Aminorex

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Aminorex
Aminorex structure.svg
Systematic (IUPAC) name
(RS)-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine
Clinical data
Legal status
Identifiers
CAS Number 2207-50-3 YesY
ATC code none
PubChem CID: 16630
DrugBank DB01490 YesY
ChemSpider 15767 YesY
UNII 2SH16612I9 YesY
KEGG D02909 YesY
ChEMBL CHEMBL106258 YesY
Chemical data
Formula C9H10N2O
Molecular mass 162.19
  • NC1=NCC(C2=CC=CC=C2)O1
  • InChI=1S/C9H10N2O/c10-9-11-6-8(12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H2,10,11) YesY
  • Key:SYAKTDIEAPMBAL-UHFFFAOYSA-N YesY
  (verify)

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 It was withdrawn from the market after it was found to cause pulmonary hypertension.[1] In the U.S., it is an illegal Schedule I drug, with no medical use and poor safety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.[2] 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.[3]

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 It was introduced as a prescription appetite suppressant in Germany, Switzerland and Austria in 1965, but was withdrawn in 1972 after it was found to cause pulmonary hypertension in approximately 0.2% of patients, and was linked to a number of deaths.[3]

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.

Aminorex rxn mech.png

The racemic synthesis involves addition/cyclization reaction of 2-amino-1-phenylethanol with cyanogen bromide.[4] A similar synthesis has been also published.[5]

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ US Patent 3161650 - 2-Amino-5-Aryloxazoline Products
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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