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

Public-database records for 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide monohydrochloride (CAS 3092-17-9), reproduced here for independent cross-checking.

Safety classification and hazard statements

Physical description and 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]

Reported physical properties

How this substance is indexed

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

Names this substance appears under

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

Computed molecular descriptors

Database abstract

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

Source: PubChem / Wikidata; the batch COA governs where values differ.