192374-15-5

Basic information

• Product Name: (R,R)-Hydroxy Bupropion
• Synonyms: (R,R)-Hydroxy Bupropion;(2R,3R)-;Bupropion Morpholinol (2R,3R)-Isomer;(R,R)-Hydroxy Bupropion Hydrochloride
• CAS NO: 192374-15-5
• Molecular Formula: C₁₃H₁₈ClNO₂
• Molecular Weight: 255.74052
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Chiral Reagents, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 192374-15-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 117-119°C
• Boiling Point: 386.574°C at 760 mmHg
• Flash Point: 187.594°C
• Appearance: /
• Density: 1.144g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• Stability: Hygroscopic
• CAS DataBase Reference: (R,R)-Hydroxy Bupropion(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-Hydroxy Bupropion(192374-15-5)
• EPA Substance Registry System: (R,R)-Hydroxy Bupropion(192374-15-5)

Safety Data

• Hazardous Substances Data: 192374-15-5(Hazardous Substances Data)

Usage

Chemical Properties

Light Beige Solid

Uses

(R,R) Enantiomer metabolite of Bupropion (B689625), an antidepressant.

InChI:InChI=1/C13H18ClNO2/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/t9-,13+/m1/s1

Upstream product

• 124-68-5 2-Amino-2-methyl-1-propanol 
• 291275-47-3 Trifluoro-methanesulfonic acid (S)-2-(3-chloro-phenyl)-1-methyl-2-oxo-ethyl ester 
• 291275-45-1 (Z)-tert-butyl-[1-(3-chlorophenyl)prop-1-enyloxy]dimethylsilane 
• 287477-53-6 (S)-1-(3-chlorophenyl)-2-hydroxypropan-1-one 
• 34841-35-5 3'-chloro-propiophenone 

Relevant articles and documents

HYDROXYBUPROPION ANALOGUES FOR TREATING DRUG DEPENDENCE

The invention provides hydroxybupropion analogues capable of inhibiting the reuptake of one or more monoamines and/or acting as antagonists at nicotinic acetylcholine receptors. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine, and serotonin and/or may selectively bind to one or more nicotinic acetylcholine receptor subtypes. Such compounds may be used to treat conditions that are responsive to modification of monoamine levels and/or antagonism of nicotinic acetylcholine receptors, including drug dependency, depression, and obesity.

Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate

A stereospecific method for the synthesis of enantiopure α-aminoketone from its corresponding α-hydroxy-ketone via the triflate intermediate is discussed. This strategy provides a rapid and efficient route for the preparation of either enantiomer of bupro