AMINOREX FUMARATE

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 Search

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

Description
Sources: https://thorax.bmj.com/content/26/3/262.abstract | https://www.ncbi.nlm.nih.gov/pubmed/24296074 | https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+7596

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Germany, and Austria, but was found to cause pronounced vasoconstriction in the pulmonary vasculature, and was withdrawn from the market in 1972 due to several cases of fatal and life-threatening pulmonary hypertension.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

Title	Date	PubMed
[A case of chronic pulmonary hypertension after fenfluramine intake].	1982 Nov 26	7164466
Pulmonary hypertension and dexfenfluramine.	1995	7621854
Aminorex, dexfenfluramine, and primary pulmonary hypertension.	1998 Apr	9539893
Monoclonal endothelial cells in appetite suppressant-associated pulmonary hypertension.	1998 Dec	9847298
[Development of pulmonary hypertension and multi-valvular damage caused by appetite depressants].	1998 Dec 1	10911459
Two different drug-induced pulmonary complications in a patient suffering from rheumatoid arthritis.	1998 May	9651097
[Obesity: principles of drug therapy].	2000 Aug	11026090
[Anorectics and pulmonary hypertension].	2000 Feb 16	10838744
Anorectic drugs and pulmonary hypertension from the bedside to the bench.	2001 Apr	11307870
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.	2001 Jan	11071707
[Drug induced pulmonary hypertension].	2001 Jun	11411136
Risk factors for pulmonary arterial hypertension.	2001 Sep	11590841
Effects of anorexinogen agents on cloned voltage-gated K(+) channel hKv1.5.	2001 Sep	11504808
Anorexigen-induced pulmonary hypertension and the serotonin (5-HT) hypothesis: lessons for the future in pathogenesis.	2002	11806844
[Pulmonary hypertension and obesity].	2002 Apr	12082449
Therapeutic and adverse actions of serotonin transporter substrates.	2002 Jul	12163129
Appetite suppressants as agonist substitution therapies for stimulant dependence.	2002 Jun	12105089
Effects on serotonin in rat hypothalamus of D-fenfluramine, aminorex, phentermine and fluoxetine.	2002 Jun 7	12065196
Noradrenergic modulation of ephedrine-induced hypophagia.	2003 Apr	12557268
A century of pulmonary hemodynamics.	2004 Jul 15	15242851
Primary pulmonary arterial hypertension: a look back.	2004 Jun 16	15194172
Safety of drug therapies used for weight loss and treatment of obesity.	2006	16569079
Effects on weight reduction and safety of short-term phentermine administration in Korean obese people.	2006 Oct 31	17066505
Temporal trends and drug exposures in pulmonary hypertension: an American experience.	2006 Sep	16923424
Converging evidence in support of the serotonin hypothesis of dexfenfluramine-induced pulmonary hypertension with novel transgenic mice.	2008 Jun 3	18506000
Pharmacokinetics and effects of aminorex in horses.	2008 May	18447801
Pulmonary hypertension: therapeutic targets within the serotonin system.	2008 Oct	18536742
The formation of aminorex in racehorses following levamisole administration. A quantitative and chiral analysis following synthetic aminorex or levamisole administration vs. aminorex-positive samples from the field: a preliminary report.	2009 Apr	19290946
Aminorex and rexamino as metabolites of levamisole in the horse.	2009 Apr 6	19298880
Review paper: Current strategies in the development of anti-obesity drugs and their safety concerns.	2009 Jan	19112110
The serotonin hypothesis of pulmonary hypertension revisited.	2010	20204739
Pulmonary hypertension associated with use of phentermine.	2010 Nov	20879069
Levamisole: a dangerous new cocaine adulterant.	2010 Sep	20668440

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:53:17 UTC 2023` Edited by `admin` on `Fri Dec 15 16:53:17 UTC 2023`
Record UNII	WSK05IH80K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMINOREX FUMARATE

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