Aminorex

Aminorex

Clinical data
ATC code	none
Legal status
Legal status	CA: Schedule III DE: Anlage II (Prohibited) UK: Class C US: Schedule I
Identifiers
IUPAC name (RS)-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine
CAS Number	2207-50-3 Y
PubChem (CID)	16630
DrugBank	DB01490 Y
ChemSpider	15767 Y
UNII	2SH16612I9 Y
KEGG	D02909 Y
ChEMBL	CHEMBL106258 Y
ECHA InfoCard	100.164.420
Chemical and physical data
Formula	C9H10N2O
Molar mass	162.19
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
SMILES NC1=NCC(C2=CC=CC=C2)O1
InChI InChI=1S/C9H10N2O/c10-9-11-6-8(12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H2,10,11) Y Key:SYAKTDIEAPMBAL-UHFFFAOYSA-N Y

Aminorex (Menocil, Apiquel, aminoxaphen, aminoxafen, McN-742) is a weight loss (anorectic) stimulant drug. It was withdrawn from the market after it was found to cause pulmonary hypertension. In the U.S., it is an illegal Schedule I drug, with no medical use and poor safety profile.

Aminorex, in the 2-amino-5-aryl oxazoline class, was developed by McNeil in 1962. It is closely related to 4-methylaminorex. Aminorex has been shown to have locomotor stimulant effects, lying midway between dextroamphetamine and methamphetamine. Aminorex effects have been attributed to the release of catecholamines.

It was discovered in 1962 by Edward John Hurlburt (U.S. Patent 3,115,494), and was quickly found in 1963 to have an anorectic effect in rats. It was introduced as a prescription appetite suppressant in Germany, Switzerland and Austria in 1965, but was withdrawn in 1972 after it was found to cause pulmonary hypertension in approximately 0.2% of patients, and was linked to a number of deaths.

The synthesis was first reported in a structure-activity relationship study of 2-amino-5-aryl-2-oxazolines, where aminorex was found to be approximately 2.5 times more potent than D-amphetamine sulfate in inducing anorexia in rats, and was also reported to have CNS stimulant effects.