Aminorex

Aminorex
Clinical data
Other names	Aminoxaphen; Aminoxafen; McN-742
ATC code	none;
Legal status
Legal status	BR: Class B2 (Anorectic drugs); CA: Schedule III; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class C; US: Schedule I;
Identifiers
	IUPAC name (RS)-5-Phenyl-4,5-dihydro-1,3-oxazol-2-amine;
CAS Number	2207-50-3 ;
PubChem CID	16630;
DrugBank	DB01490 ;
ChemSpider	15767 ;
UNII	2SH16612I9;
KEGG	D02909 ;
ChEMBL	ChEMBL106258 ;
CompTox Dashboard (EPA)	DTXSID00862867 ;
ECHA InfoCard	100.164.420
Chemical and physical data
Formula	C9H10N2O
Molar mass	162.192 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES NC1=NCC(C2=CC=CC=C2)O1;
	InChI InChI=1S/C9H10N2O/c10-9-11-6-8(12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H2,10,11) ; Key:SYAKTDIEAPMBAL-UHFFFAOYSA-N ;
	(verify)

Aminorex, sold under the brand names Menocil and Apiquel among others, is a weight loss (anorectic) stimulant drug.^[2]^[3] It was withdrawn from the market after it was found to cause pulmonary hypertension (PPH).^[3]^[4] In the United States, aminorex is a Schedule I controlled substance.

Aminorex, in the 2-amino-5-aryloxazoline group, was developed by McNeil Laboratories in 1962.^[5] It is closely related to 4-methylaminorex (4-MAR). 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.^[6] It can be produced as a metabolite of the deworming medication levamisole, which is sometimes used as a cutting agent of illicitly produced cocaine.^[7]^[8]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 54. ISBN 978-1-4757-2085-3. Retrieved 10 January 2025.
^ ^a ^b Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 14. ISBN 978-94-011-4439-1. Retrieved 10 January 2025.
^ Gaine SP, Rubin LJ, Kmetzo JJ, Palevsky HI, Traill TA (November 2000). "Recreational use of aminorex and pulmonary hypertension". Chest. 118 (5): 1496–1497. doi:10.1378/chest.118.5.1496. PMID 11083709. Archived from the original on 2013-01-12.
^ US 3161650, Ireland PG, "2-Amino-5-Aryloxazoline Products", issued 15 December 1964, assigned to Janssen Pharmaceuticals Inc.
^ Fishman AP (Jan 1991). "Aminorex to fen/phen: an epidemic foretold". Circulation. 99 (1): 156–161. doi:10.1161/01.CIR.99.1.156. PMID 9884392.
^ Ho EN, Leung DK, Leung GN, Wan TS, Wong AS, Wong CH, et al. (April 2009). "Aminorex and rexamino as metabolites of levamisole in the horse". Analytica Chimica Acta. 638 (1): 58–68. Bibcode:2009AcAC..638...58H. doi:10.1016/j.aca.2009.02.033. PMID 19298880.
^ Bertol E, Mari F, Milia MG, Politi L, Furlanetto S, Karch SB (July 2011). "Determination of aminorex in human urine samples by GC-MS after use of levamisole". Journal of Pharmaceutical and Biomedical Analysis. 55 (5): 1186–1189. doi:10.1016/j.jpba.2011.03.039. PMID 21531521.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[Elks2014-2] Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 54. ISBN 978-1-4757-2085-3. Retrieved 10 January 2025.

[MortonHall2012-3] Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 14. ISBN 978-94-011-4439-1. Retrieved 10 January 2025.

[pmid11083709-4] Gaine SP, Rubin LJ, Kmetzo JJ, Palevsky HI, Traill TA (November 2000). "Recreational use of aminorex and pulmonary hypertension". Chest. 118 (5): 1496–1497. doi:10.1378/chest.118.5.1496. PMID 11083709. Archived from the original on 2013-01-12.

[5] US 3161650, Ireland PG, "2-Amino-5-Aryloxazoline Products", issued 15 December 1964, assigned to Janssen Pharmaceuticals Inc.

[pmid9884392-6] Fishman AP (Jan 1991). "Aminorex to fen/phen: an epidemic foretold". Circulation. 99 (1): 156–161. doi:10.1161/01.CIR.99.1.156. PMID 9884392.

[7] Ho EN, Leung DK, Leung GN, Wan TS, Wong AS, Wong CH, et al. (April 2009). "Aminorex and rexamino as metabolites of levamisole in the horse". Analytica Chimica Acta. 638 (1): 58–68. Bibcode:2009AcAC..638...58H. doi:10.1016/j.aca.2009.02.033. PMID 19298880.

[pmid21531521-8] Bertol E, Mari F, Milia MG, Politi L, Furlanetto S, Karch SB (July 2011). "Determination of aminorex in human urine samples by GC-MS after use of levamisole". Journal of Pharmaceutical and Biomedical Analysis. 55 (5): 1186–1189. doi:10.1016/j.jpba.2011.03.039. PMID 21531521.

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Aminorex

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