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H3167

Sigma-Aldrich

(2S,3S)-Hydroxybupropion hydrochloride

≥98% (HPLC)

Synonym(s):

(2S,3S)-Hydroxybupropion hydrochloride, (+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride, (2S,3S)-2-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride, GW 353162, Radafaxine hydrochloride, SS-hydroxybupropion hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C13H18ClNO2 · HCl
CAS Number:
106083-71-0
Molecular Weight:
292.20
MDL number:
MFCD10565921
UNSPSC Code:
12352200
PubChem Substance ID:
329815193
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to tan

solubility

DMSO: ≥12 mg/mL

storage temp.

−20°C

SMILES string

Cl.C[C@@H]1NC(C)(C)CO[C@@]1(O)c2cccc(Cl)c2

InChI

1S/C13H18ClNO2.ClH/c1-9-13(16,17-8-12(2,3)15-9)10-5-4-6-11(14)7-10;/h4-7,9,15-16H,8H2,1-3H3;1H/t9-,13+;/m0./s1

InChI key

ORXTVTDGPVINDN-BTJVGWIPSA-N

General description

(2S,3S)-hydroxybupropion is a major metabolite of bupropion.

Biochem/physiol Actions

(2S,3S)-hydroxybupropion is a dopamine transporter (DAT) and norepinephrine transporter (NET) transporters inhibitor and nicotinic acetylcholine receptor (nAChR) family modulator. Hydroxybupropions were reported to contribute to antidepressant and perhaps smoking cessation activities. Both (2S,3S) and (2R,3R) metabolites reverse affective and somatic withdrawal signs in nicotine-dependent mice, but (2S,3S)-hydroxybupropion is more potent. (2S,3S)-hydroxybupropion significantly decreases the development of nicotine reward in mice.

Features and Benefits

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Matthew L Banks et al.
Behavioural pharmacology, 27(2-3 Spec Issue), 196-203 (2016-02-18)
The dopamine transporter (DAT) inhibitor and nicotinic acetylcholine (nACh) receptor antagonist bupropion is being investigated as a candidate 'agonist' medication for methamphetamine addiction. In addition to its complex pharmacology, bupropion also has two distinct pharmacologically active metabolites. However, the mechanism
E Malcolm et al.
Psychopharmacology, 232(15), 2763-2771 (2015-03-13)
Preclinical studies with bupropion in rodent models of nicotine dependence have generated equivocal findings with regard to translating the clinical efficacy of the antidepressant as a smoking cessation agent. Given that rats are poor metabolizers of bupropion, the present experiments
M Imad Damaj et al.
The Journal of pharmacology and experimental therapeutics, 334(3), 1087-1095 (2010-06-26)
Bupropion is an atypical antidepressant that also has utility as a smoking cessation aid. Hydroxybupropions are major metabolites of bupropion and are believed to contribute to antidepressant and perhaps smoking cessation activities. Because bupropion metabolism is more similar in humans
Rajesh Chavan et al.
Xenobiotica; the fate of foreign compounds in biological systems, 51(3), 251-261 (2020-10-21)
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