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 (IC
50＝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
Originator
Wyeth (United States)
Uses
A metabolite of Venlafaxine, a selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant
Uses
a metabolite of Venlafaxine .;Labeled Venlafaxine, intended for use as an internal standard for the quantification of Venlafaxine by GC- or LC-mass spectrometry.
Uses
A metabolite of Venlafaxine (V120000), a selective serotonin noradrenaline reuptake inhibitor (SNRI). Used as an antidepressant.
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.
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.
