2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide monohydrochloride

Description

2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide monohydrochloride · CAS 3092-17-9 · C12H18N2O4. UNII 6YE7PBM15H. Melting Point: 200; Melting Point: 150 °C; Melting Point: 200 - 203 °C.

Identification

Computed Descriptors

Physical & Chemical Properties

Physical description & handling notes

• Solid
• Soluble
• Specific optical rotation = +138.5 deg at 20 °C/D (concentration = 0.5 in chloroform)
• When heated to decomposition, material emits toxic fumes of nitrogen oxides and hydrogen chloride.
• pKa = 7.8 (0.3% aqueous solution); pH 3.5 to 5.5 (5% aqueous solution) /Midodrine hydrochloirde/
• 159.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID1047493]

GHS Hazard Classification

Documented Uses

• Use (kg; approx.) in Germany (2009): >10
• Consumption (g per capita; approx.) in Germany (2009): 0.000122
• Synthesized from hydroquinone dimethyl ether by Friedel-Crafts acylation with chloroacetyl chloride, amination to the corresponding 2-aminoacetophenone, acylation at the amino function with chloroacetyl chloride, displacement of the chloro by the azido group and finally reduction with, e.g., sodium borohydride and catalytic hydrogenation (Pd/C).
• For the treatment of symptomatic orthostatic hypotension (OH).
• FDA proposed to withdraw approval of the drug midodrine hydrochloride, used to treat the low blood pressure condition, orthostatic hypotension, because required post-approval studies that verify the clinical benefit of the drug have not been done. To date, neither the original manufacturer nor any generic manufacturer has demonstrated the drug's clinical benefit, for example, by showing that use of the drug improved a patient's ability to perform life activities.
• ...used as a vasoconstrictor agent in the treatment of hypotension

Synonyms

midodrine; 42794-76-3; Midodrin; Midodrina; Midodrinum; Midodrinum [INN-Latin]; St 1085; ST-1085; 1-(2',5'-Dimethoxyphenyl)-2-glycinamidoethanol; DL-N1-(beta-Hydroxy-2,5-dimethoxyphenethyl)glycinamid; 6YE7PBM15H; Acetamide, 2-amino-N-(2-(2,5-dimethoxyphenyl)-2-hydroxyethyl)-; 2-Amino-N-(2,5-dimethoxy-beta-hydroxyphenethyl)acetamid; 2-Amino-N-(2,5-dimethoxy-beta-hydroxyphenethylacetamide; 2-Amino-N-(2,5-dimethoxy-beta-hydroxyphenethyl)acetamide; CHEBI:6933

Frequently Asked Questions

What are the CAS number and molecular formula of 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide monohydrochloride?

CAS 3092-17-9; molecular formula C12H18N2O4; molecular weight — g/mol.

What other names is 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide monohydrochloride known by?

midodrine, 42794-76-3, Midodrin, Midodrina, Midodrinum, Midodrinum [INN-Latin].

Is 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide monohydrochloride classified as hazardous?

Hazard statements reported: H301.

What are the key physical properties of 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide monohydrochloride?

Melting Point: 200; Melting Point: 150 °C; Melting Point: 200 - 203 °C; Solubility: 4.45e+00 g/L.

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.