Etilefrine

Base Information

• Chemical Name: Etilefrine
• CAS No.: 709-55-7
• Deprecated CAS: 10128-36-6
• Molecular Formula: C10H15 N O2
• Molecular Weight: 181.235
• Hs Code.: 2922509090
• European Community (EC) Number: 211-910-4
• UNII: ZB6F8MY53V
• DSSTox Substance ID: DTXSID1023029
• Nikkaji Number: J6.942F
• Wikipedia: Etilefrine
• Wikidata: Q417873
• NCI Thesaurus Code: C65576
• Pharos Ligand ID: L8X6QAHABAQ5
• Metabolomics Workbench ID: 143594
• ChEMBL ID: CHEMBL86882
• Mol file: 709-55-7.mol

Synonyms:Adrenam;Adrianol, Ethyl;Bioflutin;Cardanat;Circupon;Effortil;Efortil;Ethyl Adrianol;Ethyladrianol;Ethylnorphenylephrine;Ethylphenylephrine;Eti Puren;Eti-Puren;etil von ct;Etilefrin;Etilefrin AL;Etilefrin ratiopharm;Etilefrin-ratiopharm;Etilefrine;Etilefrine Hydrochloride;Etilefrine Pivalate Hydrochloride;Fetanol;Hydrochloride, Etilefrine;Hydrochloride, Etilefrine Pivalate;Phetanol;Pivalate Hydrochloride, Etilefrine;Thomasin

Chemical Property of Etilefrine

Chemical Property:

• Melting Point: 147-148°
• Refractive Index: 1.5464 (estimate)
• Boiling Point: 314.35°C (rough estimate)
• PKA: 9.81±0.10(Predicted)
• Flash Point: 155.5oC
• PSA: 52.49000
• Density: 1.0918 (rough estimate)
• LogP: 1.42600
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 181.110278721
• Heavy Atom Count: 13
• Complexity: 141

Purity/Quality:

99.9% ^*data from raw suppliers

ETILEFRINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNCC(C1=CC(=CC=C1)O)O
• Recent ClinicalTrials: Effects of Adding Hypertonic Saline Solutions and/or Etilefrine to Standard Diuretics Therapy in Hepatic Ascites
• Recent EU Clinical Trials: Validation of the efficiency of repurposed drugs on the basis of their cellular transcriptomic signature, antagonist to that of the influenza A infection.
• Recent NIPH Clinical Trials: The effect of ephedrine and etilefrine on systolic pressure variation and pulse pressure variation
• Uses: Etilefrin is a sympathomimetic drug that increases the pulse rate, cardiac output, stroke volume, central venous pressure and mean arterial pressure of healthy individuals. Etilefrin has both beta 1 and alpha adrenergic effects on humans and is mainly used for the treatment of patients with orthostatic hypotension. ETILEFRINE-D5 is a sympathomimetic drug that increases the pulse rate, cardiac output, stroke volume, central venous pressure and mean arterial pressure of healthy individuals. Etilefrin has both beta 1 and alpha adrenergic effects on humans and is mainly used for the treatment of patients with orthostatic hypotension.
• Therapeutic Function: Tranquilizer

Technology Process of Etilefrine

There total 8 articles about Etilefrine 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: 54.0%

norfenefrine (536-21-0) + acetaldehyde (75-07-0,9002-91-9) → etilefrine (709-55-7,95585-90-3) + 3-(2-(diethylamino)-1-hydroxyethyl)phenol

Guidance literature:

norfenefrine; acetaldehyde; In ethanol; at 20 ℃; for 2h;

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 1h; chemoselective reaction;

DOI:10.1039/c8gc03823f

Reference yield:

3-hydroxystyrene (620-18-8,24979-69-9) → etilefrine (709-55-7,95585-90-3) + 3-(2-(diethylamino)-1-hydroxyethyl)phenol

Guidance literature:

Multi-step reaction with 2 steps

1.1: iron(II) phthalocyanine; O-pivaloylhydroxylamine trifluoromethanesulfonate salt / acetonitrile; water / 16 h / 20 °C

2.1: ethanol / 2 h / 20 °C

2.2: 1 h / 0 °C

With iron(II) phthalocyanine; O-pivaloylhydroxylamine trifluoromethanesulfonate salt; In ethanol; water; acetonitrile;

DOI:10.1039/c8gc03823f

Reference yield:

meta-hydroxybenzaldehyde (100-83-4) → etilefrine (709-55-7,95585-90-3) + 3-(2-(diethylamino)-1-hydroxyethyl)phenol

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C / Inert atmosphere; Schlenk technique

1.2: 16 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

2.1: iron(II) phthalocyanine; O-pivaloylhydroxylamine trifluoromethanesulfonate salt / acetonitrile; water / 16 h / 20 °C

3.1: ethanol / 2 h / 20 °C

3.2: 1 h / 0 °C

With n-butyllithium; iron(II) phthalocyanine; O-pivaloylhydroxylamine trifluoromethanesulfonate salt; In tetrahydrofuran; ethanol; hexane; water; acetonitrile; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination;

DOI:10.1039/c8gc03823f

upstream raw materials:

2-ethylamino-1-(3-hydroxy-phenyl)-ethanone

2-bromo-3-acetyloxylacetophenone

norfenefrine

acetaldehyde

Downstream raw materials:

(R)-N-ethylnorphenylephrine

(S)-etilefrine

C-((S)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-N-ethyl-N-[2-hydroxy-2-(3-hydroxy-phenyl)-ethyl]-methanesulfonamide

3-hydroxyphenylacetaldehyde

Refernces

• 1、 -. "Pharmaceutical formula". . . Retrieved 2008/06/13.