93413-62-8 Usage
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.
Chemical Properties
White Solid
Uses
Different sources of media describe the Uses of 93413-62-8 differently. You can refer to the following data:
1. A metabolite of Venlafaxine, a selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant
2. A metabolite of Venlafaxine (V120000), a selective serotonin noradrenaline reuptake inhibitor (SNRI). Used as an antidepressant.
3. a metabolite of Venlafaxine .;Labeled Venlafaxine, intended for use as an internal standard for the quantification of Venlafaxine by GC- or LC-mass spectrometry.
Definition
ChEBI: A tertiary amino compound that is N,N-dimethylethanamine substituted at position 1 by a 1-hydroxycyclohexyl and 4-hydroxyphenyl group. It is a metabolite of the drug venlafaxine.
Brand name
Pristiq
General Description
An analytical reference standard applicable for use as starting material in calibrators or controls for a variety of LC/MS or GC/MS applications such as urine drug testing, forensic analysis, or clinical toxicology. Also known as desvenlafaxine, O-desmethylvenlafaxine is an SNRI antidepressant marketed under the trade name Pristiq? for the treatment of depression. O-desmethylvenlafaxine is also a major urinary metabolite of venlafaxine, an SNRI antidepressant sold as Effexor? or Efexor and used to treat major depressive disorder, generalized anxiety disorder, and other anxiety disorders associated with depression.
Synthesis
Desvenlafaxine is chemically derived from 4-benzyloxyphenylacetic acid, by first converting to the acid chloride with oxalyl chloride and then condensing with dimethylamine to produce the corresponding N,N-dimethyl amide. Deprotonation of the amide with butyllithium, followed by condensation with cyclohexanone gives a b-hydroxyamide intermediate, which is reduced with alane, and debenzylated by using palladium on carbon and 1,4-cyclohexadiene to produce desvenlafaxine.
Check Digit Verification of cas no
The CAS Registry Mumber 93413-62-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,3,4,1 and 3 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 93413-62:
(7*9)+(6*3)+(5*4)+(4*1)+(3*3)+(2*6)+(1*2)=128
128 % 10 = 8
So 93413-62-8 is a valid CAS Registry Number.
InChI:InChI=1/C16H25NO2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16/h6-9,15,18-19H,3-5,10-12H2,1-2H3
93413-62-8Relevant articles and documents
3-Mercaptopropionic acid as a new reagent for the industrially applicable synthesis of highly pure O -desmethylvenlafaxine from venlafaxine
Furlan, Borut,?asar, Zdenko,?terk, Damjan,Fabris, Jan
, p. 67 - 73 (2015)
3-Mercaptopropionic acid was introduced as a cheap new O-demethylating agent as exemplified by its application in the synthesis of antidepressant O-desmethylvenlafaxine from venlafaxine. The application of 3-mercaptopropionic acid allowed high conversion of venlafaxine to O-desmethylvenlafaxine and a facile workup, which enabled the isolation of the desired O-desmethylvenlafaxine with a high >99.8% chromatographic purity and 76% yield by a simple extractive workup followed by the precipitation.
Functional and structural characterisation of common cytochrome P450 2D6 allelic variants—roles of Pro34 and Thr107 in catalysis and inhibition
Dong, Amelia Nathania,Ahemad, Nafees,Pan, Yan,Palanisamy, Uma Devi,Yiap, Beow Chin,Ong, Chin Eng
, p. 1015 - 1029 (2019/05/07)
One major source of inter-individual variability in drug pharmacokinetics is genetic polymorphism of the cytochrome P450 (CYP) genes. This study aimed to elucidate the enzyme kinetic and molecular basis for altered activity in three major alleles of CYP2D6, namely CYP2D6*2, CYP2D6*10 and CYP2D6*17. The E. coli-expressed allelic variants were examined using substrate (venlafaxine and 3-cyano-7-ethoxycoumarin[CEC]) and inhibitor (quinidine, fluoxetine, paroxetine, terbinafine) probes in enzyme assays as well as molecular docking. The kinetics data indicated that R296C and S486T mutations in CYP2D6*2 have caused enhanced ligand binding (enhanced intrinsic clearance for venlafaxine and reduced IC50 for quinidine, paroxetine and terbinafine), suggesting morphological changes within the active site cavity that favoured ligand docking and binding. Mutations in CYP2D6*10 and CYP2D6*17 tended to cause deleterious effect on catalysis, with reduced clearance for venlafaxine and CEC. Molecular docking indicated that P34S and T107I, the unique mutations in the alleles, have negatively impacted activity by affecting ligand access and binding due to alteration of the substrate access channel and active site morphology. IC50 values however were quite variable for quinidine, fluoxetine and terbinafine, and a general decrease in IC50 was observed for paroxetine, suggesting ligand-specific altered susceptibility to inhibition in the alleles. This study indicates that CYP2D6 allele selectivity for ligands was not solely governed by changes in the active site architecture induced by the mutations, but that the intrinsic properties of the substrates and inhibitors also played vital role.
A PROCESS FOR PREPARATION OF1-[2-(DIMETHYLAMINO)-1-(4-HYDROXYPHENYL) ETHYL]-CYCLOHEXANOL AND SALTS THEREOF
-
Page/Page column 10, (2018/09/08)
The present invention relates to a high yield process of preparation of, [1-[2-(Dimethylamino)-1- (4-hydroxyphenyl)ethyl]-cyclohexanol]through potassium hydroxide mediated demethylation of [1-[2-(Dimethyl amino-1-(4-methoxyphenyl) ethyl cyclohexanol]in monoethylene glycol under phase transfer conditions. The invention also relates to preparation of salt of [1-[2- (Dimethylamino)-1-(4-hydroxyphenyl)ethyl]-cyclohexanol].
