{"ATC Code":"N06AX12","Abbreviation":"","Actives":["Hydroxybupropion","Threohydrobupropion","Erythrohydrobupropion"],"Aliases":["Amfebutamone","Amfebutamon","amfebutamonum","Amfebutamona","Elontril","Bupropion slow release","bupropione","Bupropion extended release","α-(tert-butylamino)-m-chloropropiophenone","1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone","2-(tert-Butylamino)-3'-chlorpropiophenon","2-(tert-Butylamino)-3'-chloropropiophenone","1-Propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-","1-Propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-, (+-)-","1-Propanone, 1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-","Zyban","bupropionum","N06AX12","Wellbutrin","34841-39-9","Wellbatrin","Bupropion SR","1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]propan-1-one","Bupropion (R)-Isomer","Budeprion"],"Biological Half-Life":"24 hours","Boiling Point":"52 °C","CAS":"34911-55-2","ChEBI":"CHEBI:3219","ChEMBL":"CHEMBL894","ChemicalClasses":["cathinone"],"Chirality":"racemic","Classes":["Stimulant"],"Color/Form":"Pale yellow oil","Drug Classes":"Breast Feeding; Lactation; Milk, Human; Antidepressive Agents; Antidepressive Agents, Second-Generation; Dopamine Uptake Inhibitors; Smoking Cessation Agents","Drug Indication":"Bupropion is indicated for the treatment of major depressive disorder (MDD), seasonal affective disorder (SAD), and as an aid to smoking cessation.   When used in combination with [naltrexone] as the marketed product ContraveⓇ, bupropion is indicated as an adjunct to a reduced-calorie diet and increased physical activity for chronic weight management in adults with an initial body mass index (BMI) of: 30 kg/m^2 or greater (obese) or 27 kg/m^2 or greater (overweight) in the presence of at least one weight-related comorbid condition (e.g., hypertension, type 2 diabetes mellitus, or dyslipidemia).  Bupropion is also used off-label as a first-line treatment in patients with ADHD and comorbid bipolar disorder when used as an adjunct to mood stabilizers.","Drug Warnings":"/BOXED WARNING/ WARNING: NEUROPSYCHIATRIC REACTIONS IN PATIENTS TAKING BUPROPION FOR SMOKING CESSATION. Serious neuropsychiatric reactions have occurred in patients taking Zyban for smoking cessation. The majority of these reactions occurred during bupropion treatment, but some occurred in the context of discontinuing treatment. In many cases, a causal relationship to bupropion treatment is not certain, because depressed mood may be a symptom of nicotine withdrawal. However, some of these symptoms have occurred in patients taking Zyban who continued to smoke. The risks of Zyban should be weighed against the benefits of its use. Zyban has been demonstrated to increase the likelihood of abstinence from smoking for as long as 6 months compared with treatment with placebo. The health benefits of quitting smoking are immediate and substantial.","Erowid Experience Reports":null,"Esters":[],"FDA Pharmacological Classification":"01ZG3TPX31","Formating":[],"HMDB ID":"HMDB0001510","HeavyAtomCount":16,"Human Drugs":"Antidepressants -\u003e Norepinephrine and dopamine reuptake inhibitors (NDRI)","IUPACName":"2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one","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","MeSH Pharmacological Classification":"Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2D6. (See all compounds classified as Cytochrome P-450 CYP2D6 Inhibitors.)","Melting Point":"233-234 °C","MolecularFormula":"C\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eClNO","MolecularWeight":"239.74 g/mol","Opticalactivity":"( + / - )","Pharmacodynamics":"Bupropion is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitors, or other known antidepressant agents. Compared to classical tricyclic antidepressants, Bupropion is a relatively weak inhibitor of the neuronal uptake of norepinephrine and dopamine. In addition, Bupropion does not inhibit monoamine oxidase. Bupropion has been found to be essentially inactive at the serotonin transporter (SERT)(IC50 \u003e10 000 nM), however both bupropion and its primary metabolite hydroxybupropion have been found to block the function of cation-selective serotonin type 3A receptors (5-HT3ARs).   Bupropion produces dose-related central nervous system (CNS) stimulant effects in animals, as evidenced by increased locomotor activity, increased rates of responding in various schedule-controlled operant behaviour tasks, and, at high doses, induction of mild stereotyped behaviour. Due to these stimulant effects and selective activity at dopamine and norepinephrine receptors, bupropion has been identified as having an abuse potential. Bupropion has a similar structure to the controlled substance [DB01560], and has been identified as having mild amphetamine-like activity, particularly when inhaled or injected.  Bupropion is also known to lower the seizure threshold, making any pre-existing seizure conditions a contraindication to its use. This risk is exacerbated when bupropion is combined with other drugs or substances that lower the seizure threshold, such as [cocaine], or in clinical situations that would increase the risk of a seizure such as abrupt alcohol or benzodiazepine withdrawal. As norepinephrine has been shown to have anticonvulsant properties, bupropion's inhibitory effects on NET are thought to contribute to its pro-convulsant activity.  Bupropion has been shown to increase blood pressure and pose a risk for exacerbation of unmanaged or pre-existing hypertension, however, clinical trials of bupropion in smokers with CVD have not identified an increased incidence of CV events including stroke or heart attack. In clinical trials, the mean increase in systolic blood pressure associated with the use of bupropion was found to be 1.3 mmHg.","Physical Description":"Solid","PubChemId":444,"Record Description":["LiverTox|CNS|Antidepressant|Aminoketone"],"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Bupropion","Name":"Bupropion","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB01156","Name":"Bupropion","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/444","Name":"Bupropion","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL894","Name":"Bupropion","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3219","Name":"Bupropion","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=34911-55-2","Name":"Bupropion","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0001510","Name":"Bupropion","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C06860","Name":"Bupropion","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/01ZG3TPX31","Name":"Bupropion","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID7022706","Name":"Bupropion","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 444, Bupropion. Accessed July 19, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/444\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/444\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Bupropion. UNII: 01ZG3TPX31. Global Substance Registration System. Accessed July 19, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/01ZG3TPX31\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/01ZG3TPX31\u003c/a\u003e"],"Reported Fatal Dose":"In two deaths attributed to bupropion, the doses in both cases were estimated ... to be less than 10 g.","SMILES":"CC(C(=O)C1=CC(=CC=C1)Cl)NC(C)(C)C","SaltData":[{"AcidCount":1,"AmineCount":1,"Formula":"Br","Name":"hydrobromide","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 136.315 49.848\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h137v50H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"M71.359 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decomposition","Stability/Shelf Life":"Stable under recommended storage conditions.","StereoisomerData":[{"Aliases":null,"PubChemId":null,"SMILES":"C[C@@H](NC(C)(C)C)C(=O)c1cccc(Cl)c1","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 94.469 67.128\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h95v68H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M54.186 25.941h-.7M54.436 28.118h-1.2M54.686 30.295h-1.7M54.936 32.473h-2.2M55.186 34.65h-2.7M55.436 36.827h-3.2M55.686 39.004h-3.7M55.936 41.181h-4.2\"/\u003e\u003c/g\u003e\u003cpath d=\"m53.836 25.941 10.045-5.799M70.187 20.142l10.045 5.799M80.232 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1.446.422.53 1.268.53.321 0 .607-.054.291-.059.565-.142v.535q-.274.102-.565.149-.292.054-.697.054-.744 0-1.25-.31-.5-.309-.75-.875-.25-.571-.25-1.339 0-.745.268-1.31.274-.566.804-.881.529-.322 1.279-.322.78 0 1.352.286l-.244.524q-.226-.101-.506-.185-.274-.083-.607-.083m2.756 4.423h-.601v-5.215h.601z\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M86.498 20.771h-.721l-2.619-4.066h-.03l.03.595q.024.357.024.732v2.739h-.566v-4.9h.715l2.607 4.055h.03l-.018-.328-.024-.476q-.006-.262-.006-.482v-2.769h.578zM86.361 15.31h-.619v-2.286h-2.513v2.286h-.613v-4.9h.613v2.072h2.513V10.41h.619z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#1ff01f\" d=\"m6.875 19.188 5.843 3.372\" class=\"hi\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m81.404 20.142-5.023 2.899M81.404 20.142l-5.023 2.899M87.71 20.142l5.022 2.899M87.71 20.142l5.022 2.899\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Subjective Effects":{"Cognitive Effects":["Analysis enhancement","Ego inflation","Focus enhancement","Increased music appreciation","Motivation enhancement","Thought acceleration","Wakefulness","Disinhibition","Suggestibility suppression","Cognitive euphoria","Compulsive redosing","Mania"],"Physical Effects":["Increased libido","Stamina enhancement","Stimulation","Appetite suppression","Dehydration","Dry mouth","Restless legs","Shakiness","Teeth grinding","Abnormal heartbeat","Increased blood pressure","Increased heart rate","Vasoconstriction"],"Visual Effects":[]},"Therapeutic Uses":"Antidepressive Agents, Second-Generation; Dopamine Uptake Inhibitors","Title":"Bupropion","UNII":"01ZG3TPX31","Wikipedia":"Bupropion","XLogP":3.2}