This is a list of aminorex analogues, also known as substituted 2-amino-5-aryloxazolines. Aminorex itself is a stimulant drug with a 5-phenyl-2-amino-oxazoline structure. It was developed in the 1960s as an anorectic,Meschino JA, Poos GI. 2-amino-5,6-dihydro-4H-1,3-oxazines and a process for their preparation. US Patent 3115494, 1961Poos GI. 2-amino-5-aryloxazoline products. US Patent 3161650, 1962 but withdrawn from sale after it was discovered that extended use produced pulmonary hypertension, often followed by heart failure, which resulted in a number of deaths. A designer drug analogue 4-methylaminorex appeared on the illicit market in the late 1980s but did not attract significant popularity due to its steep dose-response curve and tendency to produce seizures. Pemoline, the 4-keto derivative of aminorex, had been discovered several years earlier,Schmidt L, Scheffler H. Central nervous system stimulant. US Patent 2892753, 1957 and derivatives of this type appeared to be effective stimulants with comparatively low toxicity. Pemoline was sold for around 25 years as a therapy for ADHD and relief of fatigue, before being withdrawn from the market in 2005 because of rare but serious cases of liver failure. More recently in around 2014 another derivative 4,4'-dimethylaminorex started to be sold illicitly, but again swiftly lost popularity due to a spate of fatal overdose cases. A number of related compounds are known, and new derivatives have continued to appear on the designer drug market.
List of substituted aminorex derivatives
Structure Common name Chemical name CAS # 5-Phenyl-2-oxazoline 5-phenyl-4,5-dihydro-1,3-oxazole ? Aminorex 5-phenyl-4,5-dihydro-1,3-oxazol-2-amine 2207-50-3 Rexamino 4-phenyl-4,5-dihydro-1,3-oxazol-2-amine 52883-35-9 4'-Fluoroaminorex (4'-FAR) 5-(4-fluorophenyl)-4,5-dihydro-1,3-oxazol-2-amine 2967-77-3 Clominorex 5-(4-chlorophenyl)-4,5-dihydro-1,3-oxazol-2-amine 3876-10-6 Fluminorex 5-[4-(trifluoromethyl)phenyl]-4,5-dihydro-1,3-oxazol-2-amine 720-76-3 Methylenedioxyaminorex 5-(3,4-methylenedioxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine 3865-98-3 2C-B-aminorex (2C-B-AR) 5-(2,5-dimethoxy-4-bromophenyl)-4,5-dihydro-1,3-oxazol-2-amine N,N-Dimethylaminorex (N,N-DMAR) N,N-dimethyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine 32968-41-5 Pemoline 2-amino-5-phenyl-1,3-oxazol-4(5H)-one 2152-34-3 Thozalinone 2-(dimethylamino)-5-phenyl-1,3-oxazol-4(5H)-one 655-05-0 3F-Thozalinone 2-(dimethylamino)-5-(3-fluorophenyl)-1,3-oxazol-4(5H)-one Fenozolone 2-ethylamino-5-phenyl-1,3-oxazol-4-one 15302-16-6 Cyclazodone 2-(cyclopropylamino)-5-phenyl-1,3-oxazol-4-one 14461-91-7 N-Methylcyclazodone 2-(cyclopropyl(methyl)amino)-5-phenyl-1,3-oxazol-4-one 14461-92-8 Ephedroxane (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one 16251-46-0 3-Methylaminorex 3-methyl-5-phenyl-2-oxazolidinimine 75343-73-6 4-Methylaminorex (4-MAR) 4-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine 3568-94-3 4-Ethylaminorex (4-EAR) 4-ethyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine 1364933-63-0 4-Isopropylaminorex 4-isopropyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine 4-Isobutylaminorex 4-(2-methylpropyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine 4-tert-butylaminorex 4-(1,1-dimethylethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine 4,N-Dimethylaminorex (4,N-DMAR) 4,5-dihydro-N,4-dimethyl-5-phenyl-2-oxazolamine 2207-49-0 3,4-Dimethylaminorex (3,4-DMAR) 3,4-dimethyl-5-phenyl-2-oxazolidinimine 82485-31-2 4,4'-Dimethylaminorex (4,4'-DMAR) 4-methyl-5-(4-methylphenyl)-4,5-dihydro-1,3-oxazol-2-amine 1445569-01-6 2'-Fluoro-4-methylaminorex (2F-MAR) 4-methyl-5-(2-fluorophenyl)-4,5-dihydro-1,3-oxazol-2-amine 3'-Fluoro-4-methylaminorex (3F-MAR) 4-methyl-5-(3-fluorophenyl)-4,5-dihydro-1,3-oxazol-2-amine 4'-Fluoro-4-methylaminorex (4F-MAR) 4-methyl-5-(4-fluorophenyl)-4,5-dihydro-1,3-oxazol-2-amine 1364933-64-1 4'-Chloro-4-methylaminorex (4C-MAR) 4-methyl-5-(4-chlorophenyl)-4,5-dihydro-1,3-oxazol-2-amine 4'-Bromo-4-methylaminorex (4B-MAR) 4-methyl-5-(4-bromophenyl)-4,5-dihydro-1,3-oxazol-2-amine 4'-Methoxy-4-methylaminorex (4'-MeO-4-MAR) 4-methyl-5-(4-methoxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine 1445570-65-9 3',4',5'-Trimethoxy-4-methylaminorex (TM-4-MAR) 4-methyl-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine 1445571-92-5 3',4'-Methylenedioxy-4-methylaminorex (MDMAR) 4-methyl-5-(3,4-methylenedioyphenyl)-4,5-dihydro-1,3-oxazol-2-amine 1445573-16-9
See also Berefrine RO5166017 List of methylphenidate analogues Substituted benzofuran Substituted cathinone Substituted phenylmorpholine
References