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Etafedrine: Wikis

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Etafedrine
Systematic (IUPAC) name
(1R,2S)- N-ethyl- N-methyl- 2-amino- 1-phenylpropan- 1-ol
Identifiers
CAS number 7681-79-0
ATC code none
PubChem 10734
Chemical data
Formula C 12H19NO 
Mol. mass 193.285 g·mol−1
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

Etafedrine (INN) or ethylephedrine is a long-acting bronchodilator and has the brand name Nethaprin. It is commercially available as both the free base, and as the hydrochloride salt.

It is no longer marketed by Sanofi-Aventis.

Synthesis

Although there are four possible stereoisomers of ethylephedrine, the pharmacological agent is the (1R, 2S) form. This isomer may be synthesized by alkylating naturally-occurring ephedrine with ethyl iodide. The hydrochloride may be prepared by passing hydrogen chloride through a solution of ethylephedrine in diethyl ether:[1]

Etafedrine Synthesis (1R,2S).png

References

  1. ^ Takeo Ueda,Shigeshi Toyoshima,Kiyoshi Takahashi and Masako Muraoka (1955). "Studies on Syntheses and Pharmacological Effects of N-Alkylephedrines and their Ammonium Salt Derivatives" (Free full text). Pharm. Bull. (Japan) 3 (6): 465–468. http://www.journalarchive.jst.go.jp/jnlpdf.php?cdjournal=cpb1953&cdvol=3&noissue=6&startpage=465&lang=en&from=jnltoc.  
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