860
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

DrugSyn.org

MSDSLink
General References
  1. Thase ME, Clayton AH, Haight BR, Thompson AH, Modell JG, Johnston JA: A double-blind comparison between bupropion XL and venlafaxine XR: sexual functioning, antidepressant efficacy, and tolerability. J Clin Psychopharmacol. 2006 Oct;26(5):482-8. [PubMed: 16974189]
  2. Fryer JD, Lukas RJ: Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine. J Pharmacol Exp Ther. 1999 Jan;288(1):88-92. [PubMed: 9862757]
  3. Fava M, Rush AJ, Thase ME, Clayton A, Stahl SM, Pradko JF, Johnston JA: 15 years of clinical experience with bupropion HCl: from bupropion to bupropion SR to bupropion XL. Prim Care Companion J Clin Psychiatry. 2005;7(3):106-13. [PubMed: 16027765]
  4. Thase ME, Haight BR, Richard N, Rockett CB, Mitton M, Modell JG, VanMeter S, Harriett AE, Wang Y: Remission rates following antidepressant therapy with bupropion or selective serotonin reuptake inhibitors: a meta-analysis of original data from 7 randomized controlled trials. J Clin Psychiatry. 2005 Aug;66(8):974-81. [PubMed: 16086611]
  5. Annual report on the results of treatment in gynecological cancer. Twenty-first volume. Statements of results obtained in patients treated in 1982 to 1986, inclusive 3 and 5-year survival up to 1990. Int J Gynaecol Obstet. 1991 Sep;36 Suppl:1-315. [PubMed: 1684162]
  6. Mooney ME, Sofuoglu M: Bupropion for the treatment of nicotine withdrawal and craving. Expert Rev Neurother. 2006 Jul;6(7):965-81. [PubMed: 16831112]
  7. Hesse LM, Sakai Y, Vishnuvardhan D, Li AP, von Moltke LL, Greenblatt DJ: Effect of bupropion on CYP2B6 and CYP3A4 catalytic activity, immunoreactive protein and mRNA levels in primary human hepatocytes: comparison with rifampicin. J Pharm Pharmacol. 2003 Sep;55(9):1229-39. [PubMed: 14604466]
  8. Goodnick PJ: Pharmacokinetic optimisation of therapy with newer antidepressants. Clin Pharmacokinet. 1994 Oct;27(4):307-30. [PubMed: 7834966]
  9. Inoue T, Kitaichi Y, Koyama T: [Treatment strategy of refractory depression and its presynaptic mechanism of action]. Nihon Shinkei Seishin Yakurigaku Zasshi. 2003 Feb;23(1):11-20. [PubMed: 12690637]
  10. Hu KQ, Tiyyagura L, Kanel G, Redeker AG: Acute hepatitis induced by bupropion. Dig Dis Sci. 2000 Sep;45(9):1872-3. [PubMed: 11052334]
  11. Drugs.com - http://www.drugs.com/cons/Bupropion.html
  12. RxList: The Internet Drug Index (2009). - http://www.rxlist.com/