Dioxifedrine

Not to be confused with Dioxethedrin.

Dioxifedrine (INNTooltip International Nonproprietary Name), or dioxifedrin, also known as α-methylepinephrine or as 3,4-dihydroxyephedrine, is a sympathomimetic medication that was never marketed.^[1][2][3][4] It is described as a β-adrenergic receptor agonist and bronchodilator.^[1][5][6] The drug is a substituted phenethylamine and amphetamine and is the catecholamine (3,4-dihydroxylated) derivative of ephedrine and the amphetamine (α-methylated) analogue of epinephrine (adrenaline).^[1][2] Analogues of dioxifedrine include dioxethedrin (α-methyl-N-ethylnorepinephrine), corbadrine (levonordefrin; α-methylnorepinephrine), and α-methyldopamine.^[1]

Dioxifedrine

Clinical data
Other names	Dioxifedrin; α-Methylepinephrine; α-Methyladrenaline; 3,4-Dihydroxyephedrine; Dioxyephedrine; Sor-N 49; Diphedran; LD-1205; 3,4,β-Trihydroxy-α,N-dimethylphenethylamine; 3,4,β-Trihydroxy-N-methylamphetamine
Identifiers
IUPAC name 4-[1-hydroxy-2-(methylamino)propyl]benzene-1,2-diol
CAS Number	10329-60-9
PubChem CID	13683
ChemSpider	13093
UNII	CF48QOH154
ChEMBL	ChEMBL416557
CompTox Dashboard (EPA)	DTXSID40864249
ECHA InfoCard	100.030.639
Chemical and physical data
Formula	C10H15NO3
Molar mass	197.234 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C(C1=CC(=C(C=C1)O)O)O)NC
InChI InChI=1S/C10H15NO3/c1-6(11-2)10(14)7-3-4-8(12)9(13)5-7/h3-6,10-14H,1-2H3 Key:DDBFLXGTCAVAFD-UHFFFAOYSA-N

References

1. Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 447. ISBN 978-1-4757-2085-3. Retrieved 2 September 2024.
2. "Dioxifedrine". PubChem. U.S. National Library of Medicine. Retrieved 2 September 2024.
3. "The use of common stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances" (PDF). Programme on International Nonproprietary Names (INN). World Health Organization (WHO). 2002.
4. "Dioxifedrine". CAS Common Chemistry. American Chemical Society. 2 September 2024. CAS Registration Number 10329-60-9. Retrieved 2 September 2024.
5. "DIOXIFEDRINE". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS). Retrieved 2 September 2024.
6. "Dioxifedrine". NCI Thesaurus. U.S. National Cancer Institute. Code C65417.