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Details

Stereochemistry RACEMIC
Molecular Formula C11H15NO
Molecular Weight 177.2429
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METAMFEPRAMONE

SMILES

CC(N(C)C)C(=O)C1=CC=CC=C1

InChI

InChIKey=KBHMHROOFHVLBA-UHFFFAOYSA-N
InChI=1S/C11H15NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9H,1-3H3

HIDE SMILES / InChI

Molecular Formula C11H15NO
Molecular Weight 177.2429
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Metamfepramone (dimethylcathinone, dimethylpropion, and dimepropion) was synthesized by various routes in the 1930s and 1940s and clinically evaluated as anorectic as well as a treatment of hypotension and symptoms of the common cold. It was widely used for the treatment of the common cold or hypotonic conditions. Due to its stimulating properties and its rapid metabolism resulting in major degradation products such as methylpseudoephedrine and methcathinone, it has been considered relevant for doping controls by the World Anti-Doping Agency (WADA). Metamfepramone was marketed as an appetite suppressant, but was made illegal in 2006.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Choline pivaloyl esters improve in rats cognitive and memory performances impaired by scopolamine treatment or lesions of the nucleus basalis of Meynert.
2004 Feb 19
Doping control analysis of metamfepramone and two major metabolites using liquid chromatography-tandem mass spectrometry.
2009
Patents

Patents

Sample Use Guides

One capsule (accounting for a total of 10mg of metamfepramone-HCl), was orally ingested
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:54:16 GMT 2023
Edited
by admin
on Fri Dec 15 15:54:16 GMT 2023
Record UNII
04A0P12FH2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METAMFEPRAMONE
INN   MI   WHO-DD  
INN  
Official Name English
METAMFEPRAMONE [MI]
Common Name English
DIMEPROPION
Common Name English
DIMETHYLCATHINONE
Common Name English
MG-559
Code English
N-METHYLEPHEDRONE
Common Name English
MG 559
Code English
J8.560J
Code English
METAMFEPYRAMONE
Common Name English
.ALPHA.-(DIMETHYLAMINO)PROPIOPHENONE
Systematic Name English
BENZOYL-.ALPHA.-(DIMETHYLAMINO)ETHANE
Systematic Name English
2-(DIMETHYLAMINO)-1-PHENYLPROPANONE
Common Name English
Metamfepramone [WHO-DD]
Common Name English
2-(DIMETHYLAMINO)PROPIOPHENONE
Systematic Name English
metamfepramone [INN]
Common Name English
NSC-234706
Code English
DIMETHYLPROPION
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
Code System Code Type Description
NSC
234706
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
MESH
C034349
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
INN
1587
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
NCI_THESAURUS
C83947
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
EVMPD
SUB08808MIG
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105245
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
CAS
15351-09-4
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
WIKIPEDIA
METAMFEPRAMONE
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
ECHA (EC/EINECS)
239-384-1
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID7057650
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
PUBCHEM
71872
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
SMS_ID
100000081215
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
FDA UNII
04A0P12FH2
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
DRUG CENTRAL
3772
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY
MERCK INDEX
m321
Created by admin on Fri Dec 15 15:54:16 GMT 2023 , Edited by admin on Fri Dec 15 15:54:16 GMT 2023
PRIMARY Merck Index
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY