{"ATC Code":["N - Nervous system","N06 - Psychoanaleptics","N06A - Antidepressants","N06AX - Other antidepressants","N06AX12","N06AX12","N06AX12 - Bupropion","QN - Nervous system","QN06 - Psychoanaleptics","QN06A - Antidepressants","QN06AX - Other antidepressants","QN06AX12 - Bupropion"],"Absorption, Distribution and Excretion":"Bupropion is currently available in 3 distinct, but bioequivalent formulations: immediate release (IR), sustained-release (SR), and extended-release (XL).   **Immediate Release Formulation** In humans, following oral administration of bupropion hydrochloride tablets, peak plasma bupropion concentrations are usually achieved within 2 hours. IR formulations provide a short duration of action and are therefore generally dosed three times per day.   **Sustained Release Formulation** In humans, following oral administration of bupropion hydrochloride sustained-release tablets (SR), peak plasma concentration (Cmax) of bupropion is usually achieved within 3 hours. SR formulations provide a 12-hour extended release of medication and are therefore generally dosed twice per day.   **Extended Release Formulation** Following single oral administration of bupropion hydrochloride extended-release tablets (XL) to healthy volunteers, the median time to peak plasma concentrations for bupropion was approximately 5 hours. The presence of food did not affect the peak concentration or area under the curve of bupropion. XL formulations provide a 24-hour extended release of medication and are therefore generally dosed once per day/   In a trial comparing chronic dosing with bupropion hydrochloride extended-release tablets (SR) 150 mg twice daily to bupropion immediate-release formulation 100 mg 3 times daily, the steady state Cmax for bupropion after bupropion hydrochloride sustained-release tablets (SR) administration was approximately 85% of those achieved after bupropion immediate-release formulation administration. Exposure (AUC) to bupropion was equivalent for both formulations. Bioequivalence was also demonstrated for all three major active metabolites (i.e., hydroxybupropion, threohydrobupropion and erythrohydrobupropion) for both Cmax and AUC. Thus, at steady state, bupropion hydrochloride sustained-release tablets (SR) given twice daily, and the immediate-release formulation of bupropion given 3 times daily, are essentially bioequivalent for both bupropion and the 3 quantitatively important metabolites.  Furthermore, in a study comparing 14-day dosing with bupropion hydrochloride extended-release tablets (XL), 300 mg once-daily to the immediate-release formulation of bupropion at 100 mg 3 times daily, equivalence was demonstrated for peak plasma concentration and area under the curve for bupropion and the three metabolites (hydroxybupropion, threohydrobupropion, and erythrohydrobupropion). Additionally, in a study comparing 14-day dosing with bupropion hydrochloride extended-release tablets (XL) 300 mg once daily to the sustained-release formulation of bupropion at 150 mg 2 times daily, equivalence was demonstrated for peak plasma concentration and area under the curve for bupropion and the three metabolites.  Bupropion hydrochloride extended-release tablets (SR) can be taken with or without food. Bupropion Cmax and AUC were increased by 11% to 35% and 16% to 19%, respectively, when bupropion hydrochloride extended-release tablets (SR) was administered with food to healthy volunteers in three trials. The food effect is not considered clinically significant.  Following a single-dose administration of bupropion hydrochloride extended-release tablets (SR) in humans, Cmax of bupropion's metabolite hydroxybupropion occurs approximately 6 hours post-dose and is approximately 10 times the peak level of the parent drug at steady state. The elimination half-life of hydroxybupropion is approximately 20 (±5) hours and its AUC at steady state is about 17 times that of bupropion. The times to peak concentrations for the erythrohydrobupropion and threohydrobupropion metabolites are similar to that of the hydroxybupropion metabolite. However, their elimination half-lives are longer, 33(±10) and 37 (±13) hours, respectively, and steady-state AUCs are 1.5 and 7 times that of bupropion, respectively.","Actives":["Hydroxybupropion","Threohydrobupropion","Erythrohydrobupropion"],"Adverse Effects":"Various adverse effects have been reported in patients receiving bupropion. Many of these side effects occur in more than 10% of patients.","Aliases":["Amfebutamone","Amfebutamon","amfebutamonum","Amfebutamona","Elontril","Bupropion slow release","bupropione","Bupropion extended release","α-(tert-butylamino)-m-chloropropiophenone","NSC-758686","1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone","CHEBI:3219","Dtxsid7022706","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)-","bupropionum","1-Propanone, 1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-","Zyban","Dtxcid002706","N06AX12","34841-39-9","Wellbutrin","Wellbatrin","Bupropion SR","CHEMBL894","Amfebutamonum","Bupropion (R)-Isomer","Brn 2101062","Unii-01zg3tpx31","Budeprion","Amfebutamone(Bupropion)","Spectrum_001663","SpecPlus_000954","(.+/-.)-Bupropion","2-(Tert-Butylamino)-3'-chloropropiophenone","Prestwick0_000249","Prestwick1_000249","Prestwick2_000249","Prestwick3_000249","Spectrum2_001659","Spectrum3_000644","Spectrum4_000614","Spectrum5_001406","Lopac0_000166","Schembl38777","BSPBio_000038","BSPBio_002247","KBioGR_001168","KBioSS_002143","Mls001424015","DivK1c_007050","SPBio_001817","SPBio_002257","BPBio1_000042","GTPL7135","Schembl29354885","HSDB 6988","KBio1_001994","KBio2_002143","KBio2_004711","KBio2_007279","KBio3_001467","GLXC-07760","HMS2051G10","HMS2089G14","HMS2232P04","HMS3369P11","HMS3393G10","1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]propan-1-one","AC-197","Bdbm50048392","EBC-26277","Mfcd00865373","STL373006","Akos015961770","CCG-100858","CCG-204261","DB01156","NC00108","NSC 758686","Sdccgsbi-0050154.p004","Mrf-0000143","Ncgc00015122-03","Ncgc00015122-04","Ncgc00015122-06","Ncgc00015122-07","Ncgc00015122-09","Ncgc00015122-14","Ncgc00015122-20","Ncgc00089751-02","Nci60_002714","Smr000472526","Sbi-0050154.p003","DB-048697","AB00053756","NS00000397","α-(tert-Butylamino)-m-chloropropiophenone","C06860","D07591","Propiophenone, 2-(tert-butylamino)-3'-chloro-","Ab00053756-16","Ab00053756-18","Ab00053756-19","Ab00053756_20","Ab00053756_21","En300-1707781","2-tert-Butylamino-1-(3-chlorophenyl)propan-1-one","L000725","2-(tert-butylamino)-3'-chloropropiophenone","(.+/-.)-2-(tert-Butylamino)-3'-chloropropiophenone","Brd-a05186015-003-05-7","Brd-a05186015-003-09-9","Brd-a05186015-003-19-8","Brd-a05186015-003-20-6","2-(tert-Butylamino)-1-(3-chlorophenyl)-1-propanone #","1-(3-Chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone","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)-, (.+/-.)-"],"Biological Half-Life":"24 hours","Boiling Point":"52 °C","CAS":"34911-55-2","Chemical Classes":"Pharmaceutical","ChemicalClasses":["cathinone"],"Chirality":"racemic","Classes":["Stimulant"],"Color/Form":"Pale yellow oil","DBI-IGS":["Bupropion"],"Dosing Info":[{"Method":"Intravenous","Tiers":{"Common":{"Entries":4,"Lower":43.1,"Percentage":40,"Unit":"mg","Upper":50},"Extreme":{"Entries":2,"Lower":74.4,"Percentage":20,"Unit":"mg","Upper":74.4},"Heavy":{"Entries":1,"Lower":57.5,"Percentage":10,"Unit":"mg","Upper":74.4},"Light":{"Entries":3,"Lower":43.1,"Percentage":30,"Unit":"mg","Upper":43.1},"Strong":{"Entries":0,"Lower":50,"Percentage":0,"Unit":"mg","Upper":57.5}}},{"Method":"Oral","Tiers":{"Common":{"Entries":136,"Lower":200,"Percentage":58.9,"Unit":"mg","Upper":300},"Extreme":{"Entries":1,"Lower":300,"Percentage":0.4,"Unit":"mg","Upper":300},"Heavy":{"Entries":0,"Lower":300,"Percentage":0,"Unit":"mg","Upper":300},"Light":{"Entries":94,"Lower":200,"Percentage":40.7,"Unit":"mg","Upper":200},"Strong":{"Entries":0,"Lower":300,"Percentage":0,"Unit":"mg","Upper":300}}}],"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.","DurationOfAction":"","EliminationHalfLife":"Bupropion: alpha: 0.5 – 1.04beta: 11 hHydroxybupropion: 20 hThreohydrobupropion: 37 hErythrohydrobupropion: 33 h","Erowid Experience Reports":[{"Author":"Nat","Id":98113,"Title":"Won't Be Doing This Again"},{"Author":"Whitney","Id":82309,"Title":"Not Worth It at All"},{"Author":"deus ex machina 470","Id":28129,"Title":"No Noticeable Results"},{"Author":"2ton","Id":30057,"Title":"Smoking Failure"},{"Author":"Misplaced Fate1313","Id":36541,"Title":"Weak Sleep Patterns"},{"Author":"fastlane420","Id":99525,"Title":"Six Months Solid and No Real Side Effects"},{"Author":"Pointless","Id":21704,"Title":"Floatiness and Vivid Imagination"},{"Author":"WhiteRook","Id":99595,"Title":"Dangers With Insufflation"},{"Author":"Batman","Id":20042,"Title":"Increased Awareness"},{"Author":"Agency","Id":68287,"Title":"No Buzz, No Hangover, Just a Perfect World"},{"Author":"rookie4life","Id":72396,"Title":"Who Would Have Thought It Could Be Fun?!"},{"Author":"Daytripper","Id":27141,"Title":"Definetly Uplifting"},{"Author":"Cartbox","Id":41176,"Title":"Euphoric Withdrawals?"},{"Author":"starfire_xes","Id":76370,"Title":"A Novel Antitdepressant/Stimulant"},{"Author":"Blm22","Id":76560,"Title":"Nothing Much-Slight Euphoria"},{"Author":"depressed_guy","Id":91047,"Title":"Ugh..."},{"Author":"witty","Id":35088,"Title":"Vibration Noise"},{"Author":"Skip","Id":38007,"Title":"Medication-Inhibited Trip"},{"Author":"Samantha","Id":67925,"Title":"Nothing Special"},{"Author":"Old Hippy","Id":105027,"Title":"Disabled Vet Seeking Answers"},{"Author":"Rapkarla","Id":54624,"Title":"Disappointment"},{"Author":"Travisbickle","Id":52907,"Title":"Feeling like Johnny Cash at His Worst"},{"Author":"Zooey Glass","Id":6908,"Title":"Experimenting with Wellbutrin"},{"Author":"Zero Sum","Id":32204,"Title":"Depression + Studying"},{"Author":"drugstore cowboy","Id":9266,"Title":"Snorting Wellbutrin"},{"Author":"Kate","Id":57745,"Title":"Is This a Seizure?"}],"Esters":[],"FDA Pharmacological Classification":[{"Name":"FDA UNII","ReferenceNumber":28,"Value":{"StringWithMarkup":[{"String":"01ZG3TPX31"}]}},{"Name":"Active Moiety","ReferenceNumber":28,"Value":{"StringWithMarkup":[{"String":"BUPROPION"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":28,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-1176","Length":11,"Start":40,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Aminoketone"}],"String":"Established Pharmacologic Class [EPC] - Aminoketone"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":28,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-681","Length":8,"Start":29,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Dopamine"}],"String":"Mechanisms of Action [MoA] - Dopamine Uptake Inhibitors"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":28,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-681","Length":8,"Start":37,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Dopamine"}],"String":"Physiologic Effects [PE] - Increased Dopamine Activity"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":28,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5814","Length":14,"Start":37,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Norepinephrine"}],"String":"Physiologic Effects [PE] - Increased Norepinephrine Activity"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":28,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5814","Length":14,"Start":29,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Norepinephrine"}],"String":"Mechanisms of Action [MoA] - Norepinephrine Uptake Inhibitors"}]}},{"Name":"FDA Pharmacology Summary","ReferenceNumber":28,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-444","Length":9,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Bupropion"},{"Extra":"CID-1176","Length":11,"Start":16,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Aminoketone"},{"Extra":"CID-444","Length":9,"Start":56,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/bupropion"},{"Extra":"CID-681","Length":8,"Start":74,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Dopamine"},{"Extra":"CID-5814","Length":14,"Start":105,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Norepinephrine"},{"Extra":"CID-444","Length":9,"Start":164,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/bupropion"},{"Extra":"CID-681","Length":8,"Start":199,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Dopamine"},{"Extra":"CID-5814","Length":14,"Start":232,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Norepinephrine"}],"String":"Bupropion is an Aminoketone. The mechanism of action of bupropion is as a Dopamine Uptake Inhibitor, and Norepinephrine Uptake Inhibitor. The physiologic effect of bupropion is by means of Increased Dopamine Activity, and Increased Norepinephrine Activity."}]}},{"Name":"Non-Proprietary Name","ReferenceNumber":98,"Value":{"StringWithMarkup":[{"String":"BUPROPION"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":98,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5814","Length":14,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Norepinephrine"},{"Extra":"CID-1176","Length":11,"Start":40,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Aminoketone"},{"Extra":"CID-681","Length":8,"Start":59,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Dopamine"},{"Extra":"CID-5814","Length":14,"Start":103,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Norepinephrine"},{"Extra":"CID-681","Length":8,"Start":143,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Dopamine"}],"String":"Norepinephrine Uptake Inhibitors [MoA]; Aminoketone [EPC]; Dopamine Uptake Inhibitors [MoA]; Increased Norepinephrine Activity [PE]; Increased Dopamine Activity [PE]"}]}}],"Formating":[],"HMDB ID":"HMDB0001510","HeavyAtomCount":16,"Human Drugs":"Antidepressants -\u003e Norepinephrine and dopamine reuptake inhibitors (NDRI)","Human Toxicity Values":"In two deaths attributed to bupropion, the doses in both cases were estimated ... to be less than 10 g.","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","Interactions":"Adverse neuropsychiatric events or reduced alcohol tolerance have been reported rarely in patients who ingested alcohol during bupropion therapy. Because of concerns that excessive use of alcohol or abrupt withdrawal from alcohol may be associated with an increased risk of seizures during bupropion therapy, patients receiving the drug should be advised to minimize or, if possible, avoid alcohol consumption.","KEGG Entries":[{"Id":"D00817","Interactions":[],"Synonyms":["Bupropion hydrochloride","Wellbutrin","Zyban"]},{"Id":"D07591","Interactions":[],"Synonyms":["Bupropion"]},{"Id":"D07938","Interactions":[],"Synonyms":["Bupropion hydrobromide","Aplenzin"]}],"MeSH Headers":[{"Id":"M0025361","Link":"https://id.nlm.nih.gov/mesh/M0025361.html","Name":"Bupropion","Ref":130},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":132},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":160},{"Id":"M000640785","Link":"https://id.nlm.nih.gov/mesh/M000640785.html","Name":"Smoking Cessation Agents","Ref":161},{"Id":"M0028000","Link":"https://id.nlm.nih.gov/mesh/M0028000.html","Name":"Antidepressive Agents, Second-Generation","Ref":162},{"Id":"M0028098","Link":"https://id.nlm.nih.gov/mesh/M0028098.html","Name":"Dopamine Uptake Inhibitors","Ref":163},{"Id":"M0590381","Link":"https://id.nlm.nih.gov/mesh/M0590381.html","Name":"Cytochrome P-450 CYP2D6 Inhibitors","Ref":164}],"MeSH Pharmacological Classification":[{"Id":"M000640785","Link":"https://id.nlm.nih.gov/mesh/M000640785.html","Name":"Smoking Cessation Agent","Ref":161},{"Id":"M0028000","Link":"https://id.nlm.nih.gov/mesh/M0028000.html","Name":"Antidepressive Agents, Second-Generation","Ref":162},{"Id":"M0028098","Link":"https://id.nlm.nih.gov/mesh/M0028098.html","Name":"Dopamine Uptake Inhibitor","Ref":163},{"Id":"M0590381","Link":"https://id.nlm.nih.gov/mesh/M0590381.html","Name":"Cytochrome P-450 CYP2D6 Inhibitor","Ref":164}],"Mechanism of Action":"Bupropion is a norepinephrine/dopamine-reuptake inhibitor (NDRI) that exerts its pharmacological effects by weakly inhibiting the enzymes involved in the uptake of the neurotransmitters norepinephrine and dopamine from the synaptic cleft, therefore prolonging their duration of action within the neuronal synapse and the downstream effects of these neurotransmitters. More specifically, bupropion binds to the norepinephrine transporter (NET) and the dopamine transporter (DAT).   Bupropion was originally classified as an \"atypical\" antidepressant because it does not exert the same effects as the classical antidepressants such as Monoamine Oxidase Inhibitors (MAOIs), Tricyclic Antidepressants (TCAs), or Selective Serotonin Reuptake Inhibitors (SSRIs). While it has comparable effectiveness to typical first-line options for the treatment of depression such as SSRIs, bupropion is a unique option for the treatment of MDD as it lacks any clinically relevant serotonergic effects, typical of other mood medications, or any effects on histamine or adrenaline receptors. Lack of activity at these receptors results in a more tolerable side effect profile; bupropion is less likely to cause sexual side effects, sedation, or weight gain as compared to SSRIs or TCAs, for example.  When used as an aid to smoking cessation, bupropion is thought to confer its anti-craving and anti-withdrawal effects by inhibiting dopamine reuptake, which is thought to be involved in the reward pathways associated with nicotine, and through the antagonism of the nicotinic acetylcholinergic receptor (AChR), thereby blunting the effects of nicotine. Furthermore, the stimulatory effects produced by bupropion in the central nervous system are similar to nicotine's effects, making low doses of bupropion a suitable option as a nicotine substitute.    When used in combination with [naltrexone] in the marketed product ContraveⓇ for chronic weight management, the two components are thought to have effects on areas of the brain involved in the regulation of food intake. This includes the hypothalamus, which is involved in appetite regulation, and the mesolimbic dopamine circuit, which is involved in reward pathways. Studies have shown that the combined activity of bupropion and [naltrexone] increase the firing rate of hypothalamic pro-opiomelanocortin (POMC) neurons and blockade of opioid receptor-mediated POMC auto-inhibition, which are associated with a reduction in food intake and increased energy expenditure. This combination was also found to reduce food intake when injected directly into the ventral tegmental area of the mesolimbic circuit in mice, which is an area associated with the regulation of reward pathways.","Melting Point":"233-234 °C","Metabolism/Metabolites":"Bupropion is extensively metabolized in humans. Three metabolites are active: hydroxybupropion, which is formed via hydroxylation of the tert-butyl group of bupropion, and the amino-alcohol isomers, threohydrobupropion and erythrohydrobupropion, which are formed via reduction of the carbonyl group. In vitro findings suggest that CYP2B6 is the principal isoenzyme involved in the formation of hydroxybupropion, while cytochrome P450 enzymes are not involved in the formation of threohydrobupropion. Hydroxybupropion has been shown to have the same affinity as bupropion for the norepinephrine transporter (NET) but approximately 50% of its antidepressant activity despite reaching concentrations of ~10-fold higher than that of the parent drug.  Oxidation of the bupropion side chain results in the formation of a glycine conjugate of meta-chlorobenzoic acid, which is then excreted as the major urinary metabolite. The potency and toxicity of the metabolites relative to bupropion have not been fully characterized. However, it has been demonstrated in an antidepressant screening test in mice that hydroxybupropion is one-half as potent as bupropion, while threohydrobupropion and erythrohydrobupropion are 5-fold less potent than bupropion. This may be of clinical importance because the plasma concentrations of the metabolites are as high as or higher than those of bupropion.  Bupropion and its metabolites exhibit linear kinetics following chronic administration of 300 to 450 mg per day.","MolecularFormula":"C\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eClNO","MolecularWeight":"239.74 g/mol","Non-Human Toxicity Values":"LD50 Mouse ip 230 mg/kg","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"],"Records":{"UNII":{"Impurities":[]}},"RefChem":"5624","RefCount":4,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Bupropion","Name":"Bupropion","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q834280","Name":"Bupropion","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB01156","Name":"Bupropion","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/444","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 May 11, 2026. \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 May 11, 2026. \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","TGA eBS – Product and Consumer Medicine Information Licence. 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class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"(R)-Bupropion"},{"ChemicalClasses":["cathinone"],"SMILES":"C[C@H](NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 111.992 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 0h112v50H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath fill=\"#000\" stroke=\"none\" d=\"M71.709 25.941h-.7l-1.75 15.24h4.2z\" class=\"bond\"/\u003e\u003cpath d=\"m71.359 25.941 10.045-5.799M87.71 20.142l10.045 5.799M97.755 25.941l-7.62 13.198M97.755 25.941l13.198 7.62M97.755 25.941l7.62-13.198M71.359 25.941l-13.198-7.62\" 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5.799M97.755 25.941l-7.62 13.198M97.755 25.941l13.198 7.62M97.755 25.941l7.62-13.198\" class=\"bond\"/\u003e\u003cpath fill=\"#ff0d0d\" stroke=\"none\" d=\"M60.42 3.078q0 .756-.256 1.328-.256.565-.756.881-.5.315-1.244.315-.757 0-1.263-.315-.506-.316-.756-.887-.244-.572-.244-1.334 0-.75.244-1.309.25-.566.756-.881T58.175.56q.733 0 1.233.316.5.309.756.875.256.565.256 1.327m-3.864 0q0 .923.387 1.459.393.53 1.221.53.839 0 1.22-.53.387-.536.387-1.459 0-.929-.387-1.452-.381-.524-1.209-.524-.833 0-1.226.524-.393.523-.393 1.452\" class=\"atom\"/\u003e\u003cpath fill=\"#1ff01f\" stroke=\"none\" d=\"M2.906 16.499q-.786 0-1.239.53-.452.524-.452 1.447 0 .91.417 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","Treatment":"Ensure 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. (L1712)","UNII":"01ZG3TPX31","Wikidata":"Q834280","Wikipedia":"Bupropion","XLogP":3.2}