2-Ethylmethylamino-1-phenylpropan-1-ol
PubChem CID
10734
Structure
Molecular Formula
Synonyms
- ETAFEDRINE
- Ethylephedrine
- Menetryl
- 7681-79-0
- Etafedrine hydrochloride
Molecular Weight
193.28 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-03-27
- Modify:2025-02-01
Description
Etafedrine is an alkylbenzene.
Etafedrine (INN) or ethylephedrine is a long-acting bronchodilator and has been an ingredient combined with other drugs in the brand names Nethaprin and Dalmacol. It was previously available as both the free base and as the hydrochloride salt manufactured by Sanofi-Aventis (now Sanofi) has been discontinued. Ethylephedrine is be formed by alkylating ephedrine with ethyl iodide. The hydrochloride is be prepared by passing hydrogen chloride through a solution of ethylephedrine in diethyl ether. This belongs to the family of medications called decongestants. It acts by narrowing blood vessels in the nasal passages, helping to relieve nasal congestion.
See also: Etafedrine (annotation moved to).
Chemical Structure Depiction
2-[ethyl(methyl)amino]-1-phenylpropan-1-ol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
IRVLBORJKFZWMI-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CCN(C)C(C)C(C1=CC=CC=C1)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C12H19NO
Computed by PubChem 2.2 (PubChem release 2021.10.14)
5591-29-7 (hydrochloride)
- etafedrine
- etafedrine hydrochloride
- etafedrine hydrochloride, (R-(R*,S*))-isomer
- etafedrine, (R*,S*)-isomer
- etafedrine, R-(R*,S*)
- etaphedrine
- L-N-ethylephedrine
- ETAFEDRINE
- Ethylephedrine
- Menetryl
- 7681-79-0
- Etafedrine hydrochloride
- 2-[ethyl(methyl)amino]-1-phenylpropan-1-ol
- 2-Ethylmethylamino-1-phenylpropan-1-ol
- Etafedrinum
- Novedrine
- Etafedrine, (-)-
- Etafedrine [INN:BAN]
- Etafedrinum [INN-Latin]
- Benzenemethanol, .alpha.-[1-(ethylmethylamino)ethyl]-
- Etafedrina
- EINECS 231-677-2
- 2-Methylethylamino-1-phenyl-1-propanol
- alpha-(1-(Ethylmethylamino)ethyl)benzyl alcohol
- SCHEMBL249050
- Benzenemethanol, alpha-(1-(ethylmethylamino)ethyl)-
- Benzenemethanol, .alpha.-[1-(ethylmethylamino)ethyl]-, [R-(R*,S*)]-
- CHEMBL2110926
- DTXSID20864101
- CHEBI:134847
- IRVLBORJKFZWMI-UHFFFAOYSA-N
- AKOS005361212
- NCGC00510907-01
- NS00003054
- 2-[Ethyl(methyl)amino]-1-phenyl-1-propanol #
- EN300-1608668
- .alpha.-[1-(Ethylmethylamino)ethyl]benzenemethanol
- Benzyl alcohol, alpha-(1-(ethylmethylamino)ethyl)-
- Z854201840
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
193.28 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
2.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
193.146664230 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
193.146664230 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
23.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
14
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
154
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
108-110
MSDS
Standard non-polar
1465 , 1500
NIST Number
246127
Library
Main library
Total Peaks
23
m/z Top Peak
86
m/z 2nd Highest
58
m/z 3rd Highest
77
Thumbnail
NIST Number
120684
Library
Main library
Total Peaks
13
m/z Top Peak
86
m/z 2nd Highest
58
m/z 3rd Highest
87
Thumbnail
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Etafedrine (annotation moved to)
Conditions characterized by bronchial congestion and bronchospasm when an expectorant or bronchodilator action is required, such as acute bronchitis, acute episodes of chronic bronchitis and bronchial asthma,.
Etafedrine helps to control the cough which is associated with irritation of the mouth and throat that is not alleviated by cough medications that are less strong. The results of one study in 48 individuals showed that lung FEV1 (forced expiratory volume) and lung VC (vital capacity) were significantly improved with etafedrine, sleep improved, and patients showed improved appetite in addition to the suppression of cough.
Absorption
Similar to its parent drug, ephedrine, it is readily and completely absorbed from the gastrointestinal tract; plasma peak concentrations are reached an hour after ingestion. A single oral dose of 24 mg produced an average peak plasma concentration of 0.10 mg/L.
Route of Elimination
Excreted mainly in the urine.
Volume of Distribution
Similar to ephedrine, at about 3L/kg.
It has a plasma half-life ranging from 3 to 6 hours depending on urinary pH.
A sympathomimetic agent, etafedrine acts on the sympathetic receptors of the bronchial tree, relieving spasm in a manner similar to that of ephedrine. Etafedrine acts as a selective β adrenoreceptor agonist, thereby mediating its bronchodilator effects without increasing norepinephrine release. This is distinctly different from ephedrine and tyramine which trigger the release of epinephrine or norepinephrine. N-ethylation of ephedrine suppresses the indirect sympathomimetic activity and markedly enhances the efficacy on beta 2- adrenoceptors.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=IRVLBORJKFZWMI-UHFFFAOYSA-N
- Take with a full glass of water.
- Take with or without food.
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/
- ChemIDplusEtafedrine [INN:BAN]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0007681790ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useEtafedrinehttps://www.drugbank.ca/drugs/DB11587
- EPA DSSTox2-Ethylmethylamino-1-phenylpropan-1-olhttps://comptox.epa.gov/dashboard/DTXSID20864101CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- European Chemicals Agency (ECHA)LICENSEUse of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.https://echa.europa.eu/web/guest/legal-noticeEtafedrine hydrochloridehttps://echa.europa.eu/substance-information/-/substanceinfo/100.024.546
- ChEBI
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.html
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.html
- Metabolomics Workbench
- NCI Thesaurus (NCIt)LICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuse
- NIST Mass Spectrometry Data CenterLICENSEData covered by the Standard Reference Data Act of 1968 as amended.https://www.nist.gov/srd/public-lawBenzenemethanol, .alpha.-[1-(ethylmethylamino)ethyl]-http://www.nist.gov/srd/nist1a.cfm
- SpectraBase
- Springer Nature
- WikipediaEtafedrinehttps://en.wikipedia.org/wiki/Etafedrine
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.html
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/NORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 388647205https://pubchem.ncbi.nlm.nih.gov/substance/388647205
- NCBI
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