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B102

Bupropion hydrochloride

Name: Bupropion hydrochloride
Brand: SIGMA

≥98% (HPLC), solid, dopamine and norepinephrine transporter inhibitor

Synonym(s):

(±)-1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone hydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₁₃H₁₈ClNO · HCl

CAS Number:

31677-93-7

Molecular Weight:

276.20

NACRES:

NA.77

PubChem Substance ID:

24277884

UNSPSC Code:

12352200

EC Number:

250-759-9

MDL number:

MFCD00055209

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

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Properties

Product Name

Bupropion hydrochloride, ≥98% (HPLC), solid

description

Drug Control: Kábítószer / Narcotic Drug (Hungary), 78/2022. (XII. 28.) BM rendelet

Quality Level

100

assay

≥98% (HPLC)

form

solid

drug control

Kábítószer / Narcotic Drug (Hungary), 78/2022. (XII. 28.) BM rendelet

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)

Description

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

Inhibits the dopamine and norepinephrine transporters with K_is of 2.8 μM and 1.4 μM, respectively. Does not inhibit the serotonin transporter (K_i = 45 μM). Antidepressant.

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.

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.

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pictograms

GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Behavioral and biochemical effects of the antidepressant bupropion (Wellbutrin): evidence for selective blockade of dopamine uptake in vivo.

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

Smoking cessation treatment and risk of depression, suicide, and self harm in the Clinical Practice Research Datalink: prospective cohort study.

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

Bupropion for smoking cessation in patients hospitalized with cardiovascular disease: a systematic review and meta-analysis of randomized controlled trials.

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

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