Basic information
- CAS
1201-56-5- Standard SMILES
C[C@@H]([C@H](O)c1ccccc1)N(C)C- InChIKey
FMCGSUUBYTWNDP-ONGXEEELSA-N- Molecular formula
- C11H17NO
- Average molar mass
- 179.26 g/mol
- Monoisotopic mass
- 179.13101416
Overview
(1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol is an alkylbenzene.
Names & identifiers
- Preferred name
- Methylephedrine
- IUPAC
- (1R,2S)-2-(dimethylamino)-1-phenylpropan-1-ol
Names & synonyms
Methylephedrine552-79-4(1R,2S)-2-Dimethylamino-1-phenyl-1-propanol60VH42A1KJNSC-760389Benzenemethanol, alpha-((1S)-1-(dimethylamino)ethyl)-, (alphaR)-(1R)-2-(dimethylamino)-1-phenylpropan-1-olRefChem:1089689209-022-72-(dimethylamino)-1-phenylpropan-1-ol(1R,2S)-2-(dimethylamino)-1-phenylpropan-1-ol(-)-N-Methylephedrine
Show more names
(-)-methylephedrinedl-methylephedrineMethylephedrine, (+/-)-DTXSID7045992Methylephedrine, DL-SHS9PGQ2LS(+/-)-Methylephedrine(+/-)-n-methylephedrine
Database identifiers
- CAS
1201-56-5、552-79-4- PubChem CID
- 64782
- DTXSID
DTXSID7045992- ChEMBL
CHEMBL1589978、CHEMBL445001- ChEBI
CHEBI:113556- UNII
- 60VH42A1KJ、SHS9PGQ2LS
- EC Number
- 209-022-7、214-859-6
- Nikkaji
- J21.604F
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 23.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 141
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP1.7
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Chemistry & industry
Pharmacology
Pharmacodynamics
This drugs acts as an antitussive, bronchodilator, and adrenergic receptor agonist. It stimulates the alpha and beta adrenergic receptors, relieving cough and congestion. As with other adrenomimetic amines, the drugs in this class are much less potent than norepinephrine itself. Members of this class of drugs increase both systolic and diastolic blood pressure, cardiac contractility, and cardiac output; in general, however, they do not increase heart rate. Bronchial smooth muscle relaxation of prolonged duration occurs, and pupils dilate.
Mechanism of Action
The pharmacology of methylephedrine is similar to that of other members of the ephedra alkaloid class of drugs. These compounds are sympathomimetic amines because they mimic the effects of the catecholamines on the sympathetic nervous system. These alkaloids permeate the blood-brain barrier and have a direct central nervous system stimulant effect with peripheral effects; the peripheral effects are indirect and primarily mediated by norepinephrine release. Methylephedrine expands the bronchia by relaxing the bronchial muscles. The decrease in urination with sympathomimetic use is increased through activation of the alpha-adrenoceptors of the smooth muscles of the bladder.
Biological Half-Life3-6 hours (Ephedrine).
Metabolism/MetabolitesMethylephedrine is metabolized to give ephedrine and norephedrine.
Absorption, Distribution and Excretion
Methylephedrine is rapidly absorbed following oral administration. Peak plasma concentrations of ephedrine (from which methylephedrine is derived) occur 2-3h after administration. Due to the fact that methylephedrine is a derivative of ephedrine, peak plasma concentrations are likely similar.
The primary compound excreted in urine is unchanged methylephedrine (33-40% of dose), followed by the metabolite _methylephedrine-N-oxide_ (15% of dose), and approximately 8% of the dose excreted as ephedrine after 24 hours. About 70% of the dose is excreted in the urine as metabolites over 72 hours. Alkaline urine reduces elimination to 20-35% of the dose.
Ephedrine: 2.5-3.0 L/kg. Methylephedrine is a derivative of ephedrine and quickly distributed throughout the body.
Uses & manufacturing
Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Related reactions
6 records
Compound notes
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