METHYLEPHEDRINE, (±)-

Details

Stereochemistry	RACEMIC
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-ONGXEEELSA-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-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8951157

L-methylephedrine is an isomer of DL form, which possesses beta 1-adrenoceptor agonist activity, while d-isomer is suggested to have only low or no affinity for beta 1-adrenoceptors.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-1 adrenergic receptor 163 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8951157	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Methcathinone: a new postindustrial drug.	2005-10-04	15919169
Chronotropic effects of optical isomers of ephedrine and methylephedrine in the isolated rat right atria and in vitro assessment of direct and indirect actions on beta 1-adrenoceptors.	1996-11	8951157

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Effects of optical isomers of methylephedrine (MEP) on the spontaneous beating rate of isolated right atrium of normal and reserpinized rat were investigated to assess direct and indirect actions on beta 1-adrenoceptors. l-MEP (10(-5) - 3 x 10(-4) M) showed slight increase in heart rate. In addition, d-MEP (3 x 10(-5) - 3 x 10(-4) M) caused a decrease in heart rate. Positive chronotropic effects of l-MEP was attenuated by pretreatment with atenolol ( a selective beta 1-adrenoceptor antagonist) or reserpine treatment (8 mg/kg, s.c.). l-MEP has beta 1-adrenoceptor agonist activity, while d-MEP is suggested to have only low or no affinity for beta 1-adrenoceptors. The relatively weak activity of l-MEP is believed to be mainly mediated by released noradrenaline.

Name

Type

Language

METHYLEPHEDRINE, (±)-

Common Name

English

(±)-METHYLEPHEDRINE

Preferred Name

English

(±)-N-METHYLEPHEDRINE

Common Name

English

N-METHYLEPHEDRINE DL-FORM [MI]

Common Name

English

METHYLEPHEDRINE, DL-

Common Name

English

BENZENEMETHANOL, .ALPHA.-((1R)-1-(DIMETHYLAMINO)ETHYL)-, (.ALPHA.S)-REL-

Common Name

English

DL-METHYLEPHEDRINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C87053