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Desvenlafaxine succinate

Desvenlafaxine succinate Structure
CAS No.
386750-22-7
Chemical Name:
Desvenlafaxine succinate
Synonyms
Pristiq;Unii-zb22enf0xr;WY 45233 succinate;Desvenla succinate;Desvenlafaxine succinate;Norvenlafaxine succinate;Pristiq succinate hydrate;C16H25NO2.HOOCCH2CH2COOH.H2O;Desvenlafaxine (succinate hydrate);Desvenlafaxine succinate USP/EP/BP
CBNumber:
CB01459766
Molecular Formula:
C20H31NO6
Molecular Weight:
381.47
MOL File:
386750-22-7.mol
MSDS File:
SDS
Modify Date:
2024/7/2 8:54:57

Desvenlafaxine succinate Properties

storage temp. Store at +4°C
solubility DMSO:3.0(Max Conc. mg/mL);7.51(Max Conc. mM)
form Powder
color White to off-white
Stability Hygroscopic

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
HS Code  2922504500
NFPA 704
0
2 0

Desvenlafaxine succinate Chemical Properties,Uses,Production

Description

Desvenlafaxine Succinate is a dual serotonin and norepinephrine reuptake inhibitor (SNRI) that was approved for the treatment of major depressive disorder (MDD) in the United States in 2008. In order to improve the efficacy and safety profile of venlafaxine, Wyeth discovered and developed one of the major metabolites of venlafaxine, namely the O-desmethyl metabolite (desvenlafaxine). Desvenlafaxine is also being developed for the treatment of moderate to severe vasomotor symptoms associated with menopause (i.e., hot flashes and night sweats) and is also in phase III clinical trials to study it’s effectiveness in treating fibromyalgia and neuropathic pain.

Uses

Antianxiety therapeutic

Synthesis

Desvenlafaxine has been prepared via two different routes, and both are described in the scheme. The first route involved simple demethylation of venlafaxine (67) using L-selectride in dimethoxyethane giving desvenlafaxine 68 as its free base in 91% yield. Compound 68 was then recrystallized with succinic acid in acetone/ water to give desvenlafaxine succinate (VIII) in 86% yield. An alternative method to prepare desvenlafaxine is described in the bottom portion of the scheme. 4-Benzyloxyphenylacetic acid 69 was converted to its corresponding acid chloride upon treatment with thionyl chloride and catalytic DMF in refluxing methylene chloride. The crude reaction mixture was added to a solution of dimethylamine hydrochloride and triethyl amine in methylene chloride at 5 ??C to give dimethylacetamide 70 in 90% yield. Deprotonation of 70 with LHMDS in THF at -70 ??C followed by addition of cyclohexanone gave alcohol 71 in 82% yield. Reduction of the acetamide with borane THF complex in refluxing THF produced dimethyl amine 72 in 66% yield. Catalytic hydrogenation in the presence of 20% Pd/C effected debenzylation of 72 to give desvenlafaxine free base 68 in 87% yield.

Synthesis_386750-22-7

Desvenlafaxine succinate Preparation Products And Raw materials

Raw materials

Preparation Products

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Desvenlafaxine succinate Spectrum

Desvenlafaxine succinate 4-(2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol succinate hydrate Desvenlafaxine succinate monohydrate Pristiq Unii-zb22enf0xr Desvenlafaxine (succinate hydrate) C16H25NO2.HOOCCH2CH2COOH.H2O 4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenolsuccinate WY 45233 succinate (1R)-2-(2-(diMethylaMino)-1-phenylethyl)cyclohexanol Desvenlafaxine (O-DesMethyl Venlafaxine) Succinate Monohydrate Butanedioic acid, compd. with 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol, hydrate (1:1:1) 4-(2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol succinate monohydrate 2-(1-Hydroxycyclohexyl)-2-(4-hydroxyphenyl)ethyl]dimethylammonium3-carboxypropanoatemonohydrate Desvenla succinate O-Desmethylvenlafaxine succinate hydrate Pristiq succinate hydrate PRISTIQ SUCCINATE HYDRATE;O-DESMETHYLVENLAFAXINE SUCCINATE HYDRATE Desvenlafaxine succinic acid monohydrate [2H6]-rac-O-Desmethyl Venlafaxine Succinate Hydrate Desvenlafaxine succinate USP/EP/BP RAC-O-DESMETHYL VENLAFAXINE-D6 SUCCINATE HYDRATE Desvenlafaxine succinateQ: What is Desvenlafaxine succinate Q: What is the CAS Number of Desvenlafaxine succinate Q: What is the storage condition of Desvenlafaxine succinate Q: What are the applications of Desvenlafaxine succinate TIANFUCHEM-- Desvenlafaxine succinate Desvenlafaxine Succinate (1-[2-(Dimethylamino)-1-(4-hydroxyphenyl)ethyl]cyclohexanol hydrogen butanedioate monohydrate) (1175773) Norvenlafaxine succinate 386750-22-7 00-00-3 C16H25NO2C4H6O4 C16H25NO2C4H6O4H2O C20H33NO7 Inhibitors APIs