1.0 2009-07-21 20:28:29 UTC 2026-05-14 16:58:18 UTC T3D2999 Bupropion SmallMolecule Bupropion is an exogenous organic compound with the formula C13H18ClNO and an average molecular weight of 239.74 g/mol. It exists as a solid at room temperature. Bupropion belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. It is used as an antidepressant and as an aid to smoking cessation treatment. The compound is detected in the liver and brain. Recorded exposure routes include oral administration and the occlusive dressing technique. Bupropion is a selective catecholamine reuptake inhibitor targeting norepinephrine and dopamine, with only a small effect on serotonin reuptake. It does not inhibit MAO. Its antidepressant effect is considered to be mediated by its dopaminergic and noradrenergic action. Specifically, it selectively inhibits the neuronal reuptake of dopamine, norepinephrine, and serotonin; however, its blockade of norepinephrine and serotonin reuptake at the neuronal membrane is weaker than that of tricyclic antidepressants, while its actions on dopaminergic systems are more significant than those of amitriptyline or imipramine. An increase in dopamine at neuronal sites may reduce the urge to smoke and nicotine cravings, while an increase in norepinephrine may attenuate nicotine withdrawal symptoms. The compound acts as a competitive alpha-3-beta-4-nicotinic antagonist, an action that correlates with the interruption of addiction. Its recorded protein targets include the sodium-dependent dopamine transporter (SLC6A3), sodium-dependent noradrenaline transporter (SLC6A2), sodium-dependent serotonin transporter (SLC6A4), and neuronal acetylcholine receptor subunits alpha-3 (CHRNA3), alpha-4 (CHRNA4), and alpha-7 (CHRNA7), among nine other proteins. It is found in antidepressants, antiobesity preparations, food preservation, and various consumer products including cigarettes and electrically stimulated smoking devices. Drug Food Toxin Synthetic Toxin Organic Compound Organochloride Amine Ester Drug Food Toxin Antidepressant Dopamine Uptake Inhibitor Antidepressant, Second-Generation Metabolite Synthetic Compound Antidepressive Agent, Second-Generation Human Neurotoxin (+-)-Bupropion Amfebutamona Amfebutamone Amfebutamonum Aplenzin Budeprion BUPROBAN Elontril Forfivo Prexaton Voxra Wellbatrin Wellbutrin Wellbutrin SR Wellbutrin XL Zyban C13H18ClNO 239.741 239.10769191 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one bupropion 34841-39-9 CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1 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 SNPPWIUOZRMYNY-UHFFFAOYSA-N Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Alkyl-phenylketones Alpha-amino ketones Aryl alkyl ketones Aryl chlorides Benzoyl derivatives Chlorobenzenes Dialkylamines Hydrocarbon derivatives Organic oxides Organochlorides Organopnictogen compounds Phenylpropanes Alkyl-phenylketone Alpha-aminoketone Amine Aromatic homomonocyclic compound Aryl alkyl ketone Aryl chloride Aryl halide Benzenoid Benzoyl Chlorobenzene Halobenzene Hydrocarbon derivative Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organochloride Organohalogen compound Organonitrogen compound Organopnictogen compound Phenylpropane Secondary aliphatic amine Secondary amine Aromatic homomonocyclic compounds aromatic ketone monochlorobenzenes propanone secondary amino compound Detected and Not Quantified Exogenous Membrane Brain Liver Bupropion Action Pathway SMP0125268 Bupropion Metabolism SMP0125320 Bupropion Drug Metabolism Action Pathway SMP0143576 Solid White powder. melting_point 233-234°C solubility 312 mg/ml logp 3.6 logp 3.28 ALOGPS logs -3.54 ALOGPS solubility 6.93e-02 g/l ALOGPS logp 3.27 ChemAxon pka_strongest_acidic 18.29 ChemAxon pka_strongest_basic 8.22 ChemAxon iupac 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one ChemAxon average_mass 239.741 ChemAxon mono_mass 239.10769191 ChemAxon smiles CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1 ChemAxon formula C13H18ClNO ChemAxon 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 ChemAxon inchikey SNPPWIUOZRMYNY-UHFFFAOYSA-N ChemAxon polar_surface_area 29.1 ChemAxon refractivity 67.7 ChemAxon polarizability 25.93 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon For sustained release, peak plasma concentrations are achieved within 3 hours. Bupropion selectively inhibits the neuronal reuptake of dopamine, norepinephrine, and serotonin; actions on dopaminergic systems are more significant than imipramine or amitriptyline whereas the blockade of norepinephrine and serotonin reuptake at the neuronal membrane is weaker for bupropion than for tricyclic antidepressants. The increase in norepinephrine may attenuate nicotine withdrawal symptoms and the increase in dopamine at neuronal sites may reduce nicotine cravings and the urge to smoke. Bupropion exhibits moderate anticholinergic effects. Reduction of the carbonyl groupand/or hydroxylation of the tert-butyl group of bupropion. Route of Elimination: Bupropion is extensively metabolized in humans. Oxidation of the bupropion side chain results in the formation of a glycine conjugate of metachlorobenzoic acid, which is then excreted as the major urinary metabolite. Following oral administration of 200 mg of 14C-bupropion in humans, 87% and 10% of the radioactive dose were recovered in the urine and feces, respectively. However, the fraction of the oral dose of bupropion excreted unchanged was only 0.5%, a finding consistent with the extensive metabolism of bupropion. Half Life: 24 hours No indication of carcinogenicity to humans (not listed by IARC). For the treatment of depression and as aid to smoking cessation. #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f721f757130> Symptoms of overdose include seizures, hallucinations, loss of consciousness, tachycardia, and cardiac arrest. 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) DB01156 HMDB01510 444 CHEMBL894 431 C06860 3219 CPD-3481 Bupropion Bupropion 16974189 9862757 16027765 16086611 1684162 16831112 14604466 7834966 12690637 11052334 Drugs.com: http://www.drugs.com/cons/Bupropion.html RxList: The Internet Drug Index (2009).: http://www.rxlist.com/ BE0000647 Bupropion selectively inhibits the neuronal reuptake of dopamine, norepinephrine, and serotonin; actions on dopaminergic systems are more significant than imipramine or amitriptyline whereas the blockade of norepinephrine and serotonin reuptake at the neuronal membrane is weaker for bupropion than for tricyclic antidepressants. The increase in norepinephrine may attenuate nicotine withdrawal symptoms and the increase in dopamine at neuronal sites may reduce nicotine cravings and the urge to smoke. Bupropion exhibits moderate anticholinergic effects. Inhibitory 0.441 uM BindingDB 50048392 Inhibitory 0.52 uM BindingDB 50048392 Inhibitory 0.562 uM BindingDB 50048392 Inhibitory 0.784 uM BindingDB 50048392 Inhibitory 0.871 uM BindingDB 50048392 IC50 0.658 uM BindingDB 50048392 IC50 0.66 uM BindingDB 50048392 IC50 0.945 uM BindingDB 50048392 IC50 1.567 uM BindingDB 50048392 IC50 2.9 uM BindingDB 50048392 BE0000486 Bupropion selectively inhibits the neuronal reuptake of dopamine, norepinephrine, and serotonin; actions on dopaminergic systems are more significant than imipramine or amitriptyline whereas the blockade of norepinephrine and serotonin reuptake at the neuronal membrane is weaker for bupropion than for tricyclic antidepressants. The increase in norepinephrine may attenuate nicotine withdrawal symptoms and the increase in dopamine at neuronal sites may reduce nicotine cravings and the urge to smoke. Bupropion exhibits moderate anticholinergic effects. Inhibitory 6.97 uM BindingDB 50048392 Inhibitory >10 uM BindingDB 50048392 IC50 0.443 uM BindingDB 50048392 IC50 1.45 uM BindingDB 50048392 IC50 1.85 uM BindingDB 50048392 BE0000749 Inhibitory 9.1 uM BindingDB 50048392 Inhibitory >10 uM BindingDB 50048392 IC50 47 uM BindingDB 50048392 IC50 >0.1 uM BindingDB 50048392 IC50 >100 uM BindingDB 50048392 BE0003585 IC50 1 uM BindingDB 50048392 IC50 1.8 uM BindingDB 50048392 BE0000849 IC50 0.012 uM BindingDB 50048392 IC50 12 uM BindingDB 50048392 BE0000560 Inhibitory >10 uM BindingDB 50048392 BE0000291 Inhibitory >10 uM BindingDB 50048392 BE0000533 Inhibitory >10 uM BindingDB 50048392 BE0000289 Inhibitory >10 uM BindingDB 50048392 BE0000442 Inhibitory >10 uM BindingDB 50048392 BE0000092 Inhibitory >10 uM BindingDB 50048392 BE0000045 Inhibitory >10 uM BindingDB 50048392 BE0000405 Inhibitory >10 uM BindingDB 50048392 BE0002341 IC50 50 uM BindingDB 50048392 BE0000311