Fluminorex

Fluminorex
Clinical data
ATC code	none;
Identifiers
	IUPAC name (RS)-5-[4-(trifluoromethyl)phenyl]-4,5-dihydro-1,3-oxazol-2-amine;
CAS Number	720-76-3 ;
PubChem CID	24100;
ChemSpider	22530 ;
UNII	LUO2Z7954T;
KEGG	D04210 ;
ChEMBL	ChEMBL2107247;
CompTox Dashboard (EPA)	DTXSID00862387 ;
Chemical and physical data
Formula	C10H9F3N2O
Molar mass	230.190 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES FC(F)(F)c1ccc(cc1)C2O\C(=N/C2)N;
	InChI InChI=1S/C10H9F3N2O/c11-10(12,13)7-3-1-6(2-4-7)8-5-15-9(14)16-8/h1-4,8H,5H2,(H2,14,15) ; Key:NMGYDYBWRZHLHR-UHFFFAOYSA-N ;
	(verify)

Fluminorex is a centrally acting sympathomimetic which is related to other drugs such as aminorex and pemoline. It was developed as an appetite suppressant by McNeil Laboratories in the 1950s.^[1]^[2]

Synthesis

Synthesis:^[3] Patent (Ex XV):^[4]

2-amino-1-[4-(trifluoromethyl)phenyl]ethanol [776-02-3] (1) cyanogen bromide [506-68-3] (2)

^ US Patent 3278382 - 2-amino-5-aryloxazoline compositions and methods of using same
^ Maier J, Mayer FP, Brandt SD, Sitte HH (October 2018). "DARK Classics in Chemical Neuroscience: Aminorex Analogues". ACS Chemical Neuroscience. 9 (10): 2484–2502. doi:10.1021/acschemneuro.8b00415. PMC 6287711. PMID 30269490.
^ Poos, G. I., Carson, J. R., Rosenau, J. D., Roszkowski, A. P., Kelley, N. M., 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.
^ Poos George Ireland, U.S. patent 3,278,382 (1966 to Janssen Pharmaceuticals Inc).

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Clinical data

ATC code	none
Identifiers
IUPAC name (RS)-5-[4-(trifluoromethyl)phenyl]-4,5-dihydro-1,3-oxazol-2-amine
CAS Number	720-76-3^Y
PubChem CID	24100
ChemSpider	22530^Y
UNII	LUO2Z7954T
KEGG	D04210^Y
ChEMBL	ChEMBL2107247
CompTox Dashboard (EPA)	DTXSID00862387
Chemical and physical data
Formula	C₁₀H₉F₃N₂O
Molar mass	230.190 g·mol⁻¹
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES FC(F)(F)c1ccc(cc1)C2O\C(=N/C2)N
InChI InChI=1S/C10H9F3N2O/c11-10(12,13)7-3-1-6(2-4-7)8-5-15-9(14)16-8/h1-4,8H,5H2,(H2,14,15)^Y Key:NMGYDYBWRZHLHR-UHFFFAOYSA-N^Y
(verify)