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B102

Sigma-Aldrich

Bupropion hydrochloride

≥98% (HPLC), solid

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Synonym(s):
(±)-1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone hydrochloride
Empirical Formula (Hill Notation):
C13H18ClNO · HCl
CAS Number:
31677-93-7
Molecular Weight:
276.20
EC Number:
250-759-9
MDL number:
MFCD00055209
UNSPSC Code:
12352200
PubChem Substance ID:
24277884
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

white

solubility

H2O: 15 mg/mL, clear

originator

GlaxoSmithKline

SMILES string

Cl[H].CC(NC(C)(C)C)C(=O)c1cccc(Cl)c1

InChI

1S/C13H18ClNO.ClH/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10;/h5-9,15H,1-4H3;1H

InChI key

HEYVINCGKDONRU-UHFFFAOYSA-N

Gene Information

human ... DRD1(1812) , DRD2(1813) , DRD3(1814) , DRD4(1815) , DRD5(1816) , SLC6A2(6530) , SLC6A3(6531)

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General description

Bupropion is structurally linked to the phenylethylamine family. It is a monocyclic aminoketone (chloropropiophenone).

Application

Bupropion hydrochloride has been used as an anti-depressant and injected into mice intraperitoneally for forced swim test. It has also been used to study its effects on depression, anxiety and smoking cessation.

Biochem/physiol Actions

Bupropion possesses antidepressant and anxiolytic properties. It serves as a good auxiliary for people who makes an effort to give up smoking. It may also be used in the treatment for attention-deficit hyperactivity disorder.
Inhibits the dopamine and norepinephrine transporters with Kis of 2.8 μM and 1.4 μM, respectively. Does not inhibit the serotonin transporter (Ki = 45 μM). Antidepressant.

Features and Benefits

This compound is a featured product for ADME Tox and Neuroscience research. Discover more featured ADME Tox and Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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B R Cooper et al.
The Journal of pharmacology and experimental therapeutics, 215(1), 127-134 (1980-10-01)
Bupropion (BW 323U; Wellbutrin), a novel compound with antidepressant effects in man, was found to reduce immobility in an "experimental helplessness" forced swimming antidepressant test in rats as did imipramine and amitriptyline. Higher doses produced elevated locomotor activity in an
Kyla H Thomas et al.
BMJ (Clinical research ed.), 347, f5704-f5704 (2013-10-15)
To compare the risk of suicide, self harm, and depression in patients prescribed varenicline or bupropion with those prescribed nicotine replacement therapy. Prospective cohort study within the Clinical Practice Research Datalink. 349 general practices in England. 119,546 men and women
Marney A White et al.
The Journal of clinical psychiatry, 74(4), 400-406 (2013-05-10)
Binge-eating disorder (BED) is defined by recurrent binge eating (eating unusually large quantities of food during which a subjective loss of control is experienced), marked distress about the binge eating, and the absence of inappropriate weight compensatory behaviors. BED is
Sonia M Grandi et al.
The Canadian journal of cardiology, 29(12), 1704-1711 (2013-11-26)
Smoking remains the most important modifiable risk factor for secondary prevention of cardiovascular events. We therefore performed a meta-analysis to determine the efficacy and safety of bupropion therapy started in-hospital for smoking cessation in patients with cardiovascular disease (CVD). We
Effects of bupropion on depression, anxiety and smoking cessation
Hernandez-Lozano M, et al.
Archives of Neuroscience, 15(4), 260-266 (2010)
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