Basic information
- CAS
15686-61-0- Standard SMILES
CC(Cc1ccccc1)NCCC#N- InChIKey
IQUFSXIQAFPIMR-UHFFFAOYSA-N- Molecular formula
- C12H16N2
- Average molar mass
- 188.27 g/mol
- Monoisotopic mass
- 188.13134852
Overview
Fenproporex is a member of amphetamines.
Names & identifiers
- Preferred name
- Fenproporex
- IUPAC
- 3-(1-phenylpropan-2-ylamino)propanenitrile
- English name
- 3-[(1-methyl-2-phenylethyl)amino]propiononitrile
- Molecular formula
- C12H16N2
- Molecular weight
- 188.27
Names & synonyms
FENPROPOREXFemproporex16397-28-7FenorexW0194S5FOADTXSID0043921J268.797F3-[(1-phenylpropan-2-yl)amino]propanenitrileFenproporexum3-((1-phenylpropan-2-yl)amino)propanenitrileRefChem:140202DTXCID8023921
Show more names
FerrproporexEinecs 240-444-4Cyanoethylamphetamine3-[(2-Phenyl-1-methylethyl)amino]propanenitrile3-[(1-Methyl-2-phenylethyl)amino]propanenitrile3-[(1-methyl-2-phenylethyl)amino]propiononitrilePropanenitrile, 3-[(1-methyl-2-phenylethyl)amino]-
239-772-0240-444-43-(1-phenylpropan-2-ylamino)propanenitrileDesobesiFenproporex (INN)FENPROPOREX [INN]Fenproporex [INN:DCF]Femproporex [INN-Spanish]
Database identifiers
- CAS
15686-61-0、16397-28-7- PubChem CID
- 61810
- DTXSID
DTXSID0043921- ChEMBL
CHEMBL2105566- ChEBI
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 35.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 5
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 186
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Stimulants
DEA Schedule IV Controlled Substance -> Stimulants
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Human DrugsPharmaceuticals
Physicochemical properties
- Boiling point
- 126 · 126-127 °C(Press: 2 Torr)
- Density
- 0.986 · 0.986±0.06 g/cm3(Predicted)
- pka
- 7.9 · 7.90±0.28(Predicted)
- FDA UNII
- 194 S5FOA · W0194S5FOA
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationDEA schedule IV controlled substance
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Chemistry & industry
Pharmacology
PharmacodynamicsFenproporex 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]
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]
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]
Absorption, Distribution and Excretion
Renally eliminated in the urine, mainly as amphetamine, but 5-9% as unchanged drug.
The amphetamine metabolite can be detected for several days after the administration of forproporex (up to 119h, in one study). [2]
Uses & manufacturing
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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