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H3167

Sigma-Aldrich

(2S,3S)-Hydroxybupropion hydrochloride

≥98% (HPLC)

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C13H18ClNO2 · HCl
Número de CAS:
106083-71-0
Peso molecular:
292.20
Número MDL:
MFCD10565921
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
329815193
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

condiciones de almacenamiento

desiccated

color

white to tan

solubilidad

DMSO: ≥12 mg/mL

temp. de almacenamiento

−20°C

cadena SMILES

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

Clave InChI

ORXTVTDGPVINDN-BTJVGWIPSA-N

Descripción general

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

Acciones bioquímicas o fisiológicas

(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.

Características y beneficios

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.

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H319

Clasificaciones de peligro

Eye Irrit. 2

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000310144
0000313204
0000313205
0000244026
0000191657

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Yating Deng et al.
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Gentiopicroside (GE), a naturally occurring iridoid glycoside, has been developed into a Novel Traditional Chinese Drug named gentiopicroside injection, and it was approved for the treatment of acute jaundice and chronic active hepatitis by SFDA. However, the inhibitory and inducible
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
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
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
Rajesh Chavan et al.
Xenobiotica; the fate of foreign compounds in biological systems, 51(3), 251-261 (2020-10-21)
Nafithromycin is a next generation lactone ketolide antibiotic slated to enter phase III clinical development in India for the treatment of CABP as a shorter 800 mg-OD X3 day therapeutic regimen. Nafithromycin exhibits potent activity against MDR Streptococcus pneumoniae including erythromycin and

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