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B102

Sigma-Aldrich

Bupropion hydrochloride

≥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
EC Number:
250-759-9
MDL number:
MFCD00055209
UNSPSC Code:
12352200
PubChem Substance ID:
24277884
NACRES:
NA.77

Key Documents

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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)

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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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

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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Certificates of Analysis (COA)

Lot/Batch Number
105M4725V
063M4707V
031M4739V
019K4710
058K4711

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Effects of bupropion on depression, anxiety and smoking cessation
Hernandez-Lozano M, et al.
Archives of Neuroscience, 15(4), 260-266 (2010)
Chronic ethanol potentiates the effect of neuropeptide s in the basolateral amygdala and shows increased anxiolytic and anti-depressive effects
Enquist J, et al.
Neuropsychopharmacology, 37(11), 2436-2436 (2012)
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
Danielle Baribeau et al.
Journal of addiction medicine, 7(3), 216-217 (2013-03-23)
Bupropion is an antidepressant commonly prescribed as a smoking cessation aid. It has effects on dopamine and norepinephrine, and can lower seizure threshold, particularly in overdose. Several cases of recreational use of bupropion via nasal insufflation have been reported in
Michelle Hottinger et al.
American journal of law & medicine, 38(4), 667-689 (2013-01-30)
Generic drugs represent a significant portion of the medical arsenal in treating disease. As copies of originator drugs, these drugs have been permitted abbreviated approval under the Hatch-Waxman Act. Yet with the current cost focus upon generic formulations, potential safety
View All Related Papers

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