Systematic (IUPAC) name
Clinical data
Pregnancy cat.  ?
Legal status Schedule III (CA) Schedule I (US)
CAS number 2207-50-3
ATC code None
PubChem CID 16630
DrugBank DB01490
ChemSpider 15767 YesY
UNII 2SH16612I9 YesY
KEGG D02909 YesY
Chemical data
Formula C9H10N2O 
Mol. mass 162.19
SMILES eMolecules & PubChem
 YesY(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[1]. 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.[2] The drug has been retired from the market after it was found to result in pulmonary hypertension.[3]



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 It was introduced as a prescription appetite suppressant in Germany, Switzerland and Austria in 1965, but was withdrawn in 1972 after it was found to cause pulmonary hypertension in approximately 0.2% of patients, and was linked to a number of deaths.[2]


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).[4] A similar synthesis has been also published.[5]

Aminorex rxn mech.gif

See also


  1. ^ US Patent 3161650 - 2-Amino-5-Aryloxazoline Products
  2. ^ a b Fishman AP. (Jan 1991). "Aminorex to fen/phen - An epidemic foretold". Circulation 99 (1): 156–161. ISSN 0009-7322. PMID 9884392. 
  3. ^ Gaine SP, Rubin LJ, Kmetzo JJ, Palevsky HI, Traill TA (November 2000). "Recreational use of aminorex and pulmonary hypertension". Chest 118 (5): 1496–7. doi:10.1378/chest.118.5.1496. PMID 11083709. 
  4. ^ Poos GI, Carson JR, Rosenau JD, Roszowski AP, Kelley NM, McGowin J. (May 1963). "2-Amino-5-aryl-2-oxazolines. Potent New Anorectic Agents.". J. Med. Chem 6 (3): 266–272. doi:10.1021/jm00339a011. PMID 14185981. 
  5. ^ Ueda S, Terauchi H, Yano A, Ido M, Matsumoto M, Kawasaki M. (Jan 2004). "4,5-Disubstituted-1,3-oxazolidin-2-imine derivatives: a new class of orally bioavailable nitric oxide synthase inhibitor.". Bioorg. Med. Chem. Lett. 14 (2): 313–316. doi:10.1016/j.bmcl.2003.11.010. PMID 14698148. 

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Look at other dictionaries:

  • aminorex — noun An anorectic stimulant drug of the 2 amino 5 aryl oxazoline class …   Wiktionary

  • aminorex — A sympathomimetic appetite suppressant. * * * amin·o·rex (ə minґo reks) an amphetamine lying midway between dextroamphetamine and methamphetamine in central nervous system–stimulating effect and having anorectic actions; it has been a drug …   Medical dictionary

  • 4-Methyl-aminorex — Drugbox IUPAC name = 4 methyl 5 phenyl 2 amino oxazoline CAS number = 3568 94 3 CAS supplemental = 29493 77 4 (±) cis isomers ATC prefix= ATC suffix= ATC supplemental= PubChem= smiles = C1=CC=CC(=C1)C2C(N=C(O2)N)C DrugBank= C=10 | H=12 | N=2 |… …   Wikipedia

  • 4-Methylaminorex — Systematic (IUPAC) name 4 Methyl 5 phenyl 2 amino …   Wikipedia

  • Chlorphentermine — Systematic (IUPAC) name 1 (4 chlorophenyl) 2 methylpropan 2 amine Clinical data Pregnancy cat.  ? …   Wikipedia

  • Mazindol — Systematic (IUPAC) name (±) 5 (4 chlorophenyl) 3,5 dihydro 2H imidazo[2,1 a]isoindol 5 ol Clinical data AHFS/ …   Wikipedia

  • D-161 — Systematic (IUPAC) name 4 ((((3S,6S) 6 benzhydryltetrahydro 2H pyran 3 yl)amino)methyl)phenol Clinical data Pregnancy cat …   Wikipedia

  • Difemetorex — Systematic (IUPAC) name 2 [2 (diphenylmethyl)piperidin 1 yl]ethanol Clinical data Pregnancy cat.  ? …   Wikipedia

  • Metamfepramone — Systematic (IUPAC) name (RS) 2 dimethylamino 1 phenylpropan 1 one Clinical data Pregnancy cat. &# …   Wikipedia

  • Tranylcypromine — Systematic (IUPAC) name (±) trans 2 phenylcyclopropan 1 amine or (1R*,2S*) 2 phenylcyclopropan 1 amine …   Wikipedia

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