Chemistry:Racephedrine
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.[3] Conversely, ephedrine is the enantiopure (1R,2S)-enantiomer.[1] Racephedrine has been marketed for medical use in Italy.[1] Like ephedrine, racephedrine is a releasing agent of norepinephrine and to a much lesser extent of dopamine.[6][7][8][9] Both ephedrine enantiomers are active in this regard, but ephedrine ((1R,2S)-ephedrine) has greater potency than (1S,2R)-ephedrine.[6][7][8][9]
| Compound | NE | DA | 5-HT | 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 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.[12]
See also
References
- ↑ 1.0 1.1 1.2 Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 390. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA390. Retrieved 30 August 2024.
- ↑ "Racephedrine: Uses, Interactions, Mechanism of Action". 31 December 1995. https://go.drugbank.com/drugs/DB14752.
- ↑ 3.0 3.1 "Racephedrine". https://pubchem.ncbi.nlm.nih.gov/compound/5032.
- ↑ "A racephedrine-phenyltoloxamine-containing compound (Ephoxamine) in the treatment of bronchial asthma". Curr Ther Res Clin Exp 3: 305–312. July 1961. PMID 13775237.
- ↑ "[Delayed-action effect of a racephedrine, theophylline and phenobarbital combination on asthma. Study on 100 cases]" (in French). Therapie 23 (4): 987–994. 1968. PMID 5744603.
- ↑ 6.0 6.1 Cite error: Invalid
<ref>tag; no text was provided for refs namedRothmanBaumann2003 - ↑ 7.0 7.1 Cite error: Invalid
<ref>tag; no text was provided for refs namedRothmanBaumann2006 - ↑ 8.0 8.1 8.2 8.3 8.4 8.5 8.6 "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse 39 (1): 32–41. January 2001. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707.
- ↑ 9.00 9.01 9.02 9.03 9.04 9.05 9.06 9.07 9.08 9.09 "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. doi:10.1124/jpet.103.053975. PMID 12954796.
- ↑ "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology 38 (4): 552–562. 2013. doi:10.1038/npp.2012.204. PMID 23072836.
- ↑ "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology 37 (5): 1192–203. April 2012. doi:10.1038/npp.2011.304. PMID 22169943.
- ↑ 12.0 12.1 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. p. 235. https://books.google.com/books?id=8HJc_WTwdNsC&pg=PT235. Retrieved 2024-08-31.
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