93413-44-6

Basic information

• Product Name: S-VENLAFAXINE
• Synonyms: S-VENLAFAXINE;Venlafaxine S-Isomer;(1S)-[2-Dimethylamino-1-(4-methoxyphenyl) ethyl] cyclohexanol
• CAS NO: 93413-44-6
• Molecular Formula: C₁₇H₂₇NO₂
• Molecular Weight: 277.4
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 93413-44-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 102-104°C
• Boiling Point: 397.575°C at 760 mmHg
• Flash Point: 194.246°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly, Sonicated), Ethanol (Slightly), Ethyl Ace
• PKA: 14.84±0.20(Predicted)
• CAS DataBase Reference: S-VENLAFAXINE(CAS DataBase Reference)
• NIST Chemistry Reference: S-VENLAFAXINE(93413-44-6)
• EPA Substance Registry System: S-VENLAFAXINE(93413-44-6)

Safety Data

• Hazardous Substances Data: 93413-44-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

S-Venlafaxine is a optically active version of Venlafaxine, a selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant.

InChI:InChI=1/C17H27NO2/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14/h7-10,16,19H,4-6,11-13H2,1-3H3/t16-/m1/s1

Upstream product

• 941592-54-7 (2R)-2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)-N,N-dimethylacetamide 
• 93413-69-5 1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol 
• 1428475-61-9 (R)-benzyl (2-(cyclohex-1-en-1-yl)-2-(4-methoxyphenyl)ethyl)(methyl)carbamate 
• 868960-72-9 (S)-(1-oxaspiro[2.5]octan-2-yl)methanol 
• 108-94-1 cyclohexanone 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 129100-11-4 (S)-1-(1-Oxa-spiro[2.5]oct-2-yl)-methanol 
• 932-89-8 2-cyclohexylidene ethanol 
• 1552-92-7 ethyl cyclohexylideneacetate 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 1428475-60-8 (R)-benzyl (2-(cyclohex-1-en-1-yl)-2-(4-methoxyphenyl)ethyl)carbamate 
• 1428475-59-5 benzyl ((2R)-2-((1S)-2-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl)carbamate 
• 233257-09-5 (2S)-2-[(1R)-1-(4-methoxyphenyl)-2-nitroethyl]cyclohexanone 

Downstream Products

• 142761-11-3 (R)-4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol 
• 272788-00-8 C₁₇H₂₇NO₂*C₂₀H₁₈O₈ 
• 1049700-94-8 (-)-O-desmethylvenlafaxine hydrochloride 
• 142761-12-4 (S)-O-desmethylvenlafaxine 
• 1094598-39-6 R-venlafaxine N-oxide 
• 93413-45-7 (+)-Venlafaxine hydrochloride 
• 313471-76-0 R(-)-4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol fumarate hydrate salt 

Relevant articles and documents

Amino alcohols using the optically active amino alcohol derivative bi- Nord complex boron - -

Disclosed are an amino alcohol-boron-binol complex as an intermediate, including Complex 3-1-1 shown below, and a method for preparing an optically active amino alcohol by using the same, wherein a racemic amino alcohol is resolved in an enationselective manner using a boron compound and a (R)- or (S)-binol, whereby an amino alcohol derivative with high optical purity can be prepared at high yield.

Enantioseparation of chiral pharmaceuticals by vancomycin-bonded stationary phase and analysis of chiral recognition mechanism

The drug chirality is attracting increasing attention because of different biological activities, metabolic pathways, and toxicities of chiral enantiomers. The chiral separation has been a great challenge. Optimized high-performance liquid chromatography (HPLC) methods based on vancomycin chiral stationary phase (CSP) were developed for the enantioseparation of propranolol, atenolol, metoprolol, venlafaxine, fluoxetine, and amlodipine. The retention and enantioseparation properties of these analytes were investigated in the variety of mobile phase additives, flow rate, and column temperature. As a result, the optimal chromatographic condition was achieved using methanol as a main mobile phase with triethylamine (TEA) and glacial acetic acid (HOAc) added as modifiers in a volume ratio of 0.01% at a flow rate of 0.3?mL/minute and at a column temperature of 5°C. The thermodynamic parameters (eg, ΔH, ΔΔH, and ΔΔS) from linear van 't Hoff plots revealed that the retention of investigated pharmaceuticals on vancomycin CSP was an exothermic process. The nonlinear behavior of lnk′ against 1/T for propranolol, atenolol, and metoprolol suggested the presence of multiple binding mechanisms for these analytes on CSP with variation of temperature. The simulated interaction processes between vancomycin and pharmaceutical enantiomers using molecular docking technique and binding energy calculations indicated that the calculated magnitudes of steady combination energy (ΔG) coincided with experimental elution order for most of these enantiomers.

Application of Unusual Grignard Reaction for the Stereoselective Synthesis of Antidepressant Drug (R)-(-)-Venlafaxine

An enantioselective synthesis of antidepressant drug (R)-(-)-venlafaxine is accomplished as an application of recently explored unusual Grignard reaction. An innovative method for the generation of chirality at extremely reactive benzylic center along with determination of absolute stereochemistry has been discussed. The key steps involved in the synthesis include Sharpless asymmetric dihydroxylation for the induction of chirality and an unusual Grignard reaction.