U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C9H10N2O.C4H4O4
Molecular Weight 278.2607
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AMINOREX FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.NC1=NCC(O1)C2=CC=CC=C2

InChI

InChIKey=ZVAWZQUDKKABKR-WLHGVMLRSA-N
InChI=1S/C9H10N2O.C4H4O4/c10-9-11-6-8(12-9)7-4-2-1-3-5-7;5-3(6)1-2-4(7)8/h1-5,8H,6H2,(H2,10,11);1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Molecular Formula C9H10N2O
Molecular Weight 162.1885
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Aminorex is an anorectic stimulant drug. Aminorex inhibits norepinephrine and dopamine transporters with IC50 of 0.33 and 0.85 uM. It was briefly available as an appetite suppressant in the 1960s in Switzerland, Germany, and Austria, but was found to cause pronounced vasoconstriction in the pulmonary vasculature, and was withdrawn from the market in 1972 due to several cases of fatal and life-threatening pulmonary hypertension. In the USA aminorex is an illegal schedule I drug.

Approval Year

PubMed

PubMed

TitleDatePubMed
[A case of chronic pulmonary hypertension after fenfluramine intake].
1982 Nov 26
Pulmonary hypertension and dexfenfluramine.
1995
Aminorex, dexfenfluramine, and primary pulmonary hypertension.
1998 Apr
Monoclonal endothelial cells in appetite suppressant-associated pulmonary hypertension.
1998 Dec
[Development of pulmonary hypertension and multi-valvular damage caused by appetite depressants].
1998 Dec 1
Two different drug-induced pulmonary complications in a patient suffering from rheumatoid arthritis.
1998 May
[Obesity: principles of drug therapy].
2000 Aug
[Anorectics and pulmonary hypertension].
2000 Feb 16
Anorectic drugs and pulmonary hypertension from the bedside to the bench.
2001 Apr
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.
2001 Jan
[Drug induced pulmonary hypertension].
2001 Jun
Risk factors for pulmonary arterial hypertension.
2001 Sep
Effects of anorexinogen agents on cloned voltage-gated K(+) channel hKv1.5.
2001 Sep
Anorexigen-induced pulmonary hypertension and the serotonin (5-HT) hypothesis: lessons for the future in pathogenesis.
2002
[Pulmonary hypertension and obesity].
2002 Apr
Therapeutic and adverse actions of serotonin transporter substrates.
2002 Jul
Appetite suppressants as agonist substitution therapies for stimulant dependence.
2002 Jun
Effects on serotonin in rat hypothalamus of D-fenfluramine, aminorex, phentermine and fluoxetine.
2002 Jun 7
A century of pulmonary hemodynamics.
2004 Jul 15
Primary pulmonary arterial hypertension: a look back.
2004 Jun 16
Safety of drug therapies used for weight loss and treatment of obesity.
2006
Effects on weight reduction and safety of short-term phentermine administration in Korean obese people.
2006 Oct 31
Pharmacokinetics and effects of aminorex in horses.
2008 May
Pulmonary hypertension: therapeutic targets within the serotonin system.
2008 Oct
Review paper: Current strategies in the development of anti-obesity drugs and their safety concerns.
2009 Jan
The serotonin hypothesis of pulmonary hypertension revisited.
2010
Pulmonary hypertension associated with use of phentermine.
2010 Nov
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:53:17 GMT 2023
Edited
by admin
on Fri Dec 15 16:53:17 GMT 2023
Record UNII
WSK05IH80K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMINOREX FUMARATE
MI   WHO-DD  
Common Name English
2-OXAZOLAMINE, 4,5-DIHYDRO-5-PHENYL-, (E)-2-BUTENEDIOATE (1:1)
Systematic Name English
AMINOREX FUMARATE [MI]
Common Name English
Aminorex fumarate [WHO-DD]
Common Name English
Code System Code Type Description
MERCK INDEX
m1742
Created by admin on Fri Dec 15 16:53:17 GMT 2023 , Edited by admin on Fri Dec 15 16:53:17 GMT 2023
PRIMARY Merck Index
EVMPD
SUB00466MIG
Created by admin on Fri Dec 15 16:53:17 GMT 2023 , Edited by admin on Fri Dec 15 16:53:17 GMT 2023
PRIMARY
FDA UNII
WSK05IH80K
Created by admin on Fri Dec 15 16:53:17 GMT 2023 , Edited by admin on Fri Dec 15 16:53:17 GMT 2023
PRIMARY
CAS
16422-62-1
Created by admin on Fri Dec 15 16:53:17 GMT 2023 , Edited by admin on Fri Dec 15 16:53:17 GMT 2023
NON-SPECIFIC STOICHIOMETRY
SMS_ID
100000085177
Created by admin on Fri Dec 15 16:53:17 GMT 2023 , Edited by admin on Fri Dec 15 16:53:17 GMT 2023
PRIMARY
CAS
13425-22-4
Created by admin on Fri Dec 15 16:53:17 GMT 2023 , Edited by admin on Fri Dec 15 16:53:17 GMT 2023
PRIMARY
PUBCHEM
6433577
Created by admin on Fri Dec 15 16:53:17 GMT 2023 , Edited by admin on Fri Dec 15 16:53:17 GMT 2023
PRIMARY
MESH
C006559
Created by admin on Fri Dec 15 16:53:17 GMT 2023 , Edited by admin on Fri Dec 15 16:53:17 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY