Etafedrine
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| 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 |
| ChemSpider | 85308 |
| UNII | 2Y6VQU63E8  |
| Chemical data | |
| Formula | C12H19NO |
| Mol. mass | 193.285 g/mol |
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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.
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[edit] 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]
[edit] 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]
[edit] See also
[edit] References
- ^ Lindmar R, Löffelholz K, Stieh-Koch U (1985). "On the mechanism of bronchodilatation by etafedrine". Arzneimittel-Forschung 35 (3): 602–4. PMID 4039586.
- ^ 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.
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