6068. N-Methylephedrine
Nomenclature
CAS number: 552-79-4
α-[1-(Dimethylamino)ethyl]benzenemethanol; erythro-α-[1-(dimethylamino)ethyl]benzyl alcohol; 2-dimethylamino-1-phenylpropanol; N,N-dimethylnorephedrine. C11H17NO; mol wt 179.26.
C 73.70%, H 9.56%, N 7.81%, O 8.93%.
Description and references
Isoln of l-form from Ephedra distachya L. (E. vulgaris Rich.), and allied Gnetaceae: Smith, J. Chem. Soc. 1927, 2056; Wolfes, Arch. Pharm. 268, 327 (1930). Prepn of l-form: Smith, loc. cit.; of d-, l-, and dl-forms, and resolution of racemic mixture: Nagai, Kanao, Ann. 470, 157 (1929); of dl-form: Pfanz, Müller, Arch. Pharm. 288, 11 (1955).
Derivative
dl-Form.Properties
Crystals from petr ether or methanol, mp 63.5-64.5°. Readily sol in the usual solvents.Derivative
dl-Form hydrochloride.Nomenclature
Metheph (Napp).Properties
Crystals from acetone, mp 207-208°.Derivative
d-Form.Properties
Crystals, mp 87-87.5°. [α]D20 +29.2° (c = 4 in methanol).Derivative
d-Form hydrochloride.Properties
Crystals from ethyl acetate, mp 192°. [α]D20 +30.1°.Derivative
l-Form.Properties
Crystals from petr ether, mp 87-88°. [α]D 29.5° (c = 4.5 in methanol).Derivative
l-Form hydrochloride.Properties
Crystals from ethyl acetate or alcohol, mp 192°. [α]D20 29.8° (c = 4.6). Readily sol in water; less sol in alcohol; sparingly sol in acetone.Derivative
β-Camphorsulfonate.Nomenclature
N-Methylephedrine camsylate; Tybraine (Nicholas).Therapeutic Category
Analeptic.
Keywords
Bronchodilator; Ephedrine Derivatives