Chemical Properties
White Solid
Uses
A metabolite of Venlafaxine (V120000), a selective serotonin noradrenaline reuptake inhibitor (SNRI). 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, a selective serotonin noradrenaline reuptake inhibitor. 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.
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.
Originator
Wyeth (United States)
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.
