O-Desmethylvenlafaxine Property

Melting point:

208-213°C

Boiling point:

403.8±25.0 °C(Predicted)

Density 

1.115±0.06 g/cm3(Predicted)

Flash point:

9℃

storage temp. 

2-8°C

solubility 

insoluble in EtOH; ≥13.2 mg/mL in DMSO; ≥2.45 mg/mL in EtOH

pka

10.04±0.26(Predicted)

form 

Solid

color 

White to off-white

InChIKey

KYYIDSXMWOZKMP-UHFFFAOYSA-N

LogP

0.33 at 25℃ and pH6

Safety

Hazard Codes 

F,T,Xi

Risk Statements 

11-23/24/25-39/23/24/25-36

Safety Statements 

7-16-36/37-45-26

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

3

RTECS 

GV8872620

HS Code 

29225090

Hazardous Substances Data

93413-62-8(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

O-Desmethylvenlafaxine Chemical Properties,Usage,Production

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

Originator

Wyeth (United States)

Uses

A metabolite of Venlafaxine, a selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant

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.

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.