Racephedrine

Overview

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.[1–9] WP⚠ A table follows this text in the source and is not copied here. Open the source to see it.

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.[10] WP

Drug class

Norepinephrine releasing agent Sympathomimetic Bronchodilator Psychostimulant WP

From the Wikipedia article's infobox.

Chemistry

Formula

C10H15NO PC

CAS number

53214-57-6 PC

Molar mass (g/mol)

165.23 PC

IUPAC name (computed by PubChem)

2-(methylamino)-1-phenylpropan-1-ol PC

SMILES

CC(C(C1=CC=CC=C1)O)NC PC

InChIKey

KWGRBVOPPLSCSI-UHFFFAOYSA-N PC

PubChem CID

5032

IUPAC name

2-(methylamino)-1-phenylpropan-1-ol WP

Mixing

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Schweizerischer Apotheker-Verein. Index Nominum 2000: International Drug Directory. 2000
2. Harm reduction site Racephedrine: Uses, Interactions, Mechanism of Action. 31 December 1995
3. Journal / agency Racephedrine
4. Journal / agency Tapay NJ. A racephedrine-phenyltoloxamine-containing compound (Ephoxamine) in the treatment of bronchial asthma. Curr Ther Res Clin Exp. July 1961. PMID 13775237
5. Journal / agency 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. Therapie. 1968. PMID 5744603
6. Journal / agency Rothman RB, Baumann MH. Monoamine transporters and psychostimulant drugs. Eur. J. Pharmacol. 2003. doi:10.1016/j.ejphar.2003.08.054 · PMID 14612135
7. Journal / agency Rothman RB, Baumann MH. Therapeutic potential of monoamine transporter substrates. Curr Top Med Chem. 2006. doi:10.2174/156802606778249766 · PMID 17017961
8. Journal / agency 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. January 2001. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3 · PMID 11071707
9. Journal / agency 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. October 2003. doi:10.1124/jpet.103.053975 · PMID 12954796
10. Other Project Label: Alphabetical Listing by Drug Product. 1979

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