300827-87-6

Basic information

• Product Name: 4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]-phenol hydrochloride
• Synonyms: 4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]-phenol hydrochloride;Desvenlafaxine hydrochloride
• CAS NO: 300827-87-6
• Molecular Formula: C₁₆H₂₅NO₂*ClH
• Molecular Weight: 0
• Mol File: 300827-87-6.mol

Chemical Properties

• Appearance: white to off-white/
• Storage Temp.: 2-8°C
• Solubility: DMSO: >20mg/mL
• Stability: Hygroscopic
• CAS DataBase Reference: 4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]-phenol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]-phenol hydrochloride(300827-87-6)
• EPA Substance Registry System: 4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]-phenol hydrochloride(300827-87-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 300827-87-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]-phenol hydrochloride is used as an active pharmaceutical ingredient for the development of medications targeting specific medical conditions. Its unique structure allows it to interact with biological targets, such as receptors or enzymes, to elicit desired therapeutic effects.
Used in Antidepressant Development:
In the field of antidepressant research, 4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]-phenol hydrochloride is used as a selective serotonin noradrenaline reuptake inhibitor (SNRI). It works by blocking the reuptake of serotonin and noradrenaline in the brain, thereby increasing their levels and improving mood and reducing symptoms of depression.
Used in Environmental Research:
4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]-phenol hydrochloride has been utilized in studies to evaluate its potential effects on neuronal gene expression when present in drinking water at environmental concentrations. This research helps to understand the compound's impact on human health and the environment, contributing to the development of safety guidelines and regulations.
Used in Drug Delivery Systems:
Similar to gallotannin, 4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]-phenol hydrochloride can also be employed in the development of novel drug delivery systems. These systems aim to improve the compound's delivery, bioavailability, and therapeutic outcomes by using various organic and metallic nanoparticles as carriers.

Biochem/physiol Actions

Desvenlafaxine hydrochloride is a dual SERT/NET reuptake inhibitor. It is a major active metabolite of venlafaxine (#542); brain penetrant; Ki = 40 nM and 122 nM for hSERT and hNET, respectively (weak binding at the hDAT). Inhibition of [3H]5-HT or [3H]NE uptake for the hSERT or hNET produced IC50 values of 47 and 531 nM.

Upstream product

• 93413-69-5 1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol 
• 99300-78-4 venlafaxine hydrochloride 
• 93413-62-8 O-desmethylvenlafaxine 

Downstream Products

• 93414-04-1 (+/-)-1-[2-dimethylamino-1-(4-hydroxyphenyl)-ethyl]-cyclohexanol fumarate 
• 93413-62-8 O-desmethylvenlafaxine 

Relevant articles and documents

A hydrochloride desvenlafaxine method for the preparation of

The invention relates to a preparation method of desvenlafaxine hydrochloride. The preparation method comprises the following steps: adding venlafaxine hydrochloride into methanesulfonic acid, and adding a demethylation reagent methionine. The preparation method provided by the invention is green and environment-friendly while the temperature is not high, few byproducts are generated and the product quality is good; and moreover, the yield is over 88%, and the purity reaches 99.9%.

Crystalline venlafaxine metabolite and preparation method thereof

The invention relates to a crystalline venlafaxine metabolite and a preparation method thereof. The crystalline venlafaxine metabolite provided by the invention is a hydrate, and the hydrate is a hydrochloride hydrate crystal form. The invention also provides a preparation method thereof. The method includes: reacting corresponding free alkali with a hydrochloric acid aqueous solution to obtain a salt, adding a seed crystal and a poor solvent to obtain high purity crystal form of the hydrochloride hydrate. The hydrate provided by the invention has good stability, is convenient for production, transportation and storage, and can meet all requirements for a preparation raw material.

PROCESS FOR THE PREPARATION OF DESVENLAFAXINE AND PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALTS THEREOF

The present invention relates to a process for the preparation of desvenlafaxine or a pharmaceutically acceptable acid addition salt thereof, based on the demethylation of venlafaxine by the use of alkyl aluminium or alkyl aluminium hydride compounds, particularly TIBA and DIBAL.

Preparation of O-desmethylvenlafaxine salts

The present invention relates to a process for the preparation of a salt of O-desmethylvenlafaxine comprising a) dissolving or suspending O-desmethylvenlafaxine in the form of its base in a liquid medium selected from the group of solvents and suspending