CHEBI:3219 - bupropion

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ChEBI Name bupropion
ChEBI ID CHEBI:3219
Definition An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C13H18ClNO
Net Charge 0
Average Mass 239.74086
Monoisotopic Mass 239.108
InChI 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
InChIKey SNPPWIUOZRMYNY-UHFFFAOYSA-N
SMILES CC(NC(C)(C)C)C(=O)c1cccc(Cl)c1
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
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ChEBI Ontology
Outgoing bupropion (CHEBI:3219) has role antidepressant (CHEBI:35469)
bupropion (CHEBI:3219) has role environmental contaminant (CHEBI:78298)
bupropion (CHEBI:3219) has role xenobiotic (CHEBI:35703)
bupropion (CHEBI:3219) is a aromatic ketone (CHEBI:76224)
bupropion (CHEBI:3219) is a monochlorobenzenes (CHEBI:83403)
bupropion (CHEBI:3219) is a secondary amino compound (CHEBI:50995)
Incoming (R)-bupropion (CHEBI:36794) is a bupropion (CHEBI:3219)
(S)-bupropion (CHEBI:36793) is a bupropion (CHEBI:3219)
IUPAC Name
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
Synonym Source
Bupropion KEGG COMPOUND
Manual Xrefs Databases
435 DrugCentral
Bupropion Wikipedia
C06860 KEGG COMPOUND
CPD-3481 MetaCyc
D07591 KEGG DRUG
DB01156 DrugBank
HMDB0001510 HMDB
LSM-1267 LINCS
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Registry Numbers Types Sources
2101062 Beilstein Registry Number ChemIDplus
2101062 Reaxys Registry Number Reaxys
34841-39-9 CAS Registry Number KEGG COMPOUND
34911-55-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12826985 PubMed citation Europe PMC
15876900 PubMed citation Europe PMC
Last Modified
06 February 2018
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag