Reboxetine

Base Information

• Chemical Name: Reboxetine
• CAS No.: 71620-89-8
• Deprecated CAS: 98769-81-4,98769-83-6,71621-36-8
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.397
• UNII: 947S0YZ36I
• DSSTox Substance ID: DTXSID1048257,DTXSID401315414
• Nikkaji Number: J569.655K
• Wikipedia: Reboxetine
• Wikidata: Q72506458
• NCI Thesaurus Code: C72838
• Pharos Ligand ID: C7VKFVTWLVPU
• ChEMBL ID: CHEMBL383921
• Mol file: 71620-89-8.mol

Synonyms:2-((2-ethoxyphenoxy)benzyl)morpholine methanesulfonate;reboxetine;reboxetine mesylate;Vestra

Chemical Property of Reboxetine

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 4.54E-08mmHg at 25°C
• Melting Point: 141-143oC
• Boiling Point: 443.7 °C at 760 mmHg
• PKA: 8.37±0.40(Predicted)
• Flash Point: 188.2 °C
• PSA: 39.72000
• Density: 1.113 g/cm³
• LogP: 3.52260
• Storage Temp.: Desiccate at +4°C
• Solubility.: Chloroform (Slightly), Water (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 313.16779360
• Heavy Atom Count: 23
• Complexity: 333

Purity/Quality:

97% ^*data from raw suppliers

Reboxetine, Mesylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC=CC=C1OC(C2CNCCO2)C3=CC=CC=C3
• Isomeric SMILES: CCOC1=CC=CC=C1O[C@@H]([C@H]2CNCCO2)C3=CC=CC=C3
• Recent ClinicalTrials: Efficacy of Reboxetine and Methylphenidate Treatment on Attentional, Sensory and Emotional Dysregulation in Adults With PTSD
• Recent EU Clinical Trials: The effect of various medications on emotioal processing, attention, experiences and sensory information processing
• General Description: Reboxetine mesylate (also known as Reboxetine or Reboxitine) is a selective norepinephrine reuptake inhibitor (NRI) with demonstrated efficacy in inhibiting the human norepinephrine transporter (hNET) while maintaining selectivity over serotonin (hSERT) and dopamine (hDAT) transporters. It exhibits potent activity in the low nanomolar range, comparable to other NRIs like atomoxetine, and has shown favorable pharmacokinetic properties and in vivo efficacy, suggesting its potential therapeutic utility in conditions linked to norepinephrine deficiency, such as acute and neuropathic pain.

Technology Process of Reboxetine

There total 108 articles about Reboxetine 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:

(2RS,3RS)-6-<α-(2-ethoxyphenoxy)benzyl>morpholin-3-one (93886-32-9,98769-79-0,98769-80-3,98819-75-1) → reboxetine (71620-89-8,71621-36-8,93851-86-6,98769-81-4,98769-83-6,98819-76-2,105017-38-7)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; for 4h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(01)96541-X

Reference yield:

trans-2,3-epoxy-3-phenylpropan-1-ol (40641-81-4) → reboxetine (71620-89-8,71621-36-8,93851-86-6,98769-81-4,98769-83-6,98819-76-2,105017-38-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) NaOH / 1.) H₂O, 70 deg C; 2.) H₂O, 70 deg C, 2.5 h

2: 61 percent / pyridine / 2 h / -10 °C

3: 84 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 - 5 °C

4: 2N NaOH / dioxane / 4 h / Ambient temperature

5: 32percent NH₄OH / methanol / 6 h / sealed flask

6: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / -10 - -5 °C

7: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature

8: RED-AL / toluene / 4 h / Ambient temperature

With ammonium hydroxide; sodium hydroxide; potassium tert-butylate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In 1,4-dioxane; pyridine; methanol; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)96541-X

Reference yield:

(2RS,3RS)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide (98769-72-3,98819-72-8) → reboxetine (71620-89-8,71621-36-8,93851-86-6,98769-81-4,98769-83-6,98819-76-2,105017-38-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 32percent NH₄OH / methanol / 6 h / sealed flask

2: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / -10 - -5 °C

3: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature

4: RED-AL / toluene / 4 h / Ambient temperature

With ammonium hydroxide; potassium tert-butylate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In methanol; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)96541-X

upstream raw materials:

(2RS,3RS)-6-<α-(2-ethoxyphenoxy)benzyl>morpholin-3-one

2-Ethoxyphenol

benzaldehyde

trans-2,3-epoxy-3-phenylpropan-1-ol

Downstream raw materials:

(S,S)-reboxetine

(2R,3R)-reboxetine

2S,3S-2-[α-(2-ethoxyphenoxy)benzyl]morpholine fumarate

(2S,3S)-2-[α-(2-ethoxyphenoxy)benzyl]morpholine succinate

Refernces

1- Or 3-(3-amino-2-hydroxy-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2- ones: Potent, selective, and orally efficacious norepinephrine reuptake inhibitors

10.1021/jm900888c

The research focuses on the development of potent, selective, and orally efficacious norepinephrine reuptake inhibitors (NRIs). The purpose of this study was to create a novel series of 1-(3-amino-2-hydroxy-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones that could selectively inhibit the human norepinephrine transporter (hNET) while demonstrating selectivity over the human serotonin (hSERT) and dopamine transporters (hDAT). The researchers synthesized and tested various compounds, leading to the discovery of several potent NRI candidates with low nanomolar hNET potency and excellent selectivity. Notably, compounds 20 and 22 showed similar potency to known NRI drugs like reboxetine and atomoxetine, along with good pharmacokinetic profiles and significant efficacy in reducing tail skin temperature in a telemetric rat model, suggesting potential for treating conditions associated with norepinephrine deficiency, including acute and neuropathic pain.

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