Dioxethedrin

Dioxethedrin
Clinical data
Other names	Dioxethedrine; 3,4-Dihydroxy-N-ethylnorephedrine; 3,4,β-Trihydroxy-N-ethyl-α-methyl-β-phenethylamine; 3,4,β-Trihydroxy-N-ethylamphetamine; α-Methyl-N-ethylnorepinephrine
Identifiers
	IUPAC name 4-[2-(ethylamino)-1-hydroxypropyl]benzene-1,2-diol;
CAS Number	497-75-6;
PubChem CID	71632;
ChemSpider	64697;
UNII	82J92E653W;
ChEBI	CHEBI:134881;
ChEMBL	ChEMBL2110629;
CompTox Dashboard (EPA)	DTXSID00862044 ;
ECHA InfoCard	100.007.137
Chemical and physical data
Formula	C11H17NO3
Molar mass	211.261 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCNC(C)C(C1=CC(=C(C=C1)O)O)O;
	InChI InChI=1S/C11H17NO3/c1-3-12-7(2)11(15)8-4-5-9(13)10(14)6-8/h4-7,11-15H,3H2,1-2H3; Key:OHDICGSRVLBVLC-UHFFFAOYSA-N;

Dioxethedrin (INNTooltip International Nonproprietary Name), or dioxethedrine, also known as 3,4-dihydroxy-N-ethylnorephedrine, is a sympathomimetic medication.^[1]^[2]^[3] It was a component of the antitussive syrup Bexol (a combination of dioxethedrin, codeine, and promethazine).^[4]^[5] It is an ephedrine derivative (and hence is a phenethylamine and amphetamine) and is described as a bronchodilator and β-adrenergic receptor agonist.^[2]^[4] Analogues of dioxethedrin include dioxifedrine (α-methylepinephrine; 3,4-dihydroxyephedrine), corbadrine (levonordefrin; α-methylnorepinephrine), and α-methyldopamine.^[1]

References

^ ^a ^b Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 444. ISBN 978-1-4757-2085-3. Retrieved 1 September 2024.
^ ^a ^b Milne GW (2018). Drugs: Synonyms and Properties. Routledge Revivals. Taylor & Francis. p. 494. ISBN 978-1-351-78990-5. Retrieved 1 September 2024.
^ Pschyrembel W, Dornblüth O, Zink C (2012). "Dioxethedrin". Pschyrembel klinisches Wörterbuch: Mit klinischen Syndromen und Nomina Anatomica (in German). De Gruyter. p. 358. ISBN 978-3-11-150689-0. Retrieved 1 September 2024.
^ ^a ^b "Dioxethedrin Hydrochloride". Inxight Drugs. Retrieved 1 September 2024.
^ Portmann M, Delage R (1964). "[The Antitussive Combination Dioxethedrine-Codeine-Promethazine]". Revue de Laryngologie - Otologie - Rhinologie (in French). 85: 1073–1081. PMID 14266725.

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[Elks2014-1] Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 444. ISBN 978-1-4757-2085-3. Retrieved 1 September 2024.

[Milne2018-2] Milne GW (2018). Drugs: Synonyms and Properties. Routledge Revivals. Taylor & Francis. p. 494. ISBN 978-1-351-78990-5. Retrieved 1 September 2024.

[PschyrembelDornblüthZink2012-3] Pschyrembel W, Dornblüth O, Zink C (2012). "Dioxethedrin". Pschyrembel klinisches Wörterbuch: Mit klinischen Syndromen und Nomina Anatomica (in German). De Gruyter. p. 358. ISBN 978-3-11-150689-0. Retrieved 1 September 2024.

[InxightDrugs-4] "Dioxethedrin Hydrochloride". Inxight Drugs. Retrieved 1 September 2024.

[PortmannDelage1964-5] Portmann M, Delage R (1964). "[The Antitussive Combination Dioxethedrine-Codeine-Promethazine]". Revue de Laryngologie - Otologie - Rhinologie (in French). 85: 1073–1081. PMID 14266725.

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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