Midodrine

Base Information

• Chemical Name: Midodrine
• CAS No.: 42794-76-3
• Deprecated CAS: 97476-58-9
• Molecular Formula: C12H18 N2 O4
• Molecular Weight: 254.286
• Hs Code.: 2924299090
• European Community (EC) Number: 255-945-3,622-590-4
• UNII: 6YE7PBM15H
• DSSTox Substance ID: DTXSID0023321
• Nikkaji Number: J16.460G
• Wikipedia: Midodrine
• Wikidata: Q415051
• NCI Thesaurus Code: C61846
• RXCUI: 6963
• Pharos Ligand ID: 9URQLMFMXJ5X
• Metabolomics Workbench ID: 42615
• ChEMBL ID: CHEMBL1201212
• Mol file: 42794-76-3.mol

Synonyms:Amatine;Gutron;Midodrin;Midodrine;Midodrine Hydrochloride;Midodrine Monohydrochloride;Midon;Monohydrochloride, Midodrine;ProAmatine;ST 1085;ST-1085;ST1085

Chemical Property of Midodrine

Chemical Property:

• Boiling Point: 529.9±50.0 °C(Predicted)
• PKA: 13.47±0.20(Predicted)
• PSA: 93.81000
• Density: 1.204±0.06 g/cm3(Predicted)
• LogP: 0.90330
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 254.12665706
• Heavy Atom Count: 18
• Complexity: 263

Purity/Quality:

99% ^*data from raw suppliers

Midodrine >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)OC)C(CNC(=O)CN)O
• Recent ClinicalTrials: Treatment Strategy of Vasovagal Syncope
• Recent EU Clinical Trials: A Phase 4, Randomized-withdrawal, Double-blind, Placebo controlled, Parallel-group Study to Investigate the Clinical Benefit of Midodrine Hydrochloride in Male and Female Subjects with Symptomatic Orthostatic Hypotension
• Uses: Antihypotensive.

Technology Process of Midodrine

There total 4 articles about Midodrine 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: 75.0%

N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid (176851-43-7) → midodrine (42794-76-3,133163-25-4,133267-39-7,97476-58-9)

Guidance literature:

With hydrogenchloride; In methanol; water; at 20 ℃; for 2h; Schlenk technique; Inert atmosphere;

DOI:10.1021/ol400987p

Reference yield: 71.0%

2-dibenzylamino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide → midodrine (42794-76-3,133163-25-4,133267-39-7,97476-58-9)

Guidance literature:

With hydrogen; 5%-palladium/activated carbon; In ethanol; at 45 - 50 ℃; for 24h; under 3000.3 - 4500.45 Torr;

Reference yield:

1-(2',5'-dimethoxyphenyl)-2-aminoethanol hydrochloride (60407-53-6) → midodrine (42794-76-3,133163-25-4,133267-39-7,97476-58-9)

Guidance literature:

Multi-step reaction with 2 steps

1: diisopropylethylamine; HOBt_.H₂O; WSCDI / dimethylformamide / 12 h / 20 °C

2: HCl / dioxane / 2 h / 20 °C

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1124/jpet.106.102830

upstream raw materials:

N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid

1-(2',5'-dimethoxyphenyl)-2-aminoethanol hydrochloride

Downstream raw materials:

midodrine hydrochloride

Refernces

• 1、 Tsuda, Masahiro,Terada, Tomohiro,Irie, Megumi,Katsura, Toshiya,Niida, Ayumu,Tomita, Kenji,Fujii, Nobutaka,Inui, Ken-Ichi. "Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives". . p. 455 - 460. Retrieved 2008/01/27.