Etafedrine

Etafedrine
Clinical data
Trade names	Menetyl; Nethaprin; Novedrin
Other names	Ethylephedrine; N-Ethylephedrine
ATC code	None;
Legal status
Legal status	AU: S2 (Pharmacy medicine); BR: Class D1 (Drug precursors); Withdrawn from market;
Identifiers
	IUPAC name (1R,2S)-2-[Ethyl(methyl)amino]-1-phenyl-1-propanol;
CAS Number	48141-64-6 ;
PubChem CID	10734;
DrugBank	DB11587;
ChemSpider	85308 ;
UNII	2Y6VQU63E8;
ChEBI	CHEBI:134847;
ChEMBL	ChEMBL2110926;
CompTox Dashboard (EPA)	DTXSID201016521 ;
ECHA InfoCard	100.051.218
Chemical and physical data
Formula	C12H19NO
Molar mass	193.290 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O[C@H](c1ccccc1)[C@@H](N(CC)C)C;
	InChI InChI=1S/C12H19NO/c1-4-13(3)10(2)12(14)11-8-6-5-7-9-11/h5-10,12,14H,4H2,1-3H3/t10-,12-/m0/s1 ; Key:IRVLBORJKFZWMI-JQWIXIFHSA-N ;
	(verify)

Etafedrine (INNTooltip International Nonproprietary Name, BANTooltip British Approved Name), sold under the brand name Nethaprin among others and also known as N-ethylephedrine, is a sympathomimetic agent used as a bronchodilator to treat asthma.^[2]^[3]^[4] It was previously commercially available as both the free base and as the hydrochloride salt from Sanofi-Aventis (now Sanofi) but is now no longer marketed.

Pharmacology

Unlike ephedrine and tyramine, etafedrine does not induce the release of epinephrine or norepinephrine and instead acts as a selective β₂-adrenergic receptor agonist, thereby mediating its bronchodilator effects.^[4]^[5]

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
^ Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 503. ISBN 978-1-4757-2085-3. Retrieved 30 August 2024.
^ Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 114. ISBN 978-94-011-4439-1. Retrieved 30 August 2024.
^ ^a ^b "Etafedrine: Uses, Interactions, Mechanism of Action". DrugBank Online. 31 December 1983. Retrieved 30 August 2024.
^ Lindmar R, Löffelholz K, Stieh-Koch U (1985). "On the mechanism of bronchodilatation by etafedrine". Arzneimittel-Forschung. 35 (3): 602–604. PMID 4039586.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.

[Elks2014-2] Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 503. ISBN 978-1-4757-2085-3. Retrieved 30 August 2024.

[MortonHall2012-3] Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 114. ISBN 978-94-011-4439-1. Retrieved 30 August 2024.

[DrugBank-4] "Etafedrine: Uses, Interactions, Mechanism of Action". DrugBank Online. 31 December 1983. Retrieved 30 August 2024.

[LindmarLöffelholzStieh=Koch1985-5] Lindmar R, Löffelholz K, Stieh-Koch U (1985). "On the mechanism of bronchodilatation by etafedrine". Arzneimittel-Forschung. 35 (3): 602–604. PMID 4039586.

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[2]

[3]

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[5]

Pharmacology

See also

References