Etafedrine

Etafedrine
Systematic (IUPAC) name
(1R,2S)-N-ethyl-N-methyl-2-amino-1-phenylpropan-1-ol
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 7681-79-0
ATC code None
PubChem CID 10734
UNII 2Y6VQU63E8 YesY
Chemical data
Formula C12H19NO 
Mol. mass 193.285 g/mol
 YesY(what is this?)  (verify)

Etafedrine (INN) or ethylephedrine is a long-acting bronchodilator and has the brand name Nethaprin. It was previously commercially available as both the free base and as the hydrochloride salt from Sanofi-Aventis but is now no longer marketed.

Contents

Pharmacology

Unlike ephedrine and tyramine, etafedrine does not induce the release of epinephrine or norepinephrine and instead acts as a selective β-adrenergic receptor agonist, thereby mediating its bronchodilator effects.[1]

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:[2]

Etafedrine Synthesis (1R,2S).png

See also

References

  1. ^ Lindmar R, Löffelholz K, Stieh-Koch U (1985). "On the mechanism of bronchodilatation by etafedrine". Arzneimittel-Forschung 35 (3): 602–4. PMID 4039586. 
  2. ^ 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.