Desvenlafaxine

Base Information

• Chemical Name: Desvenlafaxine
• CAS No.: 93413-62-8
• Molecular Formula: C16H25NO2
• Molecular Weight: 263.38
• Hs Code.: 29225090
• European Community (EC) Number: 700-516-2
• UNII: NG99554ANW
• DSSTox Substance ID: DTXSID40869118
• Nikkaji Number: J347.736C
• Wikipedia: Desvenlafaxine
• Wikidata: Q2419445
• NCI Thesaurus Code: C61703
• RXCUI: 734064
• Pharos Ligand ID: ZXZGA28FC1D5
• Metabolomics Workbench ID: 43681
• ChEMBL ID: CHEMBL1118
• Mol file: 93413-62-8.mol

Synonyms:2-(1-hydroxycyclohexyl)-2-((4-hydroxyphenyl)ethyl)dimethylammonium 3-carboxypropanoate monohydrate;4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol;45,233, WY;45233, WY;desvenlafaxine;desvenlafaxine succinate;Monohydrate, O-desmethylvenlafaxine Succinate;O desmethylvenlafaxine;O desmethylvenlafaxine Succinate;O desmethylvenlafaxine Succinate Monohydrate;O-desmethylvenlafaxine;O-desmethylvenlafaxine Succinate;O-desmethylvenlafaxine Succinate Monohydrate;Pristiq;Succinate Monohydrate, O-desmethylvenlafaxine;Succinate, Desvenlafaxine;Succinate, O-desmethylvenlafaxine;WY 45,233;WY 45233;WY-45,233;WY-45233;WY45,233;WY45233

Chemical Property of Desvenlafaxine

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 3.03E-07mmHg at 25°C
• Melting Point: 208-213 °C
• Refractive Index: 1.573
• Boiling Point: 403.8 °C at 760 mmHg
• PKA: 10.04±0.26(Predicted)
• Flash Point: 193.2 °C
• PSA: 43.70000
• Density: 1.115 g/cm³
• LogP: 2.73260
• Storage Temp.: -20°C Freezer
• Solubility.: insoluble in EtOH; ≥13.2 mg/mL in DMSO; ≥2.45 mg/mL in EtOH
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 263.188529040
• Heavy Atom Count: 19
• Complexity: 266

Purity/Quality:

99.9% ^*data from raw suppliers

D,L-O-DesmethylVenlafaxine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T,Xi
• Hazard Codes: F,T,Xi
• Statements: 11-23/24/25-39/23/24/25-36
• Safety Statements: 7-16-36/37-45-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC(C1=CC=C(C=C1)O)C2(CCCCC2)O
• Recent ClinicalTrials: A Comparative Study of Sage-217 Plus an Antidepressant (ADT) Versus Placebo Plus an ADT in Adults With Major Depressive Disorder
• Recent EU Clinical Trials: A randomised, double-blind, parallel-group, active controlled study evaluating the efficacy of vortioxetine versus desvenlafaxine in adult patients suffering from major depressive disorder with partial response to SSRI treatment
• Description: Desvenlafaxine is a new member of the SNRI class of antidepressants. It is marketed as an extended release tablet for once-daily oral treatment of MDD in adult patients. Desvenlafaxine (O-desmethylvenlafaxine) is the major active metabolite of the previously marketed antidepressant venlafaxine (Effexor). Similar to venlafaxine, desvenlafaxine is a more potent inhibitor of serotonin and norepinephrine reuptake (IC50＝47 and 531 nM, respectively) than that of dopamine (62% inhibition at 100 mM) in in vitro studies. It does not have significant in vitro affinity for other neurotransmitter reporters such as a1-adrenergic, H1-histaminergic, or muscarine-cholinergic receptors. Desvenlafaxine is marketed as a racemic mixture. Specific pharmacological properties of the enantiomers of desvenlafaxine have not been reported.
• Uses: A metabolite of Venlafaxine, a selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant A metabolite of Venlafaxine (V120000), a selective serotonin noradrenaline reuptake inhibitor (SNRI). Used as an antidepressant. a metabolite of Venlafaxine .;Labeled Venlafaxine, intended for use as an internal standard for the quantification of Venlafaxine by GC- or LC-mass spectrometry.

Technology Process of Desvenlafaxine

There total 32 articles about Desvenlafaxine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol (93413-69-5) → O-desmethylvenlafaxine (93413-62-8)

Guidance literature:

With potassium hydroxide; In ethylene glycol; at 195 - 200 ℃; for 24h; Inert atmosphere;

Reference yield: 98.0%

O-benzyldesvenlafaxine hydrochloride (1268269-56-2) → O-desmethylvenlafaxine (93413-62-8)

Guidance literature:

O-benzyldesvenlafaxine hydrochloride; With hydrogen; Raney nickel; methanol washed; In methanol; water; at 50 ℃; for 2h; under 37503.8 Torr;

With ammonia; In methanol; water; pH=9.5; Product distribution / selectivity;

Reference yield: 98.0%

venlafaxine hydrochloride → O-desmethylvenlafaxine (93413-62-8)

Guidance literature:

venlafaxine hydrochloride; With potassium carbonate; In polyethyleneglycol monomethylether; for 0.5h;

With 2-methyl-5-tert-butylthiophenol; In polyethyleneglycol monomethylether; at 175 ℃; Product distribution / selectivity; Inert atmosphere;

upstream raw materials:

4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenyl benzoate

N,N-Didesmethyldesvenlafaxine

formaldehyd

1-(2-amino-1-(4-methoxyphenyl)ethyl)cyclohexanol hydrochloride

Downstream raw materials:

[2-(1-hydroxycyclohexyl)-2-(4-hydroxyphenyl)ethyl]dimethylammonium 3-carboxypropanoate monohydrate

(-)-O-desmethylvenlafaxine hydrochloride

[²H]-desvenlafaxine

Refernces

• 1、 -. "Synthesis method of venlafaxine". Paragraph 0028; 0034; 0038-0039; 0043-0044; 0048. . Retrieved 2021/09/21.
• 2、 -. "Preparation method of demethylvenlafaxine succinate compound". Paragraph 0027; 0035; 0050; 0051; 0054. . Retrieved 2019/05/02.