149289-30-5

Usage

Uses

Used in Pharmaceutical Industry:
D,L N-Desmethylvenlafaxine is used as an antidepressant for the treatment of major depressive disorder. As a metabolite of Venlafaxine, it contributes to the overall therapeutic effects of the parent drug by inhibiting the reuptake of serotonin and noradrenaline in the brain, thereby increasing their levels and improving mood and reducing depressive symptoms.

InChI:InChI=1/C16H25NO2/c1-17-12-15(16(18)10-4-3-5-11-16)13-6-8-14(19-2)9-7-13/h6-9,15,17-18H,3-5,10-12H2,1-2H3

Upstream product

• 104-47-2 p-methoxybenzylnitrile 
• 272788-07-5 N-[2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]formamide 
• 93413-77-5 N,N-didesmethylvenlafaxine 
• 593-51-1 methylamine hydrochloride 
• 93413-76-4 1-[cyano(4-methoxyphenyl)methyl]cyclohexanol 
• 108-94-1 cyclohexanone 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 93413-90-2 N-Desmethylvenlafaxine hydrochloride 
• 135308-74-6 N-Desmethyldesvenlafaxine 

Relevant academic research and scientific papers

DERIVATIVES OF (-)-VENLAFAXINE AND METHODS OF PREPARING AND USING THE SAME

Methods of preparing, and compositions comprising, derivatives of (?)-venlafaxine are disclosed. Also disclosed are methods of treating and preventing diseases and disorders including, but not limited to, affective disorders such as depression, bipolar and manic disorders, attention deficit disorder, attention deficit disorder with hyperactivity, Parkinson's disease, epilepsy, cerebral function disorders, obesity and weight gain, incontinence, dementia and related disorders.

Impurity profile study of venlafaxine hydrochloride, an antipsychotic drug substance

Venlafaxine hydrochloride is a phenyl ethylamine derivative, used for the treatment of depression. During the process development of venlafaxine hydrochloride, six process-related potential impurities were detected in high-performance liquid chromatograph

AN IMPROVED PROCESS FOR THE PREPARATION OF VENLAFAXINE AND ITS ANALOGS

A novel single step process for the synthesis of venlafaxine of formula I and N-desmethylvenlafaxine of formula II from 2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)acetonitrile [cyano-intermediate] of formula V V comprising reacting 2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)acetonitrile with an alkylamine and/or its salt in a solvent in the presence of a transition metal catalyst, under hydrogen atmosphere.

2-Phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives: Synthesis and antidepressant activity

A series of 2-phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives was examined for the ability to inhibit both rat brain imipramine receptor binding and the synaptosomal uptake of norepinephrine (NE) and serotonin (5-HT). Neurotransmitter uptake inhibition was highest for a subset of 2-phenyl-2-(1-hydroxycyclohexyl)dimethylethylamines in which the aryl ring has a halogen or methoxy substituent at the 3- and/or 4-positions. Potential antidepressant activity in this subset was assayed in three rodent models - the antagonism of reserpine-induced hypothermia, the antagonism of histamine-induced ACTH release, and the ability to reduce noradrenergic responsiveness in the rat pineal gland. An acute effect seen in the rat pineal gland with several analogues, including 1-[1-(3,4-dichlorophenyl)-2-(dimethylamino)ethyl]cyclohexanol (23) and 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol (4), was taken as a possible correlate of a rapid onset of antidepressant activity. Compound 4 (venlafaxine) is presently undergoing clinical evaluation.