Aminorex
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Aminorex
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| 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  |
| UNII | 2SH16612I9 |
| KEGG | D02909 |
| ChEMBL | CHEMBL106258 |
| Chemical data | |
| Formula | C9H10N2O |
| Mol. mass | 162.19 |
| SMILES | eMolecules & PubChem |
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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]
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Contents
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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 It was introduced as a prescription appetite suppressant in Germany, Switzerland and Austria in 1965, but was withdrawn in 1972 after it was found to cause pulmonary hypertension in approximately 0.2% of patients, and was linked to a number of deaths.[2]
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).[4] A similar synthesis has been also published.[5]
See also
References
- ^ US Patent 3161650 - 2-Amino-5-Aryloxazoline Products
- ^ a b Fishman AP. (Jan 1991). "Aminorex to fen/phen - An epidemic foretold". Circulation 99 (1): 156–161. ISSN 0009-7322. PMID 9884392.
- ^ 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. http://www.chestjournal.org/cgi/pmidlookup?view=long&pmid=11083709.
- ^ 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.
- ^ 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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