Bupropion (CHEM002358)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:29 UTC
Update Date2026-03-26 18:30:19 UTC
Accession NumberCHEM002358
Identification
Common NameBupropion
ClassSmall Molecule
DescriptionBupropion is a selective catecholamine (norepinephrine and dopamine) reuptake inhibitor. It has only a small effect on serotonin reuptake. It does not inhibit MAO. The antidepressant effect of bupropion is considered to be mediated by its dopaminergic and noradrenergic action. Bupropion has also been shown to act as a competitive alpha-3-beta-4- nicotinic antagonist, the alpha-3-beta-4-antagonism has been shown to interrupt addiction in studies of other drugs such as ibogaine. This alpha-3-beta-4-antagonism correlates quite well with the observed effect of interrupting addiction. A unicyclic, aminoketone antidepressant. The mechanism of its therapeutic actions is not well understood, but it does appear to block dopamine uptake. The hydrochloride is available as an aid to smoking cessation treatment; Bupropion is a selective catecholamine (norepinephrine and dopamine) reuptake inhibitor. It has only a small effect on serotonin reuptake. It does not inhibit MAO. The antidepressant effect of bupropion is considered to be mediated by its dopaminergic and noradrenergic action. Bupropion has also been shown to act as a competitive alpha-3-beta-4-nicotinic antagonist, the alpha-3-beta-4-antagonism has been shown to interrupt addiction in studies of other drugs such as ibogaine. This alpha-3-beta-4-antagonism correlates quite well with the observed effect of interrupting addiction. Bupropion (amfebutamone) (brand names Wellbutrin and Zyban) is an antidepressant of the aminoketone class, chemically unrelated to tricyclics or selective serotonin reuptake inhibitors (SSRIs). It is similar in structure to the stimulant cathinone, and to phenethylamines in general. It is a chemical derivative of diethylpropion, an amphetamine-like substance used as an anorectic. Bupropion is both a dopamine reuptake inhibitor and a norepinephrine reuptake inhibitor. It is often used as a smoking cessation aid.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds - Waste Water
  • T3DB toxins
Contaminant Type
  • Amine
  • Antidepressant
  • Antidepressant, Second-Generation
  • Antidepressive Agent, Second-Generation
  • Dopamine Uptake Inhibitor
  • Drug
  • Ester
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-5900000000-1b5fb2e947791614a61dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-0910000000-fa2592b7296c7561333cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-c10af1c8e3619fe0bffcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0490000000-55448af4d9a8ce866a88Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-2883ba18321a8b8228a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0159-0900000000-7d6cad849706146ddab3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0159-0900000000-0fca8999746b69ee4fc1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-b64f8d2b50bede574f63Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-2edefa63d5f6f1b08db7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0490000000-b8ea1de058a84547700dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0910000000-6f471b9150fb1b7f6fccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0159-0900000000-cc966137ee3283828af7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00lr-0900000000-7f86f38f740aa41b244bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-e7f2cfdbabbd35a9b643Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-4daf0e10db1e5f2750bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-f77a450be176593153d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00m0-0910000000-d2eb7265b058766459c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0910000000-fa2592b7296c7561333cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0900000000-4d831e97d7e7dfff141bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00lr-0900000000-65c6a707c92719eb037bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0290000000-f40e79f27fd0f3448f9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-2950000000-e144eddb8d64cdf24711Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9500000000-9c44a89baee334f5ce9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-f90eefcb5d4049067bbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2490000000-afd91ae0bad53e4c5c9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02mi-6930000000-94751c5f94b6dd91d63eSpectrum
Toxicity Profile
Route of ExposureFor sustained release, peak plasma concentrations are achieved within 3 hours.
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.
MetabolismReduction of the carbonyl groupand/or hydroxylation of the tert-butyl group of bupropion. Route of Elimination: Bupropion is extensively metabolized in humans. Oxidation of the bupropion side chain results in the formation of a glycine conjugate of metachlorobenzoic acid, which is then excreted as the major urinary metabolite. Following oral administration of 200 mg of 14C-bupropion in humans, 87% and 10% of the radioactive dose were recovered in the urine and feces, respectively. However, the fraction of the oral dose of bupropion excreted unchanged was only 0.5%, a finding consistent with the extensive metabolism of bupropion. Half Life: 24 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of depression and as aid to smoking cessation.
Minimum Risk LevelNot Available
Health EffectsNot 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)
Concentrations
Not Available
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. https://www.ncbi.nlm.nih.gov/pubmed/?term=12826985
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15876900