File:Bupropion_structure.svg · Wikimedia Commons · See Wikimedia Commons
bupropion
Sign in to saveAlso known as amfebutamone, BW-323
Bupropion, formerly called amfebutamone, and sold under the brand name Wellbutrin among others, is an atypical antidepressant that is indicated in the treatment of major depressive disorder and seasonal affective disorder and to support smoking cessation. A norepinephrine–dopamine reuptake inhibitor (NDRI), it is also popular as an add-on medication in the cases of "incomplete response" to the first-line selective serotonin reuptake inhibitor (SSRI) antidepressant. Bupropion has several features that distinguish it from other antidepressants: It does not usually cause sexual dysfunction, it is
OverviewAI-generated
Bupropion is a chemical compound with the formula C₁₃H₁₈ClNO. Its IUPAC name is 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one. The substance has a mass of 239.107692 and a weight of 239.74. It is characterized by a defined daily dose of 0.3. The stylized name for the compound is buPROPion.
Chemical properties include an xlogp of 3.2 and a tpsa of 29.1. The molecule contains one hydrogen bond donor and two hydrogen bond acceptors, with a charge of 0. It is associated with a Commons category titled "Bupropion".
The compound is referenced by 3,580 other encyclopedia articles. A PubMed query for bupropion yields a count of 6368.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.index2_label
- as HCl
- Drug.CAS_number
- 34911-55-2
- Drug.Verifiedfields
- correct
- Drug.Watchedfields
- correct
- Drug.verifiedrevid
- 852547309
- Drug.image
- Racemic-Bupropion-2D-Skeletal.png
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.alt
- Skeletal formula of bupropion
- Drug.imageL
- (S)-Bupropion 3D-Ball-and-Stick Model generated with BIOVIA Discovery Visual Studio.png
- Drug.widthL
- 150
- Drug.imageR
- R-Isomer-Bupropion-3D-Ball-and-Stick.png
- Drug.widthR
- 150
- Drug.pronounce
- Bupropion: Amfebutamone:
- Drug.tradename
- Wellbutrin, Zyban, others
- Drug.MedlinePlus
- a695033
- Drug.DailyMedID
- Bupropion
- Drug.pregnancy_AU
- B2
via Wikipedia infobox
Chemical data
- Formula
- C13H18ClNO
- Molecular weight
- 239.74 g/mol
- IUPAC name
- 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
- SMILES
- CC(C(=O)C1=CC(=CC=C1)Cl)NC(C)(C)C
- InChIKey
- SNPPWIUOZRMYNY-UHFFFAOYSA-N
- XLogP
- 3.2
- Polar surface area
- 29.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
6,368 papers- Use of bupropion in combination with serotonin reuptake inhibitors.Biological psychiatry · 2006
- Pharmacokinetic and pharmacodynamic of bupropion: integrative overview of relevant clinical and forensic aspects.Drug metabolism reviews · 2019
- Bupropion and Anxiety: A Brief Review.Human psychopharmacology · 2025
- Bupropion-myth-busting!CNS spectrums · 2022
- Dextromethorphan/Bupropion: First Approval.CNS drugs · 2022
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 239.107692
- Image
- Bupropion.svg
- Has use
- medication
Show 12 more facts
- route of administration
- intravenous infusion and defusion
- chemical formula
- C₁₃H₁₈ClNO
- Commons category
- Bupropion
- World Health Organisation international non-proprietary name
- bupropion
- medical condition treated
- major depressive disorder
- canonical SMILES
- CC(C(=O)C1=CC(=CC=C1)Cl)NC(C)(C)C
- defined daily dose
- 0.3
- subject has role
- antidepressant
- different from
- buprenorphine
- significant drug interaction
- clomipramine
- stylized name
- buPROPion
- legal status (medicine)
- boxed warning
Sources (11)
via Wikidata · CC0
~39 min read
Encyclopedic overview
27 sectionsContents
- Medical uses
- Depression
- Smoking cessation
- Attention deficit hyperactivity disorder
- Sexual dysfunction
- Weight loss
- Other uses
- Available forms
- Contraindications
- Side effects
- Psychiatric
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Synthesis
- Analogues
- History
- Society and culture
- Recreational use
- Legal status
- Brand names
- Research
- See also
- References
Bupropion, formerly called amfebutamone, and sold under the brand name Wellbutrin among others, is an atypical antidepressant that is indicated in the treatment of major depressive disorder and seasonal affective disorder and to support smoking cessation. A norepinephrine–dopamine reuptake inhibitor (NDRI), it is also popular as an add-on medication in the cases of "incomplete response" to the first-line selective serotonin reuptake inhibitor (SSRI) antidepressant. Bupropion has several features that distinguish it from other antidepressants: It does not usually cause sexual dysfunction, it is not associated with weight gain or sleepiness, and it is more effective than SSRIs at improving symptoms of hypersomnia and fatigue. Bupropion, particularly the immediate-release formulation, carries a higher risk of seizure than many other antidepressants; hence, caution is recommended in patients with a history of seizure disorder. The medication is taken by mouth.
Common adverse effects of bupropion with the greatest difference from placebo are dry mouth, nausea, constipation, insomnia, anxiety, tremor, and excessive sweating. Raised blood pressure is notable. Rare but serious side effects include seizures, liver toxicity, psychosis, and risk of overdose. Bupropion use during pregnancy may be associated with increased likelihood of congenital heart defects.
Excerpted from Wikipedia’s “bupropion” article, available under the CC BY-SA 4.0 licence.