42794-76-3

Basic information

• Product Name: MIDODRINE
• Synonyms: MIDODRINE;Acetamide, 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]- (9CI);2-Amino-N-(2,5-dimethoxy-β-hydroxyphenethyl)acetamide
• CAS NO: 42794-76-3
• Molecular Formula: C₁₂H₁₈N₂O₄
• Molecular Weight: 254.28
• EINECS: 255-945-3
• Mol File: 42794-76-3.mol

Chemical Properties

• Boiling Point: 529.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.204±0.06 g/cm3(Predicted)
• PKA: 13.47±0.20(Predicted)
• CAS DataBase Reference: MIDODRINE(CAS DataBase Reference)
• NIST Chemistry Reference: MIDODRINE(42794-76-3)
• EPA Substance Registry System: MIDODRINE(42794-76-3)

Safety Data

• Hazardous Substances Data: 42794-76-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
MIDODRINE is used as an antihypotensive agent for the treatment of certain hypotensive states. It functions as a peripheral vasoconstrictor, helping to increase blood pressure and improve blood flow in individuals suffering from low blood pressure conditions.
Used in Medical Treatment:
MIDODRINE is used as a therapeutic agent in the management of orthostatic hypotension, a condition where blood pressure drops significantly upon standing. It helps to alleviate symptoms such as dizziness, lightheadedness, and fatigue associated with this condition.
Used in Clinical Settings:
MIDODRINE is utilized in clinical settings to treat patients with symptomatic neurogenic orthostatic hypotension, a condition that results from the dysfunction of the autonomic nervous system. It helps to improve the patient's quality of life by reducing the severity of symptoms and enhancing their ability to perform daily activities.

InChI:InChI=1/C12H18N2O4/c1-17-8-3-4-11(18-2)9(5-8)10(15)7-14-12(16)6-13/h3-5,10,15H,6-7,13H2,1-2H3,(H,14,16)

Upstream product

• 176851-43-7 N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid 
• 60407-53-6 1-(2',5'-dimethoxyphenyl)-2-aminoethanol hydrochloride 

Downstream Products

• 133163-28-7 midodrine hydrochloride 

Relevant articles and documents

Organobase-catalyzed amidation of esters with amino alcohols

A base-mediated procedure for the amidation of unactivated esters with amino alcohols is reported. Optimization and exemplification of the catalytic process are described, furnishing products in 40-100% isolated yield.

Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives

Midodrine is an oral drug for orthostatic hypotension. This drug is almost completely absorbed after oral administration and converted into its active form, 1-(2′,5′-dimethoxyphenyl)-2-aminoethanol) (DMAE), by the cleavage of a glycine residue. The intestinal H+-coupled peptide transporter 1 (PEPT1) transports various peptide-like drugs and has been used as a target molecule for improving the intestinal absorption of poorly absorbed drugs through amino acid modifications. Because midodrine meets these requirements, we examined whether midodrine can be a substrate for PEPT1. The uptake of midodrine, but not DMAE, was markedly increased in PEPT1-expressing oocytes compared with water-injected oocytes. Midodrine uptake by Caco-2 cells was saturable and was inhibited by various PEPT1 substrates. Midodrine absorption from the rat intestine was very rapid and was significantly inhibited by the high-affinity PEPT1 substrate cyclacillin, assessed by the alteration of the area under the blood concentration-time curve for 30 min and the maximal concentration. Some amino acid derivatives of DMAE were transported by PEPT1, and their transport was dependent on the amino acids modified. In contrast to neutral substrates, cationic midodrine was taken up extensively at alkaline pH, and this pH profile was reproduced by a 14-state model of PEPT1, which we recently reported. These findings indicate that PEPT1 can transport midodrine and contributes to the high bioavailability of this drug and that Gly modification of DMAE is desirable for a prodrug of DMAE. Copyright

A process for the preparation of midodrine

The invention provides a process for the preparation of 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide of the formula 1 by hydrogenolysis of substituted 2-dibenzylamino-N-[2-(2',5'-dimethoxyphenyl)-2-hydroxy-ethyl]acetamide having the formula (5), wherein Ar and Ar' are aryl groups.