Venlafaxine

Base Information

• Chemical Name: Venlafaxine
• CAS No.: 93413-69-5
• Molecular Formula: C17H27NO2
• Molecular Weight: 277.407
• Hs Code.: 2922509090
• Mol file: 93413-69-5.mol

Synonyms:Cyclohexanol,1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-, (?à)-;Trevilor;Velafax;Venlafaxin;Venlafaxine;Venlafaxine XR;Venlafexine;

Chemical Property of Venlafaxine

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 1.14E-07mmHg at 25°C
• Melting Point: 72-74 °C
• Refractive Index: 1.579
• Boiling Point: 397.6 °C at 760 mmHg
• PKA: pKa 9.5 (Uncertain)
• Flash Point: 194.2 °C
• PSA: 32.70000
• Density: 1.06 g/cm³
• LogP: 3.03560
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Water Solubility.: <0.1g/L(room temperature)

Purity/Quality:

99% up, ^*data from raw suppliers

D,L-Venlafaxine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A optically active version of Venlafaxine, a selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant antidepressant;serotonin-norepinephrine reuptake inhibitor A selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant.
• Biological Functions: Venlafaxine (Effexor) inhibits the reuptake of both serotonin and norepinephrine at their respective presynaptic sites.This drug does not have significant effects at muscarinic, histamine, or α-adrenergic receptors and therefore is devoid of many of the side effects associated with the TCAs.Venlafaxine and its active metabolite O-desmethyl-venlafaxine, have half lives of 5 and 11 hours respectively, so dosing twice a day is necessary. However, an extended release preparation (Effexor XR) now allows for once-daily dosing and better tolerance. Venlafaxine has a side effect profile similar to that of the SSRIs. Higher doses of venlafaxine result in modest increases in blood pressure in approximately 5% of patients.Venlafaxine has minimal effects on the cytochrome P450 enzyme system.
• Clinical Use: Venlafaxine is a methoxyphenylethylamine antidepressant that resembles an open TCA with one of the aromatic rings replaced by a cyclohexanol ring and a dimethylaminomethyl group rather than a dimethylaminopropyl chain.
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: increased risk of bleeding with aspirin and NSAIDs; possibly increased serotonergic effects with tramadol. Anti-arrhythmics: risk of ventricular arrhythmias with amiodarone - avoid. Antibacterials: risk of ventricular arrhythmias with erythromycin, moxifloxacin - avoid. Anticoagulants: effects of warfarin possibly enhanced; possibly increased risk of bleeding with dabigatran. Antidepressants: avoid with MAOIs and moclobemide (increased risk of toxicity); possibly enhanced serotonergic effects with duloxetine, mirtazapine and St John’s wort; possible increased risk of convulsions with vortioxetine - avoid. Antimalarials: avoid concomitant use with artemether/lumefantrine and piperaquine with artenimol. Antipsychotics: increases concentration of clozapine and haloperidol. Beta-blockers: risk of ventricular arrhythmias with sotalol - avoid. Dapoxetine: possible increased risk of serotonergic effects - avoid. Dopaminergics: use entacapone with caution; increased risk of hypertension and CNS excitation with selegiline - avoid concomitant use. Methylthioninium: risk of CNS toxicity - avoid if possible.

Technology Process of Venlafaxine

There total 107 articles about Venlafaxine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.9%

venlafaxine hydrochloride (99300-78-4) → 1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol (93413-69-5)

Guidance literature:

With sodium hydroxide; In water;

DOI:10.1002/chir.22790

Reference yield: 98.0%

N,N-didesmethylvenlafaxine (93413-77-5,272788-06-4,273720-73-3,149289-31-6) → 1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol (93413-69-5)

Guidance literature:

With sodium hydroxide; formaldehyd; formic acid; In water;

Reference yield: 93.8%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1-[cyano(4-methoxyphenyl)methyl]cyclohexanol (93413-76-4,131801-69-9) → 1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol (93413-69-5)

Guidance literature:

formaldehyd; 1-[cyano(4-methoxyphenyl)methyl]cyclohexanol; With hydrogen; acetic acid; 5%-palladium/activated carbon; In water; at 5 - 60 ℃; under 9000.9 Torr;

With sodium hydroxide; water; In toluene; at 10 ℃; pH=6.3;

upstream raw materials:

formaldehyd

N,N-didesmethylvenlafaxine

5-(4-methoxyphenyl)-3-aza-1-oxaspiro[5,5]undecane

1-[cyano(4-methoxyphenyl)methyl]cyclohexanol

Downstream raw materials:

(S)-1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)cyclohexanol

(R)-1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol

venlafaxine hydrochloride

(R)-4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol

Refernces

• 1、 An, Yi,Chen, Fener,Li, Weijian,Li, Yaling,Tang, Pei,Wang, Zhenzhen,Wu, Mengjuan,Xue, Yansong. "The total synthesis of (-) -strempeliopine: Via palladium-catalyzed decarboxylative asymmetric allylic alkylation". . p. 1402 - 1405. Retrieved 2022/02/09.
• 2、 -. "Amino alcohols using the optically active amino alcohol derivative bi- Nord complex boron - -". Paragraph 0064; 0071-0076; 0281-0283; 0285-0286. . Retrieved 2021/04/16.