Fenproporex

Title: Fenproporex
CAS Registry Number: 15686-61-0
CAS Name: 3-[(1-Methyl-2-phenylethyl)amino]propanenitrile
Additional Names: (±)-3-[(a-methylphenethyl)amino]propionitrile; (±)-N-2-cyanoethylamphetamine
Molecular Formula: C12H16N2
Molecular Weight: 188.27
Percent Composition: C 76.55%, H 8.57%, N 14.88%
Literature References: Deriv of amphetamine, q.v. Prepn: FR M4364; P. Pohrbach, J. Blum, US 3485924 (1966, 1969 both to Bottu). Pharmacological studies: B. M. Beecham et al., J. Pharm. Pharmacol. 23, 140 (1971); A. H. Beckett et al., ibid. 24, 194 (1972). Peripheral effects in human and rat adipose tissue: M. Dubost et al., Br. J. Pharmacol. 58, 436P (1976). Chromatographic identification of amphetamine in urine of patients treated with fenproporex: R. B. Sznelvar, Eur. J. Toxicol. Environ. Hyg. 8, 5 (1975). Clinical trial: G. Hertel, W. Fallot-Burghardt, Fortschr. Med. 96, 2380 (1978).
Properties: Liquid, bp2 126-127°.
Boiling point: bp2 126-127°
Derivative Type: Hydrochloride
CAS Registry Number: 18305-29-8
Trademarks: Gacilin (Andromaco); Solvolip (Knoll)
Molecular Formula: C12H16N2.HCl
Molecular Weight: 224.73
Percent Composition: C 64.13%, H 7.62%, N 12.47%, Cl 15.78%
Properties: White, cryst, odorless powder from abs ethanol, mp 146°. Bitter taste. Sol in water, 95% ethanol.
Melting point: mp 146°
NOTE: This is a controlled substance (stimulant): 21 CFR, 1308.14.
Therap-Cat: Anorexic.
Keywords: Anorexic.
Fenprostalene Fenpyroximate Fenquizone Fenspiride Fensulfothion

Fenproporex
Fenproporex.svg
Systematic (IUPAC) name
3-(1-phenylpropan-2-ylamino)propanenitrile
Clinical data
AHFS/Drugs.com International Drug Names
Legal status Schedule IV (US)
Routes oral[1]
Pharmacokinetic data
Metabolism partly converted to amphetamine (30 to 60%)[1]
Excretion urine, mainly as amphetamine, about 5 to 9% unchanged[1]
Identifiers
CAS number 16397-28-7
ATC code None
PubChem CID 61810
DrugBank DB01550
ChemSpider 55690 YesY
UNII W0194S5FOA YesY
KEGG D07947 YesY
Chemical data
Formula C12H16N2 
Mol. mass 188.269
 YesY (what is this?)  (verify)

Fenproporex (Perphoxene) is a stimulant drug of the phenethylamine and amphetamine chemical classes which was developed in the 1960s. It is used as an appetite suppressant for the treatment of obesity.[2]

Fenproporex produces amphetamine as a metabolite,[3][4] and was withdrawn in many countries following problems with abuse,[5] but it is still prescribed in some countries. It is sometimes combined with benzodiazepines, antidepressants and other compounds to create the "Brazilian diet pill".[6][7]

Fenproporex has never been approved by the US Food and Drug Administration (FDA) for sale in the US due to lack of efficacy and safety data. However, in March 2009 the FDA warned consumers that it has been detected as an unlabeled component of diet pills available over the Internet.[8] Fenproporex is designated a Schedule IV controlled substance in the US pursuant to the Controlled Substances Act.[9]

Fenproporex is on the list of substances banned by the World Anti-Doping Agency, and any sportsperson testing positive for the substance faces a ban from competition.[10]