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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H17NO
Molecular Weight 179.2588
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLEPHEDRINE, (+)-

SMILES

C[C@H]([C@@H](O)C1=CC=CC=C1)N(C)C

InChI

InChIKey=FMCGSUUBYTWNDP-MWLCHTKSSA-N
InChI=1S/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/t9-,11-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9681334 http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=1310.12

Methylephedrine is one of the ephedra alkaloids that is found in varying amounts in different species of the plant genus Ephedra. Methylephedrine is a popular antitussive, bronchodilator, analgesic, antipyretic, and widely used mixed with other drugs in preparations for treatment of the common cold. N-Methylephedrine, its salts, optical isomers, and salts of optical isomers are in FDA list of Exempt chemical mixtures.

Originator

Sources: DOI: 10.1002/jlac.19294700110
Curator's Comment: L-form: Smith S. DOI: 10.1039/JR9270002056

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Sanwa

Approved Use

It is usually used in the treatment of cough associated with diseases such as bronchial asthma, cold, acute or chronic bronchitis, pulmonary tuberculosis, and upper airway inflammation.
PubMed

PubMed

TitleDatePubMed
[Comparative studies on a broncholytic and circulatory effect of methylephedrine and ephedrine].
1970 Feb 15
[Broncholytic effect of methylephedrine in acute study].
1974 Sep
[Caffeine-11C, ephedrine-11C and methylephedrine-11C: Synthesis and distribution in mice (author's transl)].
1978 Aug
Methylephedrine concentrations in blood and urine specimens.
1998 Jul-Aug
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: dl-methylephedrine hydrochloride
Take 0.25-0.5 g (25-50 mg of the active ingredient) at a time, 3 times daily
Route of Administration: Oral
In Vitro Use Guide
l-MEP inhibited the twitch response at high concentrations (3 x 10(-5)-10(-3) M). On the other hand, d-MEP showed the potentiation of twitch response, and competitively antagonized the twitch-inhibitory effect of clonidine (10(-9)-10(-6) M) with the pA2 value of 4.3 in the presence of prazosin.
Name Type Language
METHYLEPHEDRINE, (+)-
Common Name English
BENZENEMETHANOL, .ALPHA.-((1R)-1-(DIMETHYLAMINO)ETHYL)-, (.ALPHA.S)-
Systematic Name English
D-N-METHYLEPHEDRINE
Common Name English
(1S,2R)-N-METHYLEPHEDRINE
Common Name English
N-METHYLEPHEDRINE, D-
Common Name English
(+)-N-METHYLEPHEDRINE
Common Name English
METHYLEPHEDRINE, D-
Common Name English
(+)-METHYLEPHEDRINE
Common Name English
(1S,2R)-(+)-N-METHYLEPHEDRINE
Common Name English
(1S,2R)-2-DIMETHYLAMINO-1-PHENYLPROPANOL
Systematic Name English
N-METHYLEPHEDRINE D-FORM [MI]
Common Name English
L-(+)-ERYTHRO-N-METHYLEPHEDRINE
Common Name English
Code System Code Type Description
PUBCHEM
102023
Created by admin on Sat Dec 16 05:25:20 GMT 2023 , Edited by admin on Sat Dec 16 05:25:20 GMT 2023
PRIMARY
CAS
42151-56-4
Created by admin on Sat Dec 16 05:25:20 GMT 2023 , Edited by admin on Sat Dec 16 05:25:20 GMT 2023
PRIMARY
FDA UNII
VP306Z33KI
Created by admin on Sat Dec 16 05:25:20 GMT 2023 , Edited by admin on Sat Dec 16 05:25:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID20962313
Created by admin on Sat Dec 16 05:25:20 GMT 2023 , Edited by admin on Sat Dec 16 05:25:20 GMT 2023
PRIMARY
MERCK INDEX
m7410
Created by admin on Sat Dec 16 05:25:20 GMT 2023 , Edited by admin on Sat Dec 16 05:25:20 GMT 2023
PRIMARY Merck Index