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Substituted aminorexes

Original Wikipedia articleen.wikipedia.org/wiki/List_of_aminorex_analogues revision used (24 October 2026)

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Overview

Substituted aminorex refers to a chemical class of compounds that are based on the structure of aminorex. PW

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 It was developed in the 1960s as an anorectic, but withdrawn from sale after it was discovered that extended use produced pulmonary hypertension, often followed by heart failure, which resulted in a number of deaths.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, 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 Pemoline was sold for around 25 years as a therapy for ADHD and relief of fatigue, before being withdrawn from the market in 2005 because of rare but serious cases of liver failure.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.[1–24] WP

Drugs in this class on intoxicant.wiki

Every page on this site that a cited source puts in this class: 9 pages. A drug is listed when PsychonautWiki's "Substituted aminorexes" page, revision 144533 lists it, or when its own PsychonautWiki, TripSit or Wikipedia entry names this class. Each name opens our page for that drug; long chemical names are shown by a shorter name the drug is also known by (hover for the full name).

Tags show who puts each drug in this class (hover for the exact wording): PW list = listed on PsychonautWiki's page for this class; PW = the drug's PsychonautWiki entry; TS = the drug's TripSit entry (drug category); WP = the drug infobox of the drug's Wikipedia article. These are classifications only, not dosage guidance.

References

  1. Other Meschino JA, Poos GI. 2-amino-5,6-dihydro-4H-1,3-oxazines and a process for their preparation. US Patent 3115494, 1961
  2. Other Poos GI. 2-amino-5-aryloxazoline products. US Patent 3161650, 1962
  3. Journal / agency Poos GI, Carson JR, Rosenau JD, Roszkowski AP, Kelley NM, Mcgowin J. 2-Amino-5-aryl-2-oxazolines. Potent New Anorectic Agents. Journal of Medicinal Chemistry. May 1963. doi:10.1021/jm00339a011 · PMID 14185981
  4. Journal / agency Gurtner HP. Aminorex and pulmonary hypertension. A review. Cor et Vasa. 1985. PMID 3928246
  5. Journal / agency Davis FT, Brewster ME. A fatality involving U4Euh, a cyclic derivative of phenylpropanolamine. Journal of Forensic Sciences. March 1988. doi:10.1520/JFS11971J · PMID 3373171
  6. Journal / agency Bunker CF, Johnson M, Gibb JW, Bush LG, Hanson GR. Neurochemical effects of an acute treatment with 4-methylaminorex: a new stimulant of abuse. European Journal of Pharmacology. May 1990. doi:10.1016/0014-2999(90)90597-y · PMID 1973111
  7. Journal / agency Gaine SP, Rubin LJ, Kmetzo JJ, Palevsky HI, Traill TA. Recreational use of aminorex and pulmonary hypertension. Chest. November 2000. doi:10.1378/chest.118.5.1496 · PMID 11083709
  8. Journal / agency Meririnne E, Kajos M, Kankaanpää A, Koistinen M, Kiianmaa K, Seppälä T. Rewarding properties of the stereoisomers of 4-methylaminorex: involvement of the dopamine system. Pharmacology, Biochemistry, and Behavior. August 2005. doi:10.1016/j.pbb.2005.04.020 · PMID 15982727
  9. Other Schmidt L, Scheffler H. Central nervous system stimulant. US Patent 2892753, 1957
  10. Other Hardy RA, Howell CF, Quinones NQ. Method of producing central nervous system stimulation and anorexia. US Patent 3313688, 1964
  11. Other Guidicelli DP, Najer H. 5-phenyl-2-cyclopropylamino-4-oxazolinone, and process for making the same. US Patent 3609159, 1967
  12. Journal / agency Marotta PJ, Roberts EA. Pemoline hepatotoxicity in children. The Journal of Pediatrics. May 1998. doi:10.1016/s0022-3476(98)70329-4 · PMID 9602211
  13. Journal / agency Safer DJ, Zito JM, Gardner JE. Pemoline hepatotoxicity and postmarketing surveillance. Journal of the American Academy of Child and Adolescent Psychiatry. June 2001. doi:10.1097/00004583-200106000-00006 · PMID 11392339
  14. Journal / agency Etwel FA, Rieder MJ, Bend JR, Koren G. A surveillance method for the early identification of idiosyncratic adverse drug reactions. Drug Safety. 2008. doi:10.2165/00002018-200831020-00006 · PMID 18217792
  15. Journal / agency Shader RI. Risk Evaluation and Mitigation Strategies (REMS), Pemoline, and What Is a Signal?. Clinical Therapeutics. April 2017. doi:10.1016/j.clinthera.2017.03.008 · PMID 28366595
  16. Journal / agency Brandt SD, Baumann MH, Partilla JS, Kavanagh PV, Power JD, Talbot B, Twamley B, Mahony O, O'Brien J, Elliott SP, Archer RP, Patrick J, Singh K, Dempster NM, Cosbey SH. Characterization of a novel and potentially lethal designer drug (±)-cis-para-methyl-4-methylaminorex (4,4'-DMAR, or 'Serotoni'). Drug Testing and Analysis. 2014. doi:10.1002/dta.1668 · PMID 24841869 · PMC4128571
  17. Journal / agency Coppola M, Mondola R. 4,4'-DMAR: chemistry, pharmacology and toxicology of a new synthetic stimulant of abuse. Basic & Clinical Pharmacology & Toxicology. July 2015. doi:10.1111/bcpt.12399 · PMID 25819702
  18. Journal / agency 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. August 2018. doi:10.1016/j.neuropharm.2018.06.018 · PMID 29908239
  19. Journal / agency Russell BR, Beresford RA, Schmierer DM, McNaughton N, Clark CR. Stimulus properties of some analogues of 4-methylaminorex. Pharmacology, Biochemistry, and Behavior. 1995. doi:10.1016/0091-3057(94)00407-a · PMID 7667356
  20. Journal / agency Zheng Y, Russell B, Schmierer D, Laverty R. The effects of aminorex and related compounds on brain monoamines and metabolites in CBA mice. The Journal of Pharmacy and Pharmacology. January 1997. doi:10.1111/j.2042-7158.1997.tb06758.x · PMID 9120777
  21. Journal / agency McLaughlin G, Morris N, Kavanagh PV, Power JD, Twamley B, O'Brien J, Talbot B, Dowling G, Mahony O, Brandt SD, Patrick J, Archer RP, Partilla JS, Baumann MH. Synthesis, characterization, and monoamine transporter activity of the new psychoactive substance 3',4'-methylenedioxy-4-methylaminorex (MDMAR). Drug Testing and Analysis. July 2015. doi:10.1002/dta.1732 · PMID 25331619 · PMC5331736
  22. Journal / agency Maier J, Mayer FP, Brandt SD, Sitte HH. DARK Classics in Chemical Neuroscience: Aminorex Analogues. ACS Chemical Neuroscience. October 2018. doi:10.1021/acschemneuro.8b00415 · PMID 30269490 · PMC6287711
  23. Journal / agency Fabregat-Safont D, Carbón X, Ventura M, Fornís I, Hernández F, Ibáñez M. Characterization of a recently detected halogenated aminorex derivative: para-fluoro-4-methylaminorex (4'F-4-MAR). Scientific Reports. June 2019. doi:10.1038/s41598-019-44830-y · PMID 31165778 · PMC6549166
  24. Journal / agency Rickli A, Kolaczynska K, Hoener MC, Liechti ME. Pharmacological characterization of the aminorex analogs 4-MAR, 4,4'-DMAR, and 3,4-DMAR. Neurotoxicology. May 2019. doi:10.1016/j.neuro.2019.02.011 · PMID 30776375

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