ContaminantDB: Fenfluramine

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

Record Information

Version

1.0

Creation Date

2016-05-22 03:41:07 UTC

Update Date

2016-11-09 01:15:27 UTC

Accession Number

CHEM016709

Identification

Common Name

Fenfluramine

Class

Small Molecule

Description

A secondary amino compound that is 1-phenyl-propan-2-amine in which one of the meta-hydrogens is substituted by trifluoromethyl, and one of the hydrogens attached to the nitrogen is substituted by an ethyl group. It binds to the serotonin reuptake pump, causing inhbition of serotonin uptake and release of serotonin. The resulting 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. Fenfluramine was used as the hydrochloride for treatment of diabetes and obesity. It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-Fenfluramine	ChEBI
1-(m-Trifluoromethyl-phenyl)-2-ethylaminopropane	ChEBI
2-Ethylamino-1-(3-trifluoromethylphenyl)propane	ChEBI
3-(Trifluoromethyl)-N-ethyl-alpha-methylphenethylamine	ChEBI
Ethyl-[1-methyl-2-(3-trifluoromethyl-phenyl)-ethyl]-amine	ChEBI
Fenfluraminum	ChEBI
N-Ethyl-1-(3-(trifluoromethyl)phenyl)propan-2-amine	ChEBI
N-Ethyl-alpha-methyl-3-trifluoromethylphenethylamine	ChEBI
Ponderax	Kegg
3-(Trifluoromethyl)-N-ethyl-a-methylphenethylamine	Generator
3-(Trifluoromethyl)-N-ethyl-α-methylphenethylamine	Generator
N-Ethyl-a-methyl-3-trifluoromethylphenethylamine	Generator
N-Ethyl-α-methyl-3-trifluoromethylphenethylamine	Generator
Isomeride	MeSH
Fenfluramine hydrochloride, (+-)-isomer	MeSH
Fenfluramine, (+-)-isomer	MeSH
Fenfluramine, R-isomer	MeSH
Pondimin	MeSH
Robins brand OF fenfluramine hydrochloride	MeSH
Fenfluramine hydrochloride, R isomer	MeSH
Fenfluramine, R isomer	MeSH
Fenfluramine hydrochloride	MeSH
Fenfluramine hydrochloride, R-isomer	MeSH
Hydrochloride, fenfluramine	MeSH

Chemical Formula

C₁₂H₁₆F₃N

Average Molecular Mass

231.257 g/mol

Monoisotopic Mass

231.123 g/mol

CAS Registry Number

458-24-2

IUPAC Name

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

Traditional Name

redux

SMILES

CCNC(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

InChI Key

DBGIVFWFUFKIQN-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
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

secondary amino compound (CHEBI:5000 )
(trifluoromethyl)benzenes (CHEBI:5000 )

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	0.022 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	22.51 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-9210000000-aba8427e1b8b103e780b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0090000000-41a095f72665e3a6fc34	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0910000000-481b943f32db11f34ee9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-b47283685814bef28517	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-68de81754e901e800d97	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-051ff0ad0ba0c9f76270	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0290000000-a4eef1b513aee06fe04c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00kb-2930000000-e89db6ca285f5e38a85e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4j-5900000000-d43b57acff766553a26a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9600000000-b49ac50c8a44403f71f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0aor-9400000000-98167d6254e10b1cb5fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0a4r-0900000000-8fa48db488adb62ea334	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-053r-0970000000-f9a49d7622ec3ba9a1d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4i-0900000000-ab20d5fae96b357efb96	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4i-0900000000-486062095dc4b5f9673d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4i-0900000000-f339087f5b3e001e72e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4i-0900000000-7d7a0ce1b53c5f8aca3e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-fca90351c2c40bcbea2d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0910000000-0fab7ed0d9d454eb1b62	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-2e91ebdd7e7834225fc9	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

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

DB00574

HMDB ID

HMDB0252200

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

Fenfluramine

Chemspider ID

3220

ChEBI ID

5000

PubChem Compound ID

Not Available

Kegg Compound ID

C06996

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11716826

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15637164

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15677429

Fenfluramine (CHEM016709)

Structure for CHEM016709: Fenfluramine