Accéder au contenu
Merck
Toutes les photos(1)

Key Documents

View All Documentation

H3167

Sigma-Aldrich

(2S,3S)-Hydroxybupropion hydrochloride

≥98% (HPLC)

Synonyme(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

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
Toutes les photos(1)

About This Item

Formule empirique (notation de Hill):
C13H18ClNO2 · HCl
Numéro CAS:
106083-71-0
Poids moléculaire :
292.20
Numéro MDL:
MFCD10565921
Code UNSPSC :
12352200
ID de substance PubChem :
329815193
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to tan

Solubilité

DMSO: ≥12 mg/mL

Température de stockage

−20°C

Chaîne 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

Clé InChI

ORXTVTDGPVINDN-BTJVGWIPSA-N

Description générale

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

Actions biochimiques/physiologiques

(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.

Caractéristiques et avantages

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H319

Classification des risques

Eye Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

Déjà en possession de ce produit ?

Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Yating Deng et al.
Drug metabolism and pharmacokinetics, 28(4), 339-344 (2013-02-20)
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
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

Articles

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.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique