ContaminantDB: Dexfenfluramine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:35 UTC

Update Date

2026-04-06 09:02:54 UTC

Accession Number

CHEM002371

Identification

Common Name

Dexfenfluramine

Class

Small Molecule

Description

Dexfenfluramine, also marketed under the name Redux, is a serotoninergic anorectic drug. It was for some years in the mid-1990s approved by the United States Food and Drug Administration for the purposes of weight loss. However, following multiple concerns about the cardiovascular side-effects of the drug, such approval was withdrawn.

Contaminant Sources

HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amine
Anti-Obesity Agent
Appetite Depressant
Drug
Food Toxin
Metabolite
Organic Compound
Organofluoride
Serotonin Agonist
Serotonin Receptor Agonist
Serotonin Reuptake Inhibitor
Serotonin Uptake Inhibitor
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Fenfluramine	ChEBI
(S)-N-Ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine	ChEBI
D-N-Ethyl-alpha-methyl-m-trifluoromethylphenethylamine	ChEBI
Dexfenfluramina	ChEBI
Dexfenfluraminum	ChEBI
Dextrofenfluramine	ChEBI
D-N-Ethyl-a-methyl-m-trifluoromethylphenethylamine	Generator
D-N-Ethyl-α-methyl-m-trifluoromethylphenethylamine	Generator
(S)-Fenfluramine	HMDB
Dexfenfluramine hydrochloride	HMDB
Redux	HMDB
Wyeth brand OF dexfenfluramine hydrochloride	HMDB
Hydrochloride, dexfenfluramine	HMDB
Dexfenfluramine	ChEBI

Chemical Formula

C₁₂H₁₆F₃N

Average Molecular Mass

231.257 g/mol

Monoisotopic Mass

231.123 g/mol

CAS Registry Number

3239-44-9

IUPAC Name

ethyl[(2S)-1-[3-(trifluoromethyl)phenyl]propan-2-yl]amine

Traditional Name

dexfenfluramine

SMILES

CCN[C@@H](C)CC1=CC=CC(=C1)C(F)(F)F

InChI Identifier

InChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3/t9-/m0/s1

InChI Key

DBGIVFWFUFKIQN-VIFPVBQESA-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
Trifluoromethylbenzene
Phenylpropane
Aralkylamine
Secondary aliphatic amine
Secondary amine
Alkyl fluoride
Hydrocarbon derivative
Organonitrogen compound
Organofluoride
Organohalogen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Alkyl halide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

fenfluramine (CHEBI:439329 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	2.15e-02 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	3.3	ALOGPS
logP	3.47	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	10.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	59.2 m³·mol⁻¹	ChemAxon
Polarizability	22.69 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	splash10-00di-9110000000-1bb444f1022b28d94dc0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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	splash10-001i-1190000000-7fbe4443e51aea6826c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001r-8890000000-5cd73b17e1103d99e7fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ov-9610000000-58d820854fe8992bc6a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-96055c6c721aecfc76f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2190000000-2f8c88fb4bc53943412f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9410000000-a342d0ae14c5230c00a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0290000000-ac3db862ce9c06ed67f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0910000000-6cb4ba049f7be32b0f1c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1900000000-43131e1ffc852067efa9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-8ae4a9b01f14913328e8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a5i-0930000000-c301feb5a0d5278285b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0900000000-30767724225603e597e1	Spectrum

Toxicity Profile

Route of Exposure

Well-absorbed from the gastrointestinal tract.

Mechanism of Toxicity

Dexfenfluramine binds to the serotonin reuptake pump. This causes inhbition of serotonin reuptake. The increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding behavior located in the hypothalamus. This suppresses the appetite for carbohydrates.

Metabolism

Half Life: 17-20 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

A serotoninergic anorectic drug once used for the purposes of weight loss, but pulled out from the global market following multiple concerns about the cardiovascular side-effects of the drug. [Wikipedia]

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include respiratory failure and cardiac arrest leading to death.

Treatment

General supportive measures for oral drug overdose should be instituted. Measures that have been used in dexfenfluramine overdose cases include aspiration of gastric contents, gastric lavage with activated charcoal, osmotic diuresis, forced acid diuresis, and careful monitoring of CNS or respiratory depression. The effectiveness of dialysis is not known. Patients should be followed closely until there is no further evidence of drug-related CNS effects. No specific therapy for dexfenfluramine overdose is known. (3)

Concentrations

Not Available

External Links

DrugBank ID

DB01191

HMDB ID

HMDB0015322

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID