Fenproporex

Last updated
Fenproporex
Fenproporex.svg
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
By mouth [1]
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Metabolism partly converted to amphetamine (30 to 60%) [1]
Excretion urine, mainly as amphetamine, about 5 to 9% unchanged [1]
Identifiers
  • 3-(1-phenylpropan-2-ylamino)propanenitrile
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.036.752 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C12H16N2
Molar mass 188.274 g·mol−1
3D model (JSmol)
  • N#CCCNC(Cc1ccccc1)C
  • InChI=1S/C12H16N2/c1-11(14-9-5-8-13)10-12-6-3-2-4-7-12/h2-4,6-7,11,14H,5,9-10H2,1H3 Yes check.svgY
  • Key:IQUFSXIQAFPIMR-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Fenproporex (Perphoxene) (N-2-Cyanoethylamphetamine) (3-(1-phenylpropan-2-ylamino)propanenitrile) (3-[(1-Methyl-2-Phenylethyl)amino]propiononitrile) is a stimulant drug of the phenethylamine and amphetamine chemical classes that was developed in the 1960s. It is used as an appetite suppressant for the treatment of obesity. [3]

Fenproporex produces amphetamine as a metabolite [4] [5] and was withdrawn in many countries following problems with abuse, [6] but it is still prescribed in some countries. It is sometimes combined with benzodiazepines, antidepressants, and other compounds to create a version of the "rainbow diet pill". [7] [8] [9]

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. [10] Fenproporex is designated a Schedule IV controlled substance in the US pursuant to the Controlled Substances Act. [11]

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. [12]

Related Research Articles

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<span class="mw-page-title-main">Benzphetamine</span> Chemical compound

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<span class="mw-page-title-main">Cathine</span> Chemical compound

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<span class="mw-page-title-main">Anti-obesity medication</span> Class of pharmacological agents

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<span class="mw-page-title-main">Phenmetrazine</span> Chemical compound

Phenmetrazine is a stimulant drug first synthesized in 1952 and originally used as an appetite suppressant, but withdrawn from the market in the 1980s due to widespread abuse. It was initially replaced by its analogue phendimetrazine which functions as a prodrug to phenmetrazine, but now it is rarely prescribed, due to concerns of abuse and addiction. Chemically, phenmetrazine is a substituted amphetamine containing a morpholine ring.

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<span class="mw-page-title-main">Aminorex</span> Chemical compound

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<span class="mw-page-title-main">Dexfenfluramine</span> Serotonergic anorectic medication

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<span class="mw-page-title-main">Clobenzorex</span> Stimulant drug used as an appetite suppressant

Clobenzorex is a stimulant drug of the amphetamine chemical class used as an appetite suppressant. The drug is legally distributed in Mexico under the trade name Asenlix by Aventis.

β-Methylphenethylamine Chemical compound

β-Methylphenethylamine is an organic compound of the phenethylamine class, and a positional isomer of the drug amphetamine, with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human TAAR1 agonists. In appearance, it is a colorless or yellowish liquid.

<span class="mw-page-title-main">Etilamfetamine</span> Chemical compound

Etilamfetamine is a stimulant drug of the phenethylamine and amphetamine chemical classes. It was invented in the early 20th century and was subsequently used as an anorectic or appetite suppressant in the 1950s, but was not as commonly used as other amphetamines such as amphetamine, methamphetamine, and benzphetamine, and was largely discontinued once newer drugs such as phenmetrazine were introduced. It most likely acts primarily as a dopamine releasing agent. Its activity as a norepinephrine or serotonin releasing agent is not known.

<span class="mw-page-title-main">Mazindol</span> Stimulant drug and appetite suppressant

Mazindol is a stimulant drug which is used as an appetite suppressant. It was developed by Sandoz-Wander in the 1960s.

<span class="mw-page-title-main">Mefenorex</span> Pharmaceutical drug

Mefenorex is a stimulant drug which was used as an appetite suppressant. It is an amphetamine derivative which was developed in the 1970s and used for the treatment of obesity. Mefenorex produces amphetamine as a metabolite, and has been withdrawn in many countries despite having only mild stimulant effects and relatively little abuse potential.

<span class="mw-page-title-main">Methylhexanamine</span> Chemical compound

Methylhexanamine is an indirect sympathomimetic drug invented and developed by Eli Lilly and Company and marketed as an inhaled nasal decongestant from 1948 until it was voluntarily withdrawn from the market in the 1980s.

Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).

Oxilofrine is a substituted phenethylamine stimulant drug chemically related to ephedrine and to synephrine.

References

  1. 1 2 3 Seyffart G (1991). Drug dosage in renal insufficiency. Springer. pp. 245–246. ISBN   978-0-7923-0964-2.
  2. 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.
  3. Warembourg H, Jaillard J. Clinical experimentation with fenproporex in the treatment of obesity. Apropos of 40 cases. (French). Journal de la Faculte de médecine et de pharmacie de l'Universite de Lille. 1968 Mar;13(3):Suppl:273-6.
  4. Tognoni G, Morselli PL, Garattini S (October 1972). "Amphetamine concentrations in rat brain and human urine after fenproporex administration". European Journal of Pharmacology. 20 (1): 125–6. doi:10.1016/0014-2999(72)90227-0. PMID   4637940.
  5. Cody JD (December 1993). "Metabolic Precursors to Amphetamine and Methamphetamine". Forensic Science Review. 5 (2): 109–27. PMID   26270078.
  6. Pélissier-Alicot AL, Piercecchi-Marti MD, Bartoli C, Kuhlmann E, Coiffait PE, Sanvoisin A, et al. (March 2006). "Abusive prescription of psychostimulants: a study of two cases". Journal of Forensic Sciences. 51 (2): 407–10. doi:10.1111/j.1556-4029.2006.00078.x. PMID   16566781. S2CID   39460850.
  7. Cohen PA (March 2009). "Imported fenproporex-based diet pills from Brazil: a report of two cases". Journal of General Internal Medicine. 24 (3): 430–3. doi:10.1007/s11606-008-0878-4. PMC   2642570 . PMID   19096898.
  8. Cohen PA, McCormick D, Casey C, Dawson GF, Hacker KA (June 2009). "Imported compounded diet pill use among Brazilian women immigrants in the United States". Journal of Immigrant and Minority Health. 11 (3): 229–36. doi:10.1007/s10903-007-9099-x. PMID   18066718. S2CID   8730835.
  9. Cohen PA, Goday A, Swann JP (September 2012). "The return of rainbow diet pills". American Journal of Public Health. 102 (9): 1676–86. doi:10.2105/AJPH.2012.300655. PMC   3482033 . PMID   22813089.
  10. "Consumer Directed Questions and Answers about FDA's Initiative Against Contaminated Weight Loss Products". FDA/Center for Drug Evaluation and Research. Archived from the original on 17 March 2009.
  11. "21 CFR 1308.14(e)(4)". U.S. Government Printing Office. Archived from the original on 2011-10-16. Retrieved 2011-04-20.
  12. The 2009 Prohibited List International Standard Archived February 3, 2009, at the Wayback Machine . World Anti-Doping Agency (2009). Retrieved on 2009-08-18.