Aminorex

Aminorex

Systematic (IUPAC) name
(RS)-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine
Clinical data
Pregnancy cat.	?
Legal status	Schedule III (CA) Schedule I (US)
Identifiers
CAS number	2207-50-3
ATC code	None
PubChem	CID 16630
DrugBank	DB01490
ChemSpider	15767 Y
UNII	2SH16612I9 Y
KEGG	D02909 Y
ChEMBL	CHEMBL106258 Y
Chemical data
Formula	C9H10N2O
Mol. mass	162.19
SMILES	eMolecules & PubChem
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
Y(what is this?)  (verify)

Aminorex (Menocil, Apiquel, aminoxaphen, aminoxafen, McN-742) is an anorectic stimulant drug of the 2-amino-5-aryl oxazoline class developed by a team at 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. The drug has been retired from the market after it was found to result in pulmonary hypertension.

History

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 It was introduced as a prescription appetite suppressant in Germany, Switzerland and Austria in 1965, but was withdrawn in 1972 after it was found to cause pulmonary hypertension in approximately 0.2% of patients, and was linked to a number of deaths.

Synthesis

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. This racemic synthesis involved an addition/cyclization reaction of 2-amino-1-phenylethanol with cyanogen bromide (mechanism shown below). A similar synthesis has been also published.

See also

• 4-Methylaminorex
• Clominorex
• Cyclazodone
• Fenozolone
• Fluminorex
• Pemoline
• Thozalinone