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Details

Stereochemistry RACEMIC
Molecular Formula C11H17NO.ClH
Molecular Weight 215.72
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLEPHEDRINE HYDROCHLORIDE, (±)-

SMILES

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

InChI

InChIKey=NTCYWJCEOILKNG-ROLPUNSJSA-N
InChI=1S/C11H17NO.ClH/c1-9(12(2)3)11(13)10-7-5-4-6-8-10;/h4-9,11,13H,1-3H3;1H/t9-,11-;/m0./s1

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C11H17NO
Molecular Weight 179.2588
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

2013
589
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Methcathinone: a new postindustrial drug.
2005-10-04
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
Patents

Patents

20010010825
12
JP2010120932A
4
JPH09143074A
4
JPH1171281A
8

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:24:05 GMT 2025
Edited
by admin
on Mon Mar 31 18:24:05 GMT 2025
Record UNII
99214P83XM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYLEPHEDRINE HYDROCHLORIDE, (±)-
Common Name English
DL-METHYLEPHEDRINE HYDROCHLORIDE
JAN  
Preferred Name English
METHYLEPHEDRINE HYDROCHLORIDE [MART.]
Common Name English
2-DIMETHYLAMINO-1-PHENYLPROPANOL HYDROCHLORIDE
Systematic Name English
.ALPHA.-(1-(DIMETHYLAMINO)ETHYL)BENZENEMETHANOL HYDROCHLORIDE
Systematic Name English
METHYLEPHEDRINE HYDROCHLORIDE, DL-
Common Name English
Methylephedrine hydrochloride-dl [WHO-DD]
Common Name English
N,N-DIMETHYLNOREPHEDRINE HYDROCHLORIDE
Common Name English
N-METHYLEPHEDRINE DL-FORM HYDROCHLORIDE [MI]
Common Name English
METHYLEPHEDRINE HYDROCHLORIDE-DL
WHO-DD  
Common Name English
METHEPH
Brand Name English
BENZENEMETHANOL, .ALPHA.-(1-(DIMETHYLAMINO)ETHYL)-, HYDROCHLORIDE, (R*,S*)-(±)-
Common Name English
N-METHYLEPHEDRINE HYDROCHLORIDE, DL-
Common Name English
DL-METHYLEPHEDRINE HYDROCHLORIDE [JAN]
Common Name English
ERYTHRO-.ALPHA.-(1-(DIMETHYLAMINO)ETHYL)BENZYL ALCOHOL HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C87053
Created by admin on Mon Mar 31 18:24:05 GMT 2025 , Edited by admin on Mon Mar 31 18:24:05 GMT 2025
Code System Code Type Description
SMS_ID
100000085653
Created by admin on Mon Mar 31 18:24:05 GMT 2025 , Edited by admin on Mon Mar 31 18:24:05 GMT 2025
PRIMARY
CAS
18760-80-0
Created by admin on Mon Mar 31 18:24:05 GMT 2025 , Edited by admin on Mon Mar 31 18:24:05 GMT 2025
PRIMARY
FDA UNII
99214P83XM
Created by admin on Mon Mar 31 18:24:05 GMT 2025 , Edited by admin on Mon Mar 31 18:24:05 GMT 2025
PRIMARY
EVMPD
SUB14556MIG
Created by admin on Mon Mar 31 18:24:05 GMT 2025 , Edited by admin on Mon Mar 31 18:24:05 GMT 2025
PRIMARY
RXCUI
1311544
Created by admin on Mon Mar 31 18:24:05 GMT 2025 , Edited by admin on Mon Mar 31 18:24:05 GMT 2025
PRIMARY RxNorm
DRUG BANK
DBSALT001572
Created by admin on Mon Mar 31 18:24:05 GMT 2025 , Edited by admin on Mon Mar 31 18:24:05 GMT 2025
PRIMARY
ECHA (EC/EINECS)
242-557-4
Created by admin on Mon Mar 31 18:24:05 GMT 2025 , Edited by admin on Mon Mar 31 18:24:05 GMT 2025
PRIMARY
DAILYMED
99214P83XM
Created by admin on Mon Mar 31 18:24:05 GMT 2025 , Edited by admin on Mon Mar 31 18:24:05 GMT 2025
PRIMARY
MERCK INDEX
m7410
Created by admin on Mon Mar 31 18:24:05 GMT 2025 , Edited by admin on Mon Mar 31 18:24:05 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1589978
Created by admin on Mon Mar 31 18:24:05 GMT 2025 , Edited by admin on Mon Mar 31 18:24:05 GMT 2025
PRIMARY
NCI_THESAURUS
C77293
Created by admin on Mon Mar 31 18:24:05 GMT 2025 , Edited by admin on Mon Mar 31 18:24:05 GMT 2025
PRIMARY
Related Record Type Details
Structure of METHYLEPHEDRINE, (±)-
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of METHYLEPHEDRINE, (±)-
ACTIVE MOIETY
NIH
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