List of aminorex analogues

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This is a list of aminorex analogues. Aminorex itself is a stimulant drug with a 5-phenyl-2-amino-oxazoline structure. It was developed in the 1960s as an anorectic,[1][2][3] but withdrawn from sale after it was discovered that extended use produced pulmonary hypertension, often followed by heart failure, which resulted in a number of deaths.[4] 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.[5][6][7][8] Pemoline, the 4-keto derivative of aminorex, had been discovered several years earlier,[9] and derivatives of this type appeared to be effective stimulants with comparatively low toxicity.[10][11] Pemoline was sold for around 25 years as a therapy for ADHD and relief of fatigue, before being withdrawn from the market in 2005 because of rare but serious cases of liver failure.[12][13][14][15] More recently in around 2014 another derivative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.[16][17][18] A number of related compounds are known, and new derivatives have continued to appear on the designer drug market.[19][20][21][22][23][24]

List of substituted aminorex derivatives[edit]

Structure Common name Chemical name CAS number
Aminorex structure.svg Aminorex 5-phenyl-4,5-dihydro-1,3-oxazol-2-amine 2207-50-3
Rexamino structure.png Rexamino 4-phenyl-4,5-dihydro-1,3-oxazol-2-amine 52883-35-9
4-fluoroaminorex structure.png 4'-Fluoroaminorex (4'-FAR) 5-(4-fluorophenyl)-4,5-dihydro-1,3-oxazol-2-amine 2967-77-3
Clominorex structure.svg Clominorex 5-(4-chlorophenyl)-4,5-dihydro-1,3-oxazol-2-amine 3876-10-6
Fluminorex.svg Fluminorex 5-[4-(trifluoromethyl)phenyl]-4,5-dihydro-1,3-oxazol-2-amine 720-76-3
2CB-AR structure.png 2C-B-aminorex (2C-B-AR) 5-(2,5-dimethoxy-4-bromophenyl)-4,5-dihydro-1,3-oxazol-2-amine
NN-DMAR structure.png N,N-Dimethylaminorex (N,N-DMAR) N,N-dimethyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine 32968-41-5
Pemoline structure 2.svg Pemoline 2-amino-5-phenyl-1,3-oxazol-4(5H)-one 2152-34-3
Thozalinone.svg Thozalinone 2-(dimethylamino)-5-phenyl-1,3-oxazol-4(5H)-one 655-05-0
Fenozolone.svg Fenozolone 2-ethylamino-5-phenyl-1,3-oxazol-4-one 15302-16-6
Cyclazodone structure.svg Cyclazodone 2-(cyclopropylamino)-5-phenyl-1,3-oxazol-4-one 14461-91-7
3-methylaminorex structure.png 3-Methylaminorex 3-methyl-5-phenyl-2-oxazolidinimine 75343-73-6
4-Methyl-Aminorex.svg 4-Methylaminorex (4-MAR) 4-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine 3568-94-3
4EAR structure.png 4-Ethylaminorex (4-EAR) 4-ethyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine 1364933-63-0
4N-DMAR structure.png 4,N-Dimethylaminorex (4,N-DMAR) 4,5-dihydro-N,4-dimethyl-5-phenyl-2-oxazolamine 2207-49-0
34-DMAR structure.png 3,4-Dimethylaminorex (3,4-DMAR) 3,4-dimethyl-5-phenyl-2-oxazolidinimine 82485-31-2
4,4'-Dimethylaminorex.svg 4,4'-Dimethylaminorex (4,4'-DMAR) 4-methyl-5-(4-methylphenyl)-4,5-dihydro-1,3-oxazol-2-amine 1445569-01-6
3F-4MAR structure.png 3'-Fluoro-4-methylaminorex (3'-F-4-MAR) 4-methyl-5-(3-fluorophenyl)-4,5-dihydro-1,3-oxazol-2-amine
4F-4MAR structure.png 4'-Fluoro-4-methylaminorex (4'-F-4-MAR) 4-methyl-5-(4-fluorophenyl)-4,5-dihydro-1,3-oxazol-2-amine 1364933-64-1
4MEO-4MAR structure.png 4'-Methoxy-4-methylaminorex (4'-MeO-4-MAR) 4-methyl-5-(4-methoxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine 1445570-65-9
345TM-4MAR structure.png 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
MD4MAR structure.png 3',4'-Methylenedioxy-4-methylaminorex (3',4'-MD-4-MAR) 4-methyl-5-(3,4-methylenedioyphenyl)-4,5-dihydro-1,3-oxazol-2-amine 1445573-16-9

See also[edit]

References[edit]

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  2. ^ Poos GI. 2-amino-5-aryloxazoline products. US Patent 3161650, 1962
  3. ^ Poos GI, Carson JR, Rosenau JD, Roszowski AP, Kelley NM, McGowin J (May 1963). "2-Amino-5-aryl-2-oxazolines. Potent New Anorectic Agents". Journal of Medicinal Chemistry. 6 (3): 266–272. doi:10.1021/jm00339a011. PMID 14185981.
  4. ^ Gurtner HP. Aminorex and pulmonary hypertension. A review. Cor Vasa. 1985;27(2-3):160-71. PMID 3928246
  5. ^ Davis FT, Brewster ME. A fatality involving U4Euh, a cyclic derivative of phenylpropanolamine. J Forensic Sci. 1988 Mar;33(2):549-53. PMID 3373171
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  9. ^ Schmidt L, Scheffler H. Central nervous system stimulant. US Patent 2892753, 1957
  10. ^ Hardy RA, Howell CF, Quinones NQ. Method of producing central nervous system stimulation and anorexia. US Patent 3313688, 1964
  11. ^ Guidicelli DP, Najer H. 5-phenyl-2-cyclopropylamino-4-oxazolinone, and process for making the same. US Patent 3609159, 1967
  12. ^ Marotta PJ, Roberts EA. Pemoline hepatotoxicity in children. J Pediatr. 1998 May;132(5):894-7. PMID 9602211
  13. ^ Safer DJ, Zito JM, Gardner JE. Pemoline hepatotoxicity and postmarketing surveillance. J Am Acad Child Adolesc Psychiatry. 2001 Jun;40(6):622-9. PMID 11392339
  14. ^ Etwel FA, Rieder MJ, Bend JR, Koren G (2008). "A surveillance method for the early identification of idiosyncratic adverse drug reactions". Drug Saf. 31 (2): 169–80. doi:10.2165/00002018-200831020-00006. PMID 18217792.
  15. ^ Shader RI. Risk Evaluation and Mitigation Strategies (REMS), Pemoline, and What Is a Signal? Clin Ther. 2017 Apr;39(4):665-669. . doi:10.1016/j.clinthera.2017.03.008. PMID 28366595. Cite journal requires |journal= (help); Missing or empty |title= (help)
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  17. ^ Coppola M, Mondola R. 4,4'-DMAR: chemistry, pharmacology and toxicology of a new synthetic stimulant of abuse. Basic Clin Pharmacol Toxicol. 2015 Jul;117(1):26-30. doi:10.1111/bcpt.12399 PMID 25819702
  18. ^ Maier J, Mayer FP, Luethi D, Holy M, Jäntsch K, Reither H, Hirtler L, Hoener MC, Liechti ME, Pifl C, Brandt SD, Sitte HH. The psychostimulant (±)-cis-4,4'-dimethylaminorex (4,4'-DMAR) interacts with human plasmalemmal and vesicular monoamine transporters. Neuropharmacology. 2018 Aug;138:282-291. doi:10.1016/j.neuropharm.2018.06.018 PMID 29908239
  19. ^ Russell BR, Beresford RA, Schmierer DM, McNaughton N, Clark CR. Stimulus properties of some analogues of 4-methylaminorex. Pharmacol Biochem Behav. 1995 Jun-Jul;51(2-3):375-8. PMID 7667356
  20. ^ Zheng Y, Russell B, Schmierer D, Laverty R. The effects of aminorex and related compounds on brain monoamines and metabolites in CBA mice. J Pharm Pharmacol. 1997 Jan;49(1):89-96. PMID 9120777
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