9012. Synephrine

Nomenclature

CAS number: 94-07-5
4-Hydroxy-α-[(methylamino)methyl]benzenemethanol; p-hydroxy-α-[(methylamino)methyl]benzyl alcohol; 1-(4-hydroxyphenyl)-2-methylaminoethanol; p-methylaminoethanolphenol; β-methylamino-α-(4-hydroxyphenyl)ethyl alcohol; methylaminomethyl 4-hydroxyphenyl carbinol; Analeptin; Ethaphene; Oxedrine; Parasympatol; Simpalon; Synephrin (Neukonigsforder); Synthenate.
C9H13NO2; mol wt 167.21.
C 64.65%, H 7.84%, N 8.38%, O 19.14%.

Description and references

Prepd by hydrogenating ω-methylamino-4-hydroxyacetophenone in water in the presence of Pt or Pd: DE 566578 (1931 to Boehringer, Ing.), Frdl. 18, 3025.

Chemical structure

Properties

Crystals, mp 184-185°. Stable to air and light.

Derivative

Hydrochloride.

Nomenclature

CAS number: 5985-28-4
C9H13NO2.HCl; mol wt 203.67.
C 53.07%, H 6.93%, N 6.88%, O 15.71%, Cl 17.41%.

Properties

Crystals, mp 151-152°. Freely sol in water.

Derivative

Tartrate.

Nomenclature

CAS number: 16589-24-5
Corvasymton; Simpadren; Sympathol.
2C9H13NO2.C4H6O6; mol wt 484.50.
C 54.54%, H 6.66%, N 5.78%, O 33.02%.

Properties

Crystals, mp 188-190° (some dec). Freely sol in water; sol in alcohol.

Derivative

Tartaric acid monoester.

Nomenclature

CAS number: 6414-49-9
p-Methylaminoethanolphenol tartrate; Neupentedrin; Pentedrin.
C13H17NO7; mol wt 299.28.
C 52.17%, H 5.73%, N 4.68%, O 37.42%.

Therapeutic Category

Adrenergic; vasopressor.

Keywords

α-Adrenergic Agonist; Antihypotensive