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Fenproporex

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Also known as: Desobesi, 16397-28-7, Femproporex, Fenorex, 3-(1-phenylpropan-2-ylamino)propanenitrile, 3-[(1-methyl-2-phenylethyl)amino]propiononitrile

Molecular Formula

C₁₂H₁₆N₂

Molecular Weight

188.27 g/mol

InChI Key

IQUFSXIQAFPIMR-UHFFFAOYSA-N

FDA UNII

W0194S5FOA

Fenproporex is an orally active stimulant drug, which was developed in the 1960s. It is used as an appetite suppressant and a treatment for obesity. It is listed as an illicit substance in many countries due to addiction issues and listed as a prohibited substance by the World Anti-Doping Agency. Structurally, fenproporex (N-2-cyanoethylamphetamine) falls within the phenylethamine and amphetamine chemical class of drugs. The N-2-cyanoethyl substituent was once believed to be resistant to cleavage, because fenproporex -- once recommended as an obesity treatment for patients with cardiovascular disease -- was originally claimed to lack stimulant properties. Contrary to the claim, research has demonstrated easy in vivo cleavage of the N-2-cyanothyl substituent to yield amphetamine as a metabolite. [5] However, in clinical practice, central nervous system stimulative effects are less notorious than with some other agents such as diethylpropion and mazindol. [7] In the United States fenproporex was never approved by the FDA for clinical use due to a lack of efficacy and safety data, and is listed as a drug in Schedule IV of the Controlled Substances Act. In 2006 and 2009, the FDA issued warnings that it had been detected in diet pills sold online, and imported from foreign manufacturers. Despite being banned in the United States, fenproporex has been described as the second most commonly consumed appetite suppressant worldwide, [6] with fenproporex containing anorectics still being commonly prescribed in South America. Little is known about the specific hazards of amphetamine based diet pills, however case reports have noted side effects such as chest pain, palpitations, headaches, and insomnia. In addition, placebo controlled studies have shown that participants using fenproporex experience more joint pain, sweating, blurred vision and tremor. [2]

1 2D Structure

Fenproporex

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(1-phenylpropan-2-ylamino)propanenitrile

2.1.2 InChI

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

2.1.3 InChI Key

IQUFSXIQAFPIMR-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(CC1=CC=CC=C1)NCCC#N

2.2 Other Identifiers

2.2.1 UNII

W0194S5FOA

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Fenproporex Monohydrochloride

2. Fenproporex Monohydrochloride, (+-)-isomer

3. Fenproporex, (+-)-isomer

4. Ifa Diety

2.3.2 Depositor-Supplied Synonyms

1. Desobesi

2. 16397-28-7

3. Femproporex

4. Fenorex

5. 3-(1-phenylpropan-2-ylamino)propanenitrile

6. 3-[(1-methyl-2-phenylethyl)amino]propiononitrile

7. W0194s5foa

8. Fenproporex (inn)

9. J268.797f

10. Fenproporex [inn]

11. Fenproporex [inn:dcf]

12. Femproporex [inn-spanish]

13. Fenproporexum [inn-latin]

14. 3-((1-methyl-2-phenylethyl)amino)propiononitrile

15. Einecs 239-772-0

16. Unii-w0194s5foa

17. Dea No. 1575

18. Einecs 240-444-4

19. Fenorex (tn)

20. Fenproporex [mi]

21. N-2-cyanoethylamphetamine

22. N-(2-cyanoethyl)amphetamine

23. Fenproporex [who-dd]

24. 15686-61-0

25. Schembl157687

26. Chembl2105566

27. Dtxsid0043921

28. Chebi:134837

29. (.+/-.)-n-2-cyanoethylamphetamine

30. Db01550

31. D07947

32. 3-[(1-methyl-2-phenylethyl)amino]propanenitrile #

33. Q5443577

34. (.+/-.)-3-[(.alpha.-methylphenethyl)amino]propionitrile

35. (+/-)-3-((.alpha.-methylphenethyl)amino)propionitrile

36. Propanenitrile, 3-[(1-methyl-2-phenylethyl)amino]-, (.+/-.)-

37. Propionitrile, 3-((.alpha.-methylphenethyl)amino)-, (.+/-.)-

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₆N₂
Molecular Weight	188.27 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	5
Exact Mass	188.131348519 g/mol
Monoisotopic Mass	188.131348519 g/mol
Topological Polar Surface Area	35.8 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	186
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Fenproporex is used as an appetite suppressant, and anti-obesity agent [2]; however, due to substance abuse potential, it is an illicit substance in many countries. In some countries, such as Brazil, it is still prescribed -- often in the form of diet pills (ie. Brazilian Diet Pills) which combine amphetamines, benzodiazepines, antidepressants, diuretics and laxatives. In the United States the sale of such diet pills has been banned due to concerns over side effects, and the risk of potentially fatal overdose. However, internet sales and illicit markets has lead to international availability. It has been found by primary care physicians that Brazilian immigrant women utilized imported diet pills at particularly high rates, and sometimes suffered from side effects requiring hospitalization or experienced a loss of employment. [3]

5 Pharmacology and Biochemistry

5.1 Pharmacology

Fenproporex was first claimed to not exert a stimulant effect on the body, however research into its metabolism has shown that it is converted into a considerable amount of amphetamine in the body, which leads to stimulant effects. [9]

5.2 Absorption, Distribution and Excretion

Route of Elimination

Renally eliminated in the urine, mainly as amphetamine, but 5-9% as unchanged drug.

Clearance

The amphetamine metabolite can be detected for several days after the administration of forproporex (up to 119h, in one study). [2]

5.3 Metabolism/Metabolites

A large portion, 60-80%, of fenproporex is rapidly converted into amphetamine. Besides amphetamine, and unchanged fenproporex, 14 other metabolites were identified from urine samples. Two interacting metabolic pathways are believed to exist. The major pathway is believed to involve ring-degradation by aromatic hydroxylation, methylation, and side chain degradation by N-dealkyation to form amphetamine. The minor pathway involves the beta-hydroxylation of amphetamine to form norephedrine. [6]

5.4 Mechanism of Action

Fenproporex is an amphetamine based anorectic which is rapidly metabolized into amphetamine in the body. Both acute and chronic fenproporex administration has been shown to increase brain energy metabolism in young rats, by increasing the activity of citrate synthase, malate dehydrogenase, succinate dehydrogenase, creatine kinase and complexes I,II, III, and IV. [8] Amphetamine based drugs are also known to reduce food intake. They are addictive substances due to their ability to increase dopamine release, however their anorectic effects are believed to be a result of noradrenergic neurotransmission. Activation of the alpha 1 and beta 2 adrenoceptors has been shown to decrease food intake, and drugs which release norepinephrine or block norepinephrine reuptake can activate these receptors. [3] The alpha 1 and beta 2 adrenoceptors are noted to be clinically important receptors in weight regulation. [3]