Racephedrine Explained
| Width: | 200px |
| Tradename: | Efetonina; Ephoxamine |
| Class: | Norepinephrine releasing agent
- Sympathomimetic; Bronchodilator; Psychostimulant
|
| Cas Number: | 90-81-3 |
| Pubchem: | 5032 |
| Drugbank: | DB14752 |
| Chemspiderid: | 4856 |
| Unii: | 03VRY66076 |
| Kegg: | C22822 |
| Chembl: | 279157 |
| Synonyms: | Racemic ephedrine; (±)-Ephedrine; dl-Ephedrine; (1RS,2SR)-Ephedrine |
| Iupac Name: | 2-(methylamino)-1-phenylpropan-1-ol |
| C: | 10 |
| H: | 15 |
| N: | 1 |
| O: | 1 |
| Smiles: | CC(C(C1=CC=CC=C1)O)NC |
| Stdinchi: | 1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3 |
| Stdinchikey: | KWGRBVOPPLSCSI-UHFFFAOYSA-N |
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.[1] [2] [3] [4] [5] 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.
Monoamine release by ephedrine and related agents (nM)[6] [7] | Compound | data-sort-type="number" | ! | data-sort-type="number" | ! | data-sort-type="number" | ! | Ref |
|---|
| Dextroamphetamine (S(+)-amphetamine) | 6.6–7.2 | 5.8–24.8 | 698–1765 | [8] [9] |
| 12.4 | 18.5 | 2366 | [10] |
| 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 | [11] |
| 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 | |
| 30.1 | 294 | >10000 | |
| 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.[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.
See also
Notes and References
- Book: Schweizerischer Apotheker-Verein . Index Nominum 2000: International Drug Directory . Medpharm Scientific Publishers . 2000 . 978-3-88763-075-1 . 30 August 2024 . 390.
- Web site: Racephedrine: Uses, Interactions, Mechanism of Action . DrugBank Online . 31 December 1995 . 30 August 2024.
- Web site: Racephedrine . PubChem . 30 August 2024.
- Tapay NJ . A racephedrine-phenyltoloxamine-containing compound (Ephoxamine) in the treatment of bronchial asthma . Curr Ther Res Clin Exp . 3 . 305–312 . July 1961 . 13775237 .
- Dubois de Montreynaud JM, Kochman S, Charreire J, Fondeville D, Houlon JP, Doco . [Delayed-action effect of a racephedrine, theophylline and phenobarbital combination on asthma. Study on 100 cases] . French . Therapie . 23 . 4 . 987–994 . 1968 . 5744603 .
- Rothman RB, Baumann MH . Monoamine transporters and psychostimulant drugs . Eur. J. Pharmacol. . 479 . 1–3 . 23–40 . 2003 . 14612135 . 10.1016/j.ejphar.2003.08.054.
- Rothman RB, Baumann MH . Therapeutic potential of monoamine transporter substrates . Curr Top Med Chem . 6 . 17 . 1845–1859 . 2006 . 17017961 . 10.2174/156802606778249766 .
- Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS . Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin . Synapse . 39 . 1 . 32–41 . January 2001 . 11071707 . 10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3 .
- Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW . Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products . Neuropsychopharmacology . 38 . 4 . 552–562 . 2013 . 23072836 . 3572453 . 10.1038/npp.2012.204 .
- Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA . In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates . J Pharmacol Exp Ther . 307 . 1 . 138–145 . October 2003 . 12954796 . 10.1124/jpet.103.053975 .
- Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV . The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue . Neuropsychopharmacology . 37 . 5 . 1192–203 . April 2012 . 22169943 . 3306880 . 10.1038/npp.2011.304 .
- Book: Project Label: Alphabetical Listing by Drug Product . Department of Justice, Drug Enforcement Administration, Office of Compliance and Regulatory Affairs, Regulatory Support Division, Information Systems Section . 1979 . 2024-08-31 . 235.
