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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:00:08 UTC
HMDB IDHMDB0001510
Secondary Accession Numbers
  • HMDB01510
Metabolite Identification
Common NameBupropion
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.
Structure
Data?1582752206
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 Weight239.741
Monoisotopic Molecular Weight239.10769191
IUPAC Name2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
Traditional Namebupropion
CAS Registry Number34841-39-9
SMILES
CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M+H]+CBM157.830932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.069 g/LALOGPS
logP10(3.28) g/LALOGPS
logP10(3.27) g/LChemAxon
logS10(-3.5) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+31661259
DarkChem[M-H]-31661259
AllCCS[M+H]+152.15532859911
AllCCS[M-H]-156.94732859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bupropion GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-5900000000-1b5fb2e947791614a61d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bupropion GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bupropion GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-qTof , Positive-QTOFsplash10-001i-0910000000-fa2592b7296c7561333c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-c10af1c8e3619fe0bffc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-0006-0490000000-55448af4d9a8ce866a882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-2883ba18321a8b8228a12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-0159-0900000000-7d6cad849706146ddab32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-0159-0900000000-0fca8999746b69ee4fc12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-b64f8d2b50bede574f632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-2edefa63d5f6f1b08db72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-0006-0490000000-b8ea1de058a84547700d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-001i-0910000000-6f471b9150fb1b7f6fcc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-0159-0900000000-cc966137ee3283828af72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-00lr-0900000000-7f86f38f740aa41b244b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-e7f2cfdbabbd35a9b6432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-4daf0e10db1e5f2750bf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-f77a450be176593153d22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion , positive-QTOFsplash10-00m0-0910000000-d2eb7265b058766459c92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion , positive-QTOFsplash10-001i-0910000000-fa2592b7296c7561333c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion LC-ESI-QFT , positive-QTOFsplash10-001i-0900000000-4d831e97d7e7dfff141b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bupropion 60V, Positive-QTOFsplash10-00lr-0900000000-65c6a707c92719eb037b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupropion 10V, Positive-QTOFsplash10-0006-0290000000-f40e79f27fd0f3448f9a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupropion 20V, Positive-QTOFsplash10-000x-2950000000-e144eddb8d64cdf247112016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupropion 40V, Positive-QTOFsplash10-0596-9500000000-9c44a89baee334f5ce9c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupropion 10V, Negative-QTOFsplash10-000i-0090000000-f90eefcb5d4049067bbd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupropion 20V, Negative-QTOFsplash10-000i-2490000000-afd91ae0bad53e4c5c9f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bupropion 40V, Negative-QTOFsplash10-02mi-6930000000-94751c5f94b6dd91d63e2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Brain
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID431
KEGG Compound IDC06860
BioCyc IDCPD-3481
BiGG IDNot Available
Wikipedia LinkBupropion
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID3219
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceXia, Min; Xu, Bao-feng. Study on synthesis of the amfebutamone hydrochloride. Shandong Huagong (2003), 32(3), 3-5.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mooney ME, Sofuoglu M: Bupropion for the treatment of nicotine withdrawal and craving. Expert Rev Neurother. 2006 Jul;6(7):965-81. [PubMed:16831112 ]
  2. 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 ]
  3. Goodnick PJ: Pharmacokinetic optimisation of therapy with newer antidepressants. Clin Pharmacokinet. 1994 Oct;27(4):307-30. [PubMed:7834966 ]
  4. 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 ]
  5. Hu KQ, Tiyyagura L, Kanel G, Redeker AG: Acute hepatitis induced by bupropion. Dig Dis Sci. 2000 Sep;45(9):1872-3. [PubMed:11052334 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular weight:
68494.255

Transporters

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular weight:
69331.42