L-(-)-Ephedrine

Description

This alkaloid was first isolated by Kanao from the Chinese drug 'Ma-Huang' (Ephedra sinica Stapf.) and later by Wolfes from E. helvetica C. A. Meyer and E. distachya Linn. It forms a crystalline mass and has [α] ²⁰ _D - 14.56° (EtOH). Several crystalline salts and derivatives are known: the hydrochloride has m.p. 171-2°C; [α] ²⁰ _D- 33.27° (H20); the sulphate dihydrate, m.p. 285-6°C (dry, dec.); [α] ²⁸ _D- 31.99° (H20); the aurichloride, m.p. 188°C; platinichloride, m.p. 221°C (dec.); (-)-hydrogen tartrate, m.p. about 160° after sintering at 130°C; oxalate, m.p. 245°C (dec.) and the p-nitrobenzoyl derivative, m.p. 175-6°C; [α] ²⁸ _D- 49.58° (CHCI3).
The (+)-form has m.p. 52°C; [α] ²⁷ _D + 14.76° (EtOH), yielding a hydro_x0002_chloride, m.p. 171-2°C; [α] ²⁷ _D + 33.4° (EtOH); sulphate dihydrate, m.p. 285- 6°C (dry, dec.); [α] ²⁷ _D+ 31.51 0 C (H20); aurichloride, m.p. 188°C (dec.) and platinichloride, m.p. 221.5°C (dec.). The (±)-form crystallizes as colourless plates from Et20, m.p. 104-5°C and also furnishes a series of crystalline salts and derivatives.

Chemical properties

white powder

The Uses of L-(-)-Ephedrine

A metabolite of Phenmetrazine.

Definition

ChEBI: (-)-norephedrine is an amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1R,2S-stereoisomer). It is a plant alkaloid. It has a role as a plant metabolite. It is a member of amphetamines and a phenethylamine alkaloid.

Safety Profile

A human poison by ingestion. Poison experimentally by intravenous, subcutaneous, and intraperitoneal routes. Moderately toxic by an unspecified route. Human systemic effects by ingestion: sleep, increased pulse rate without blood pressure decrease, and chronic pulmonary edema or congestion, convulsions, headache, and blood pressure elevation. Used in production of drugs of abuse. When heated to decomposition it emits toxic fumes of NOx.

References

Kanao., Ber., 63,95 (1930) Wolfes., Arch. Pharrn., 268,87 (1930) Hey., J. Chern. Soc., 1232 (1930) Akabori, Momotani., J. Chern. Soc., Japan, 64, 608 (1943) Hoover, Hass., J. Org. Chern., 12,506 (1947)