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bupropion hydrochloride
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride (1:1)

Supplier Sponsors

CAS Number: 31677-93-7Picture of molecule3D/inchi
Other(deleted CASRN):34841-36-6
ECHA EINECS - REACH Pre-Reg:250-759-9
FDA UNII: ZG7E5POY8O
MDL:MFCD00055209
Molecular Weight:276.20463000
Formula:C13 H19 Cl2 N O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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US Patents:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:white crystalline powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 233.00 °C. @ 760.00 mm Hg (est)
Boiling Point: 334.80 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.000125 mmHg @ 25.00 °C. (est)
Flash Point: 313.00 °F. TCC ( 156.30 °C. ) (est)
logP (o/w): 3.468 (est)
Soluble in:
 water, 3849 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
American International Chemical, LLC.
Bupropion HCI
BOC Sciences
For experimental / research use only.
Bupropion HCl >98%
Santa Cruz Biotechnology
For experimental / research use only.
Bupropion HCl
Sigma-Aldrich: Sigma
For experimental / research use only.
Bupropion hydrochloride ≥98% (HPLC), solid
sds
TCI AMERICA
For experimental / research use only.
Bupropion Hydrochloride >98.0%(HPLC)(T)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-man LDLo 329 mg/kg
CARDIAC: PULSE RATE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: OTHER CHANGES
Journal of Toxicology, Clinical Toxicology. Vol. 35, Pg. 321, 1997.

oral-man TDLo 2143 ug/kg/2D-
SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Annals of Pharmacotherpy. Vol. 33, Pg. 931, 1999.

oral-man TDLo 64 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Journal of Toxicology, Clinical Toxicology. Vol. 37, Pg. 634, 1999.

intraperitoneal-mouse LD50 230 mg/kg
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ANALGESIA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Pharmacy and Pharmacology. Vol. 29, Pg. 767, 1977.

oral-mouse LD50 544 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: ATAXIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 1, 1981.

intraperitoneal-rat LD50 210 mg/kg
BEHAVIORAL: TREMOR BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Pharmacy and Pharmacology. Vol. 29, Pg. 767, 1977.

oral-rat LD50 482 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA
Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 1, 1981.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
pharmaceuticals / chemical synthisis
Recommendation for bupropion hydrochloride usage levels up to:
 not for fragrance use.
 
Recommendation for bupropion hydrochloride flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :62884
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one;hydrochloride
Chemidplus:0031677937
RTECS:UG8858000 for cas# 31677-93-7
 
References:
 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one;hydrochloride
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):62884
Pubchem (sid):135019775
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):D00817
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2921.49.5000
MedlinePlusSupp:View
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
•bupropion is availible in 75- and 100-mg tablets. •wellbutrin; zyban
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 amfebutamone hydrochloride
 bupropionhydrochloride
2-[(tert-butyl)amino]-1-(3-chlorophenyl)propan-1-one, chloride
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one HCl
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride (1:1)
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one;hydrochloride
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-onehydrochloride
2-(tert-butylamino)-1-(3-chlorphenyl)propan-1-onhydrochlorid
(±)-2-(tert-butylamino)-3'-chloropropiophenone hydrochloride
2-(tert-butylamino)-3'-chloropropiophenone hydrochloride
m-chloro-a-tert-butylaminopropionphenone hydrochloride
m-chloro-a-tert-butylaminopropiophenone hydrochloride
1-(3-chlorophenyl)-2-(tert-butylamino)propan-1-one
(±)-1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone hydrochloride
1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone hydrochloride
1-(3-chlorophényl)-2-[(1,1-diméthyléthyl)amino]propan-1-one chlorhydrate
 elontril
1-propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-, hydrochloride, (±)-
1-propanone, 1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-, hydrochloride
1-propanone, 1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-, hydrochloride (1:1)
 quomem
 voxra
 wellbutrin
 wellbutrin SR
 wellbutrin XL
 wellbutrin XR
 zyban
 

Articles:

Info:Zyban (Bupropion)
PubMed:An Electronic Health Records Study of Long-Term Weight Gain Following Antidepressant Use.
PubMed:Charcoal hemoperfusion in bupropion overdose.
PubMed:Liquid chromatographic determinations of meta-chlorobenzoic acid in bupropion hydrochloride.
PubMed:An open-label, rater-blinded, 8-week trial of bupropion hydrochloride extended-release in patients with major depressive disorder with atypical features.
PubMed:Assessment of Potential In vitro Genotoxic and Cytotoxic Effects of Bupropion Hydrochloride (Wellbutrin) in Human Peripheral Lymphocytes and Human Cortical Neuron.
PubMed:Current and emerging pharmacotherapeutic options for smoking cessation.
PubMed:Effects of varenicline and bupropion sustained-release use plus intensive smoking cessation counseling on prolonged abstinence from smoking and on depression, negative affect, and other symptoms of nicotine withdrawal.
PubMed:Structural and energetic aspects of a new bupropion hydrochloride polymorph.
PubMed:Bupropion for smoking cessation in patients with acute coronary syndrome.
PubMed:Application of ion-pair complexation reaction for the spectrophotometric determination of bupropion hydrochloride in pharmaceuticals.
PubMed:Effect of bupropion treatment on brain activation induced by cigarette-related cues in smokers.
PubMed:Low dose of bupropion significantly enhances the anticonvulsant activity of felbamate, lamotrigine and topiramate in mice.
PubMed:Twenty percent of a representative sample of patients taking bupropion have abnormal, asymptomatic electroencephalographic findings.
PubMed:Bupropion and cognitive behavioral therapy for weight-concerned women smokers.
PubMed:Comparative effectiveness of 5 smoking cessation pharmacotherapies in primary care clinics.
PubMed:Electroencephalographic and behavioral convulsant effects of hydrobromide and hydrochloride salts of bupropion in conscious rodents.
PubMed:Structures from powders: bupropion hydrochloride.
PubMed:An investigation of bupropion substitution for the interoceptive stimulus effects of nicotine.
PubMed:Four years' follow up at a smoking cessation clinic.
PubMed:Cost-effective primary care-based strategies to improve smoking cessation: more value for money.
PubMed:Effect of increasing intraperitoneal infusion rates on bupropion hydrochloride-induced seizures in mice.
PubMed:Convulsive liability of bupropion hydrochloride metabolites in Swiss albino mice.
PubMed:Smoking cessation interventions for hospitalized smokers: a systematic review.
PubMed:Alcohol significantly lowers the seizure threshold in mice when co-administered with bupropion hydrochloride.
PubMed:Selecting among second-step antidepressant medication monotherapies: predictive value of clinical, demographic, or first-step treatment features.
PubMed:Bupropion hydrochloride versus placebo, in combination with cognitive behavioral therapy, for the treatment of cocaine abuse/dependence.
PubMed:Molecular genetics of successful smoking cessation: convergent genome-wide association study results.
PubMed:Australian smokers' use of bupropion and nicotine replacement therapies and their relation to reimbursement, Australia 2001-05.
PubMed:Depressive symptoms and smoking cessation after hospitalization for cardiovascular disease.
PubMed:Bupropion efficacy for smoking cessation is influenced by the DRD2 Taq1A polymorphism: analysis of pooled data from two clinical trials.
PubMed:Randomized, double-blind, placebo-controlled trial of 2 dosages of sustained-release bupropion for adolescent smoking cessation.
PubMed:Extended-release bupropion induced grand mal seizures.
PubMed:A double-blind, placebo-controlled, randomized trial of bupropion for smoking cessation in primary care.
PubMed:Short-term naturalistic treatment outcomes in cigarette smokers with substance abuse and/or mental illness.
PubMed:A preliminary investigation of naltrexone augmentation of bupropion to stop smoking with less weight gain.
PubMed:The effect of acute bupropion on sexual motivation and behavior in the female rat.
PubMed:Impact of publicity concerning pediatric suicidality data on physician practice patterns in the United States.
PubMed:Factors influencing glycemic control in type 2 diabetes during acute- and maintenance-phase treatment of major depressive disorder with bupropion.
PubMed:Bupropion hydrochloride produces conditioned hyperactivity in rats.
PubMed:Review of the pharmacology and clinical profile of bupropion, an antidepressant and tobacco use cessation agent.
PubMed:State Medicaid coverage for tobacco-dependence treatments--United States, 2005.
PubMed:Smoking cessation with varenicline, a selective alpha4beta2 nicotinic receptor partial agonist: results from a 7-week, randomized, placebo- and bupropion-controlled trial with 1-year follow-up.
PubMed:Six-month trial of bupropion with contingency management for cocaine dependence in a methadone-maintained population.
PubMed:Bupropion for major depressive disorder: Pharmacokinetic and formulation considerations.
PubMed:The influence of depressive symptoms on smoking cessation among African Americans in a randomized trial of bupropion.
PubMed:Bupropion SR for the treatment of substance-abusing outpatient adolescents with attention-deficit/hyperactivity disorder and mood disorders.
PubMed:Efficacy of bupropion and nortriptyline for smoking cessation among people at risk for or with chronic obstructive pulmonary disease.
PubMed:Executive summary: nicotine addiction.
PubMed:Cost-effectiveness of evidence-based pharmacotherapy or cognitive behavior therapy compared with community referral for major depression in predominantly low-income minority women.
PubMed:Oxygen as a therapy for reducing nicotine withdrawal symptoms.
PubMed:[Preparation and evaluation of 2,6-di-O-pentyl-beta-cyclodextrin bonded silica stationary phase for high performance liquid chromatography].
PubMed:Frequency of physician-directed assistance for smoking cessation in patients receiving cessation medications.
PubMed:[Safety of Zyban administration in nicotine dependence treatment].
PubMed:Should nortriptyline be used as a first-line aid to help smokers quit? Results from a systematic review and meta-analysis.
PubMed:The relationship between antidepressant medication use and rate of suicide.
PubMed:[Acute psychosis after administration of bupropion hydrochloride (Zyban)].
PubMed:Smokeless tobacco and cardiovascular risk.
PubMed:Bupropion for smoking cessation: a randomized trial.
PubMed:Convulsant and anticonvulsant effects of bupropion in mice.
PubMed:Pharmacokinetics of bupropion and its metabolites in haemodialysis patients who smoke. A single dose study.
PubMed:[Bupropion-induced epileptic seizures].
PubMed:A multicenter, randomized, double-blind, placebo-controlled, 6-month trial of bupropion hydrochloride sustained-release tablets as an aid to smoking cessation in hospital employees.
PubMed:Does the DRD2-Taq1 A polymorphism influence treatment response to bupropion hydrochloride for reduction of the nicotine withdrawal syndrome?
PubMed:Predicting adoption of home smoking restriction by inner-city black smokers.
PubMed:Effectiveness of bupropion sustained release for smoking cessation in a health care setting: a randomized trial.
PubMed:Zyban-- is there a cause for concern?
PubMed:Review of bupropion for smoking cessation.
PubMed:Bupropion overdose: QTc prolongation and its clinical significance.
PubMed:Treatment of nicotine dependence with bupropion SR: review of its efficacy, safety and pharmacological profile.
PubMed:Bupropion SR for smoking cessation.
PubMed:Bupropion: pharmacological and clinical profile in smoking cessation.
PubMed:Thrombotic thrombocytopenic purpura-hemolytic uremic syndrome after bupropion treatment for smoking cessation.
PubMed:Bupropion poisoning: a case series.
PubMed:Acute psychosis after administration of bupropion hydrochloride (Zyban).
PubMed:Direct evidence of facilitative actions of dopamine in the medial preoptic area on reflexive and noncontact erections in male rats.
PubMed:Clinical effectiveness of sustained-release bupropion and behavior therapy for tobacco dependence in a clinical setting.
PubMed:Gateways to Clinical Trials.
PubMed:Psychological intervention and antidepressant treatment in smoking cessation.
PubMed:Sustained-release bupropion for smoking cessation in African Americans: a randomized controlled trial.
PubMed:Bupropion sustained release. A therapeutic review of Zyban.
PubMed:Sustained-release bupropion overdose: a new entity for Australian emergency departments.
PubMed:Effects of gender on relapse prevention in smokers treated with bupropion SR.
PubMed:Bupropion (Zyban) toxicity.
PubMed:Acute doses of d-amphetamine and bupropion increase cigarette smoking.
PubMed:Bupropion hydrochloride: the development of a chiral separation using an ovomucoid column.
PubMed:Economic model of sustained-release bupropion hydrochloride in health plan and work site smoking-cessation programs.
PubMed:A clinical practice guideline for treating tobacco use and dependence: A US Public Health Service report. The Tobacco Use and Dependence Clinical Practice Guideline Panel, Staff, and Consortium Representatives.
PubMed:The use of bupropion hydrochloride for smoking cessation therapy.
PubMed:Pharmacotherapy of smoking cessation.
PubMed:Lack of effect of cimetidine on the pharmacokinetics of sustained-release bupropion.
PubMed:Bupropion hydrochloride induced serum sickness-like reaction.
PubMed:Recent advances in the pharmacotherapy of smoking.
PubMed:Smoking cessation: Part 2--Pharmacologic approaches.
PubMed:Reversal of atypical depression, sleepiness, and REM-sleep propensity in narcolepsy with bupropion.
PubMed:Pharmacokinetics of bupropion and its metabolites in cigarette smokers versus nonsmokers.
PubMed:Bupropion hydrochloride in attention deficit disorder with hyperactivity.
PubMed:Amplitude/intensity functions of auditory event-related potentials predict responsiveness to bupropion in major depressive disorder.
PubMed:The cardiovascular effects of bupropion and nortriptyline in depressed outpatients.
PubMed:Organic mental disorders associated with bupropion in three patients.
PubMed:Disposition of bupropion in healthy volunteers and subjects with alcoholic liver disease.
PubMed:Antidepressants reduce whole-body norepinephrine turnover while enhancing 6-hydroxymelatonin output.
PubMed:Bupropion in depression. II. The role of metabolites in clinical outcome.
PubMed:Bupropion in depression. I. Biochemical effects and clinical response.
PubMed:Pharmacologic modification of psychosexual dysfunction.
PubMed:Adverse reactions to five new antidepressants.
PubMed:The effect of experimentally-induced renal failure on accumulation of bupropion and its major basic metabolites in plasma and brain of guinea pigs.
PubMed:The disposition of bupropion and its metabolites in healthy male volunteers after single and multiple doses.
PubMed:Bupropion hydrochloride.
PubMed:Alcohol and bupropion pharmacokinetics in healthy male volunteers.
PubMed:Evaluation of bupropion hydrochloride: the first of a new class of atypical antidepressants.
PubMed:Review of bupropion.
PubMed:Bupropion: clinical assay for amphetamine-like abuse potential.
PubMed:Radioimmunoassay and pharmacokinetic profile of bupropion in the dog.
PubMed:Pharmacokinetics of bupropion, a novel antidepressant agent, following oral administration to healthy subjects.
PubMed:A comparison of bupropion hydrochloride with dexamphetamine and amitriptyline in healthy subjects.
PubMed:Bupropion hydrochloride ((+/-) alpha-t-butylamino-3-chloropropiophenone HCl): a novel antidepressant agent.
 
Notes:
a unicyclic, aminoketone antidepressant. the mechanism of its therapeutic actions is not well understood, but it does appear to block dopamine uptake. the hydrochloride is available as an aid to smoking cessation treatment.
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