4824. p-Hydroxyephedrine

Nomenclature

CAS number: 365-26-4
4-Hydroxy-α-[1-(methylamino)ethyl]benzenemethanol; p-hydroxy-α-[1-(methylamino)ethyl]benzyl alcohol; 1-(4-hydroxyphenyl)-2-methylaminopropanol; α-(1-methylaminoethyl)-p-hydroxybenzyl alcohol; oxyephedrin; Carnigen (Albert Roussel); Edornat (Albert-Roussel); Methylsympatol; Suprifen.
C10H15NO2; mol wt 181.23.
C 66.27%, H 8.34%, N 7.73%, O 17.66%.

Description and references

Prepn: Stolz, US 1878021 (1932 to Winthrop). Prepn of hydrochlorides of d- and l-forms: Takamatsu, Minaki, J. Pharm. Soc. Jpn. 76, 1230 (1956), C.A. 51, 4305e (1957).

Chemical structure

Properties

Cryst powder, mp 152-154°. Sparingly sol in water, alcohol, ether; readily sol in NaOH soln and dil acids.

Derivative

Hydrochloride.
C10H15NO2.HCl; mol wt 217.69.
C 55.17%, H 7.41%, N 6.43%, O 14.70%, Cl 16.29%.

Properties

Crystals, mp 209-211°. Sol in 3 parts water, 5 parts glycerol, 10 parts 90% alcohol. Sparingly sol in abs alcohol, acetone.

Derivative

d-Form hydrochloride.

Properties

Crystals, dec 223-224°. [α]D22 +33.8°.

Derivative

l-Form hydrochloride.

Properties

Crystals, dec 222-223°. [α]D22 35.5°.

Therapeutic Category

Adrenergic.