Dioxifedrine - Misplaced Pages

Sympathomimetic that was never marketed

Not to be confused with Dioxethedrin. Pharmaceutical compound

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-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
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. It is described as a β-adrenergic receptor agonist and bronchodilator. 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). Analogues of dioxifedrine include dioxethedrin (α-methyl-N-ethylnorepinephrine), corbadrine (levonordefrin; α-methylnorepinephrine), and α-methyldopamine.

References

^ 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.
^ "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.

Adrenergic receptor modulators

α₁

Agonists

Antagonists

Abanoquil
Ajmalicine
Alfuzosin
Anisodamine
Anisodine
Atiprosin
Atypical antipsychotics (e.g., brexpiprazole, clozapine, olanzapine, quetiapine, risperidone)
Benoxathian
Beta blockers (e.g., adimolol, amosulalol, arotinolol, carvedilol, eugenodilol, labetalol)
Buflomedil
Bunazosin
Corynanthine
Dapiprazole
Domesticine
Doxazosin
Ergolines (e.g., acetergamine, ergotamine, dihydroergotamine, lisuride, nicergoline, terguride)
Etoperidone
Fenspiride
Hydroxyzine
Indoramin
Ketanserin
L-765,314
mCPP
Mepiprazole
Metazosin
Monatepil
Moxisylyte
Naftopidil
Nantenine
Neldazosin
Niaprazine
Niguldipine
Pardoprunox
Pelanserin
Perlapine
Phendioxan
Phenoxybenzamine
Phentolamine
Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione)
Piperoxan
Prazosin
Quinazosin
Quinidine
Silodosin
Spegatrine
Spiperone
Talipexole
Tamsulosin
Terazosin
Tiodazosin
Tolazoline
Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin)
Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine)
Trimazosin
Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine)
Urapidil
WB-4101
Zolertine

α₂

Agonists

Antagonists

1-PP
Adimolol
Amesergide
Aptazapine
Atipamezole
Atypical antipsychotics (e.g., asenapine, brexpiprazole, clozapine, lurasidone, olanzapine, paliperidone, quetiapine, risperidone, zotepine)
Azapirones (e.g., buspirone, gepirone, ipsapirone, tandospirone)
BRL-44408
Buflomedil
Cirazoline
Efaroxan
Esmirtazapine
Fenmetozole
Fluparoxan
Idazoxan
Ketanserin
Lisuride
mCPP
Mianserin
Mirtazapine
NAN-190
Pardoprunox
Phentolamine
Phenoxybenzamine
Piperoxan
Piribedil
Rauwolscine
Rotigotine
Setiptiline
Spegatrine
Spiroxatrine
Sunepitron
Terguride
Tolazoline
Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine)
Yohimbine

Agonists

Abediterol
Alifedrine
Amibegron
Arbutamine
Arformoterol
Arotinolol
BAAM
Bambuterol
Befunolol
Bitolterol
Broxaterol
Buphenine
Carbuterol
Carmoterol
Cimaterol
Clenbuterol
Colterol
Corbadrine
Denopamine
Deoxyepinephrine (epinine, N-methyldopamine)
Dipivefrine
Dobutamine
Dopamine
Dopexamine
Droxidopa (L-DOPS)
Epinephrine
Etafedrine
Etilefrine
Etilevodopa
Ethylnorepinephrine
Eugenodilol
Fenoterol
Formoterol
Hexoprenaline
Higenamine
Ibopamine
Indacaterol
Isoetarine
Isoprenaline
Isoxsuprine
L-DOPA (levodopa)
L-Phenylalanine
L-Tyrosine
Levosalbutamol
Lubabegron
Mabuterol
Melevodopa
Methoxyphenamine
Methyldopa
Mirabegron
Norepinephrine
Orciprenaline
Oxyfedrine
PF-610355
Phenylpropanolamine
Pirbuterol
Prenalterol
Ractopamine
Procaterol
Reproterol
Rimiterol
Ritodrine
Salbutamol
Salmeterol
Solabegron
Terbutaline
Tretoquinol
Tulobuterol
Vibegron
Vilanterol
Xamoterol
XP21279
Zilpaterol
Zinterol

Antagonists

See also: Receptor/signaling modulators
Dopaminergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

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

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