Dioxifedrine

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;

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]

References

^ ^a ^b ^c ^d 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.
^ ^a ^b "Dioxifedrine". PubChem. U.S. National Library of Medicine. Retrieved 2 September 2024.
^ "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.
^ "Dioxifedrine". CAS Common Chemistry. American Chemical Society. 2 September 2024. CAS Registration Number 10329-60-9. Retrieved 2 September 2024.
^ "DIOXIFEDRINE". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS). Retrieved 2 September 2024.
^ "Dioxifedrine". NCI Thesaurus. U.S. National Cancer Institute. Code C65417.

This drug article relating to the cardiovascular system is a stub. You can help Wikipedia by expanding it.

[Elks2014-1] 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.

[PubChem-2] "Dioxifedrine". PubChem. U.S. National Library of Medicine. Retrieved 2 September 2024.

[WHO-INN-2003-3] "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.

[CASCommonChem-4] "Dioxifedrine". CAS Common Chemistry. American Chemical Society. 2 September 2024. CAS Registration Number 10329-60-9. Retrieved 2 September 2024.

[InxightDrugs-5] "DIOXIFEDRINE". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS). Retrieved 2 September 2024.

[NCIThesaurus-6] "Dioxifedrine". NCI Thesaurus. U.S. National Cancer Institute. Code C65417.

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v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine