ContaminantDB: Fenproporex

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-06-03 11:17:17 UTC

Update Date

2016-11-09 01:22:59 UTC

Accession Number

CHEM043803

Identification

Common Name

Fenproporex

Class

Small Molecule

Description

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. However, in clinical practice, central nervous system stimulative effects are less notorious than with some other agents such as diethylpropion and mazindol. 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, 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.

Contaminant Sources

STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Fenorex	Kegg
Fenproporex monohydrochloride	MeSH
Fenproporex monohydrochloride, (+-)-isomer	MeSH
Ifa diety	MeSH
Fenproporex, (+-)-isomer	MeSH

Chemical Formula

C₁₂H₁₆N₂

Average Molecular Mass

188.269 g/mol

Monoisotopic Mass

188.131 g/mol

CAS Registry Number

16397-28-7

IUPAC Name

3-[(1-phenylpropan-2-yl)amino]propanenitrile

Traditional Name

fenproporex

SMILES

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

InChI Identifier

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

InChI Key

IQUFSXIQAFPIMR-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Amphetamines and derivatives

Alternative Parents

Substituents

Amphetamine or derivatives
Phenylpropane
Aralkylamine
Secondary amine
Nitrile
Carbonitrile
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	2.14	ALOGPS
logP	2.01	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	7.88	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.24 m³·mol⁻¹	ChemAxon
Polarizability	22.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014m-9600000000-4638d290c61f959a86b9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1900000000-39ea645836ae34df3bad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0v4i-8900000000-fc50b0ee9f48878b7629	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udl-9200000000-2a058391d3ae665a7bbc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-5dae440ca644f76a25b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2900000000-dd0429db7b0e0780f65d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9500000000-4e2cd93f29835fd4b069	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-3900000000-d798f55f0f3645c7a53d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-ea7ddc7550ea36a99285	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-f14fb4de4c22179b8690	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3900000000-3fdf6204e62b10634055	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9700000000-a45303877a0eafe2ea1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-5cd14ec8651fea008118	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01550

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Fenproporex

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

61810

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Fenproporex (CHEM043803)

Structure for CHEM043803: Fenproporex