 (−)-(1R,2S)-ephedrine (top), (+)-(1S,2R)-ephedrine (bottom) | |
| Clinical data | |
|---|---|
| Trade names | Efetonina; Ephoxamine |
| Other names | Racemic ephedrine; (±)-Ephedrine;dl-Ephedrine; (1RS,2SR)-Ephedrine |
| Drug class | Norepinephrine releasing agent;Sympathomimetic;Bronchodilator;Psychostimulant |
| Identifiers | |
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| CAS Number | |
| PubChemCID | |
| DrugBank | |
| ChemSpider | |
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| KEGG | |
| ChEMBL | |
| Chemical and physical data | |
| Formula | C10H15NO |
| Molar mass | 165.236 g·mol−1 |
| 3D model (JSmol) | |
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Racephedrine, also known asracemic ephedrine and sold under the brand namesEfetonina andEphoxamine among others, is theracemic form ofephedrine which has been used as abronchodilator to treatasthma.[1][2][3][4][5] More specifically, it is a racemic mixture of (1R,2S)- and (1S,2R)-enantiomers.[3] Conversely, ephedrine is theenantiopure (1R,2S)-enantiomer.[1] Racephedrine has been marketed for medical use inItaly.[1] Like ephedrine, racephedrine is areleasing agent ofnorepinephrine and to a much lesser extent ofdopamine.[6][7][8][9] Both ephedrine enantiomers are active in this regard, but ephedrine ((1R,2S)-ephedrine) has greaterpotency than (1S,2R)-ephedrine.[6][7][8][9]
| Compound | NETooltip Norepinephrine | DATooltip Dopamine | 5-HTTooltip Serotonin | Ref | ||
|---|---|---|---|---|---|---|
| Dextroamphetamine (S(+)-amphetamine) | 6.6–7.2 | 5.8–24.8 | 698–1765 | [8][10] | ||
| S(–)-Cathinone | 12.4 | 18.5 | 2366 | [9] | ||
| Ephedrine ((–)-ephedrine; (1R,2S)-ephedrine) | 43.1–72.4 | 236–1350 | >10000 | [8] | ||
| (+)-Ephedrine ((1S,2R)-ephedrine) | 218 | 2104 | >10000 | [8][9] | ||
| Dextromethamphetamine (S(+)-methamphetamine) | 12.3–13.8 | 8.5–24.5 | 736–1291.7 | [8][11] | ||
| Levomethamphetamine (R(–)-methamphetamine) | 28.5 | 416 | 4640 | [8] | ||
| (+)-Phenylpropanolamine ((+)-norephedrine) | 42.1 | 302 | >10000 | [9] | ||
| (–)-Phenylpropanolamine ((–)-norephedrine) | 137 | 1371 | >10000 | [9] | ||
| Cathine ((+)-norpseudoephedrine) | 15.0 | 68.3 | >10000 | [9] | ||
| (–)-Norpseudoephedrine | 30.1 | 294 | >10000 | [9] | ||
| (–)-Pseudoephedrine | 4092 | 9125 | >10000 | [9] | ||
| Pseudoephedrine ((+)-pseudoephedrine) | 224 | 1988 | >10000 | [9] | ||
| The smaller the value, the more strongly the substance releases the neurotransmitter. See alsoMonoamine releasing agent § Activity profiles for a larger table with more compounds. | ||||||
Racephedrine has been used in a variety ofcombination drugs with other agents, includingtheophylline,aminophylline,oxtriphylline,phenobarbital,pentobarbital,pyrilamine,phenacetin,salicylamide,ascorbic acid, andopium, among others.[12] 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.[12]