Racephedrine
(−)-(1R,2S)-ephedrine (top), (+)-(1S,2R)-ephedrine (bottom) | |
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| Trade names | Efetonina; Ephoxamine |
| Other names | Racemic ephedrine; (±)-Ephedrine; dl-Ephedrine; (1RS,2SR)-Ephedrine |
| Drug class | Norepinephrine releasing agent; Sympathomimetic; Bronchodilator; Psychostimulant |
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| Chemical and physical data | |
| Formula | C10H15NO |
| Molar mass | 165.236 g·mol−1 |
| 3D model (JSmol) | |
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Racephedrine, also known as racemic ephedrine and sold under the brand names Efetonina and Ephoxamine among others, is the racemic form of ephedrine which has been used as a bronchodilator to treat asthma. More specifically, it is a racemic mixture of (1R,2S)- and (1S,2R)-enantiomers. Conversely, ephedrine is the enantiopure (1R,2S)-enantiomer. Racephedrine has been marketed for medical use in Italy. Like ephedrine, racephedrine is a releasing agent of norepinephrine and to a much lesser extent of dopamine. Both ephedrine enantiomers are active in this regard, but ephedrine ((1R,2S)-ephedrine) has greater potency than (1S,2R)-ephedrine.
| Compound | NE | DA | 5-HT | Ref | ||
|---|---|---|---|---|---|---|
| Dextroamphetamine (S(+)-amphetamine) | 6.6–7.2 | 5.8–24.8 | 698–1765 | |||
| S(–)-Cathinone | 12.4 | 18.5 | 2366 | |||
| Ephedrine ((–)-ephedrine; (1R,2S)-ephedrine) | 43.1–72.4 | 236–1350 | >10000 | |||
| (+)-Ephedrine ((1S,2R)-ephedrine) | 218 | 2104 | >10000 | |||
| Dextromethamphetamine (S(+)-methamphetamine) | 12.3–13.8 | 8.5–24.5 | 736–1291.7 | |||
| Levomethamphetamine (R(–)-methamphetamine) | 28.5 | 416 | 4640 | |||
| (+)-Phenylpropanolamine ((+)-norephedrine) | 42.1 | 302 | >10000 | |||
| (–)-Phenylpropanolamine ((–)-norephedrine) | 137 | 1371 | >10000 | |||
| Cathine ((+)-norpseudoephedrine) | 15.0 | 68.3 | >10000 | |||
| (–)-Norpseudoephedrine | 30.1 | 294 | >10000 | |||
| (–)-Pseudoephedrine | 4092 | 9125 | >10000 | |||
| Pseudoephedrine ((+)-pseudoephedrine) | 224 | 1988 | >10000 | |||
| The smaller the value, the more strongly the substance releases the neurotransmitter. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. | ||||||
Racephedrine has been used in a variety of combination drugs with other agents, including theophylline, aminophylline, oxtriphylline, phenobarbital, pentobarbital, pyrilamine, phenacetin, salicylamide, ascorbic acid, and opium, among others. Brand names of these combination preparations have included Amiphedrin, Amodrine, Amodrine E C, Asphamal-D, Asthmadrin, Cenamal, Cholarace, Phedrahist, Respirol, Salidin, Synate-M, and Synophedal.