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H3167

Sigma-Aldrich

(2S,3S)-Hydroxybupropion hydrochloride

≥98% (HPLC)

Synonym(e):

(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

Empirische Formel (Hill-System):
C13H18ClNO2 · HCl
CAS-Nummer:
106083-71-0
Molekulargewicht:
292.20
MDL-Nummer:
MFCD10565921
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329815193
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Lagerbedingungen

desiccated

Farbe

white to tan

Löslichkeit

DMSO: ≥12 mg/mL

Lagertemp.

−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

InChIKey

ORXTVTDGPVINDN-BTJVGWIPSA-N

Allgemeine Beschreibung

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

Biochem./physiol. Wirkung

(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.

Leistungsmerkmale und Vorteile

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.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H319

Gefahreneinstufungen

Eye Irrit. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
035M4766V
014M4741V
052M4712V
041M4728V

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Sigma-Aldrich

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Artikel

Biogenic Amine Transporters

These distinct transporters, NET, DAT and SERT, respectively, are of particular clinical interest because they are the molecular targets for many antidepressants as well as drugs of abuse, such as cocaine and the amphetamines.

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