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

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

Uses

Used in Pharmaceutical Industry:
S-Venlafaxine is used as an antidepressant for the treatment of major depressive disorder, generalized anxiety disorder, social anxiety disorder, and panic disorder. It works by selectively inhibiting the reuptake of serotonin and noradrenaline in the brain, thereby increasing their levels and improving mood, anxiety, and other related symptoms.
S-Venlafaxine is used as a more potent and safer alternative to the racemic mixture of Venlafaxine, as it has been found to have fewer side effects and a better tolerability profile. This makes it a preferred choice for patients who may be sensitive to the side effects of the racemic mixture or who require a more targeted treatment approach.
In addition to its primary use as an antidepressant, S-Venlafaxine may also have potential applications in other areas of mental health treatment, such as the management of chronic pain, fibromyalgia, and other conditions where the modulation of serotonin and noradrenaline levels may be beneficial. However, further research is needed to fully explore these potential applications and establish their efficacy and safety.

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

• 1428475-59-5 benzyl ((2R)-2-((1S)-2-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl)carbamate 
• 1428475-60-8 (R)-benzyl (2-(cyclohex-1-en-1-yl)-2-(4-methoxyphenyl)ethyl)carbamate 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 1552-92-7 ethyl cyclohexylideneacetate 
• 932-89-8 2-cyclohexylidene ethanol 
• 129100-11-4 (S)-1-(1-Oxa-spiro[2.5]oct-2-yl)-methanol 
• 124-40-3 dimethyl amine 
• 50415-68-4 methyl 2-(4-methoxyphenyl)prop-2-enoate 
• 93413-69-5 1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol 
• 272788-00-8 (R)-venlafaxine-di-p-toluoyl-D-tartrate salt 
• 1428475-61-9 (R)-benzyl (2-(cyclohex-1-en-1-yl)-2-(4-methoxyphenyl)ethyl)(methyl)carbamate 

Downstream Products

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

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.

Bisguanidinium-Catalyzed Epoxidation of Allylic and Homoallylic Amines under Phase Transfer Conditions

A highly enantioselective epoxidation reaction of allylic and homoallylic amines has been disclosed using an ion pair catalyst, which consists of chiral cationic bisguanidinium [BG]2+ and an achiral tetraperoxyditungstate anion [W2O2(μ-O)(O2)4]2-. The terminal oxidant is a stoichiometric amount of aqueous hydrogen peroxide, an environmentally benign reagent. Up to 96% enantiomeric excess and 99% yields were achieved for 1,1′-disubstituted and 1,2-disubstituted allylic protected amines and 1,2-disubstituted homoallylic protected amines. The identity of the ion pair catalyst was uncovered using X-ray crystallography and revealed that the achiral tetraperoxyditungstate anion species [W2O2(μ-O)(O2)4]2- is nudged nicely into the central cavity of the chiral dication. The ion pair catalyst was also characterized using infrared (IR) and Raman spectroscopies. The synthesis of (-)-venlafaxine was achieved via this reported methodology to demonstrate its usefulness.

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.

Efficient resolution of venlafaxine and mechanism study via X-ray crystallography

Numbers of resolving factors were investigated to improve resolution of venlafaxine 1. An effective resolving agent, O,O′-di-p-toluoyl-(R, R)-tartaric acid 2, was screened using similar method of ‘Dutch resolution’ from tartaric acid derivatives. The resolution efficiency was up to 88.4%, when the ratio of rac-1 and 2 was 1:0.8 in THF with little water (10:1?v/v). Enantiomerically pure venlafaxine was prepared with 99.1% ee in 82.2% yield. The chiral resolution mechanism was first explained through X-ray crystallographic study. One diastereomeric salt with well solubility forms a columnar supramolecular structure as the acidic salt (R)-1·2, while the other diastereomeric salt with less solubility forms a multilayered sandwich supramolecular structure by enantio-differentiation self-assembly as the neutral salt 2(S)-1·2. The water molecules play a key role in the optical resolution, as indicated by the special structures of the diastereomeric salts.

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.

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.

ASYMMETRIC SYNTHESIS OF (-)-VENLAFAXINE USING ORGANOCATALYST

The patent discloses an asymmetric synthesis of (?)-venlafaxine using an organocatalyst via a unified strategy employing organcatalytic Michael addition, regio-selective dehydration and selective epoxide ring opening.

NOVEL PROCESS FOR TOTAL SYNTHESIS OF VENLAFAXINE

There is a need for short, resolution free asymmetric process for synthesis of one isomer of venlafaxine, (-)-venlafaxine. The invention provides a novel, short process of synthesis of (-)-venlafaxine, with yield greater than 50% and ee> 99%. This process can be used for racemic synthesis of venlafaxine with overall yield 65%.

ASYMMETRIC SYNTHESIS OF (-)-VENLAFAXINE USING ORGANOCATALYST

The patent discloses an asymmetric synthesis of (-)-venlafaxine using an organocatalyst via a unified strategy employing organcatalytic Michael addition, regio-selective dehydration and selective epoxide ring opening.

A protecting group free and scalable approach towards total synthesis of (-)-venlafaxine

A protecting group free asymmetric total synthesis of (-)-venlafaxine is reported. The strategy employs Sharpless epoxidation and regio-selective epoxide ring opening by an in situ generated Gilman reagent as key steps. This paper reports a 53% overall yield in 6 steps for total synthesis of (-)-venlafaxine. This journal is the Partner Organisations 2014.