METHYLEPHEDRINE, (+)-

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 Search

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

Molecular Formula	C11H17NO
Molecular Weight	179.2588
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2327112
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine receptors 2 Target ID: Histamine receptors Sources: https://www.ncbi.nlm.nih.gov/pubmed/8990487	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: http://www.rad-ar.or.jp/siori/english/kekka_plain.cgi?n=1463	Palliative		Approved 8583	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

Title	Date	PubMed
Methylephedrine concentrations in blood and urine specimens.	1998-07-29	9681334
[Caffeine-11C, ephedrine-11C and methylephedrine-11C: Synthesis and distribution in mice (author's transl)].	1978-08	734163
[Broncholytic effect of methylephedrine in acute study].	1974-09	4479800
[Comparative studies on a broncholytic and circulatory effect of methylephedrine and ephedrine].	1970-02-15	5522079

Patents

Sample Use Guides

In Vivo Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:29:24 GMT 2025` Edited by `admin` on `Mon Mar 31 21:29:24 GMT 2025`
Record UNII	VP306Z33KI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(+)-METHYLEPHEDRINE

Preferred Name

English

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

(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