The Chinese plant 'Ma-Huang' contains this alkaloid, first isolated by Smith.
According to Read, the name 'Ma-Huang' is the name for various Ephedra species
but the material principally used in China is E. sinica Stapf. (Syn. E. j7ava
Porter Smith, E. Mahuang Liu). It has subsequently been discovered in European
species, notably E. helvetica C. A. Meyer and E. distachya Linn. The alkaloid
crystallizes in stout, colourless needles and has [α]D - 29.2° (MeOH). It yields
several crystalline salts and derivatives: hydrochloride, m.p. 188-9°C; [α]20D -
29.8° (H20); oxalate, m.p. 187°C; aurichloride, m.p. 128-9°C; picrate, m.p.
144°C and the methiodide, m.p. 212-3°C; [α]D - 21.8° (H20).
White crystals or adhering crystalline powder
adrenergic agonist, analeptic
Used in conjunction with LiAlH4 for chiral reductions
ChEBI: (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol is an alkylbenzene.
N-Methylephedrine has been recrystallised from Et2O, pet ether, of aqueous EtOH or aqueous MeOH and has been distilled under reduced pressure. [Smith J Chem Soc 2056 1927, Tanaka & Sugawa Yakugaku Zasshi (J Pharm Soc Japan) 72 1548 1952 (Chem Abstr 47 8682 1953), Takamatsu Yakugaku Zasshi (J Pharm Soc Japan) 76 1227 1956, Chem Abstr 51 4304 1957.] The hydrochloride has m 192-193o and [] D (c 5,H2O)[Prelog & Hüfliger Helv Chim Acta 33 2021 1950].20+30o [Beilstein 13 IV 1884.]
Smith., J. Chern. Soc., 2056 (1927)
Smith., ibid, 51 (1928)
Smith., ibid, 2755 (1929)
Wolfes., Arch. Pharrn., 268,327 (1930)
Preparation:
Nagai., J. Pharrn. Soc., Japan, No. 120, 109 (1892)
Nagai, Kanao., ibid, 48, 145 (1928)
