Racephedrine

Racephedrine
(−)-(1R,2S)-ephedrine (top),
(+)-(1S,2R)-ephedrine (bottom)
Clinical data
Trade namesEfetonina; Ephoxamine
Other namesRacemic ephedrine; (±)-Ephedrine; dl-Ephedrine; (1RS,2SR)-Ephedrine
Drug classNorepinephrine releasing agent; Sympathomimetic; Bronchodilator; Psychostimulant
Identifiers
  • 2-(methylamino)-1-phenylpropan-1-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC10H15NO
Molar mass165.236 g·mol−1
3D model (JSmol)
  • CC(C(C1=CC=CC=C1)O)NC
  • InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3
  • Key: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.[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]

Monoamine release by ephedrine and related agents (EC50Tooltip half maximal effective concentration, nM)[6][7]
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 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]

  1. ^ a b c Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 390. ISBN 978-3-88763-075-1. Retrieved 30 August 2024.
  2. ^ "Racephedrine: Uses, Interactions, Mechanism of Action". DrugBank Online. 31 December 1995. Retrieved 30 August 2024.
  3. ^ a b "Racephedrine". PubChem. Retrieved 30 August 2024.
  4. ^ Tapay NJ (July 1961). "A racephedrine-phenyltoloxamine-containing compound (Ephoxamine) in the treatment of bronchial asthma". Curr Ther Res Clin Exp. 3: 305–312. PMID 13775237.
  5. ^ Dubois de Montreynaud JM, Kochman S, Charreire J, Fondeville D, Houlon JP, Doco (1968). "[Delayed-action effect of a racephedrine, theophylline and phenobarbital combination on asthma. Study on 100 cases]". Therapie (in French). 23 (4): 987–994. PMID 5744603.
  6. ^ a b c Rothman RB, Baumann MH (2003). "Monoamine transporters and psychostimulant drugs". Eur. J. Pharmacol. 479 (1–3): 23–40. doi:10.1016/j.ejphar.2003.08.054. PMID 14612135.
  7. ^ a b c Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Curr Top Med Chem. 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961.
  8. ^ a b c d e f g Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS (January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse. 39 (1): 32–41. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707.
  9. ^ a b c d e f g h i j Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA (October 2003). "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. doi:10.1124/jpet.103.053975. PMID 12954796.
  10. ^ 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 (2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology. 38 (4): 552–562. doi:10.1038/npp.2012.204. PMC 3572453. PMID 23072836.
  11. ^ Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV (April 2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology. 37 (5): 1192–203. doi:10.1038/npp.2011.304. PMC 3306880. PMID 22169943.
  12. ^ a b 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. Retrieved 2024-08-31.