AMINOREX

Details

Stereochemistry	RACEMIC
Molecular Formula	C9H10N2O
Molecular Weight	162.1885
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NCC(O1)C2=CC=CC=C2

InChI

InChIKey=SYAKTDIEAPMBAL-UHFFFAOYSA-N

InChI=1S/C9H10N2O/c10-9-11-6-8(12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H2,10,11)

HIDE SMILES / InChI

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Germany, and Austria, but was found to cause pronounced vasoconstriction in the pulmonary vasculature, and was withdrawn from the market in 1972 due to several cases of fatal and life-threatening pulmonary hypertension.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
Pulmonary hypertension associated with use of phentermine.	2010-11	20879069
Levamisole: a dangerous new cocaine adulterant.	2010-09	20668440
The serotonin hypothesis of pulmonary hypertension revisited.	2010	20204739
Aminorex and rexamino as metabolites of levamisole in the horse.	2009-04-06	19298880
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.	2009-04	19290946
Review paper: Current strategies in the development of anti-obesity drugs and their safety concerns.	2009-01	19112110
Pulmonary hypertension: therapeutic targets within the serotonin system.	2008-10	18536742
Converging evidence in support of the serotonin hypothesis of dexfenfluramine-induced pulmonary hypertension with novel transgenic mice.	2008-06-03	18506000
Pharmacokinetics and effects of aminorex in horses.	2008-05	18447801
Effects on weight reduction and safety of short-term phentermine administration in Korean obese people.	2006-10-31	17066505
Temporal trends and drug exposures in pulmonary hypertension: an American experience.	2006-09	16923424
Safety of drug therapies used for weight loss and treatment of obesity.	2006	16569079
A century of pulmonary hemodynamics.	2004-07-15	15242851
Primary pulmonary arterial hypertension: a look back.	2004-06-16	15194172
Noradrenergic modulation of ephedrine-induced hypophagia.	2003-04	12557268
Therapeutic and adverse actions of serotonin transporter substrates.	2002-07	12163129
Effects on serotonin in rat hypothalamus of D-fenfluramine, aminorex, phentermine and fluoxetine.	2002-06-07	12065196
Appetite suppressants as agonist substitution therapies for stimulant dependence.	2002-06	12105089
[Pulmonary hypertension and obesity].	2002-04	12082449
Anorexigen-induced pulmonary hypertension and the serotonin (5-HT) hypothesis: lessons for the future in pathogenesis.	2002	11806844
Risk factors for pulmonary arterial hypertension.	2001-09	11590841
Effects of anorexinogen agents on cloned voltage-gated K(+) channel hKv1.5.	2001-09	11504808
[Drug induced pulmonary hypertension].	2001-06	11411136
Anorectic drugs and pulmonary hypertension from the bedside to the bench.	2001-04	11307870
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.	2001-01	11071707
[Obesity: principles of drug therapy].	2000-08	11026090
[Anorectics and pulmonary hypertension].	2000-02-16	10838744
[Development of pulmonary hypertension and multi-valvular damage caused by appetite depressants].	1998-12-01	10911459
Monoclonal endothelial cells in appetite suppressant-associated pulmonary hypertension.	1998-12	9847298
Two different drug-induced pulmonary complications in a patient suffering from rheumatoid arthritis.	1998-05	9651097
Aminorex, dexfenfluramine, and primary pulmonary hypertension.	1998-04	9539893
Pulmonary hypertension and dexfenfluramine.	1995	7621854
[A case of chronic pulmonary hypertension after fenfluramine intake].	1982-11-26	7164466

Name

Type

Language

APIQUEL

Preferred Name

English

AMINOREX

Official Name

English

AMINOREX [MI]

Common Name

English

aminorex [INN]

Common Name

English

(±)-2-AMINO-5-PHENYL-2-OXAZOLINE

Systematic Name

English

2-Amino-5-phenyl-2-oxazoline

Systematic Name

English

MCN-742

Code

English

AMINOREX [HSDB]

Common Name

English

NSC-66952

Code

English

2-OXAZOLAMINE, 4,5-DIHYDRO-5-PHENYL-

Systematic Name

English

Aminorex [WHO-DD]

Common Name

English

AMINOREX [MART.]

Common Name

English

AMINOREX [USAN]

Common Name

English

Classification Tree Code System Code

DEA NO.

1585