Fenfluramine

Title: Fenfluramine
CAS Registry Number: 458-24-2
CAS Name: N-Ethyl-a-methyl-3-(trifluoromethyl)benzeneethanamine
Additional Names: N-ethyl-a-methyl-m-(trifluoromethyl)phenethylamine; 2-ethylamino-1-(3-trifluoromethylphenyl)propane
Manufacturers' Codes: S-768
Molecular Formula: C12H16F3N
Molecular Weight: 231.26
Percent Composition: C 62.32%, H 6.97%, F 24.65%, N 6.06%
Literature References: Prepn: L. G. Beregi et al., FR M1658; eidem, US 3198833 (1963, 1965 both to Sci. Union et Cie Soc. Franc. Recherche Méd.). Prepn of optical isomers: eidem, US 3198834 (1965 to Sci. Union et Cie Soc. Franc. Recherche Med.). Pharmacology: Presse Med. 71, 181 (1963). Pharmacology and toxicity of isomers and racemate: J. C. Le Douarec et al., Arch. Int. Pharmacodyn. Ther. 161, 206 (1966). Pharmacokinetics: S. Caccia et al., Eur. J. Clin. Pharmacol. 29, 221 (1985). Clinical trial of dextrofenfluramine in refractory obesity: N. Finer et al., Curr. Ther. Res. 38, 847 (1985). Comprehensive review: Pinder et al., Drugs 10, 241-323 (1975).
Properties: bp12 108-112°. LD50 i.p. in mice: 144 mg/kg (US 3198833).
Boiling point: bp12 108-112°
Toxicity data: LD50 i.p. in mice: 144 mg/kg
Derivative Type: Hydrochloride
CAS Registry Number: 404-82-0
Trademarks: Acino (IMA); Adipomin (Streuli); Obedrex (Beta); Pesos (Valeas); Ponderal (Servier); Ponderax (Selpharm); Ponderex (Robins); Pondimin (Robins); Rotondin (Casasco)
Molecular Formula: C12H16F3N.HCl
Molecular Weight: 267.72
Percent Composition: C 53.84%, H 6.40%, F 21.29%, N 5.23%, Cl 13.24%
Properties: Crystals from ethanol + ether, mp 166°.
Melting point: mp 166°
Derivative Type: d-Form
CAS Registry Number: 3239-44-9
Additional Names: Dexfenfluramine; dextrofenfluramine
Properties: [a]D25 +9.5° (c = 8 in ethanol). LD50 orally in rats: 114.6 mg/kg (Le Douarec).
Optical Rotation: [a]D25 +9.5° (c = 8 in ethanol)
Toxicity data: LD50 orally in rats: 114.6 mg/kg (Le Douarec)
Derivative Type: d-Form hydrochloride
CAS Registry Number: 3239-45-0
Trademarks: Adifax (Servier); Glypolix (Stroder); Isomeride (Ardix); Redux (Wyeth-Ayerst)
Properties: Crystals from ethyl acetate, mp 160-161°.
Melting point: mp 160-161°
Derivative Type: l-Form
CAS Registry Number: 37577-24-5
Properties: [a]D25 -9.6° (c = 8 in ethanol). LD50 orally in rats: 195 mg/kg (Le Douarec).
Optical Rotation: [a]D25 -9.6° (c = 8 in ethanol)
Toxicity data: LD50 orally in rats: 195 mg/kg (Le Douarec)
Derivative Type: l-Form hydrochloride
CAS Registry Number: 3616-78-2
Properties: Crystals from ethyl acetate, mp 160-161°.
Melting point: mp 160-161°
NOTE: This is a controlled substance: 21 CFR, 1308.14.
Therap-Cat: Anorexic.
Keywords: Anorexic.
Fenhexamid Fenipentol Fennel Fenoldopam Fenoprofen

Fenfluramine
Fenfluramine.svg
Systematic (IUPAC) name
(RS)-N-ethyl- 1-[3-(trifluoromethyl)phenyl]propan- 2-amine
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat. B2 (AU) C (US)
Legal status Prescription Only (S4) (AU) Schedule IV (US)
Routes Oral
Pharmacokinetic data
Half-life 20 hours
Identifiers
CAS number 458-24-2 YesY
ATC code A08AA02
PubChem CID 3337
DrugBank DB00574
ChemSpider 3220 YesY
UNII 2DS058H2CF YesY
KEGG D07945 YesY
ChEBI CHEBI:5000 YesY
ChEMBL CHEMBL87493 YesY
Chemical data
Formula C12H16F3N 
Mol. mass 231.26 g/mol
 YesY (what is this?)  (verify)

Fenfluramine (3-trifluoromethyl-N-ethylamphetamine, trade names Pondimin, Ponderax and Adifax) is a drug that was part of the Fen-Phen anti-obesity medication (the other drug being phentermine). Fenfluramine was introduced on the U.S. market in 1973. It is the racemic mixture of two enantiomers, dextrofenfluramine and levofenfluramine. It increases the level of the neurotransmitter serotonin, a chemical that regulates mood, appetite and other functions. Fenfluramine causes the release of serotonin by disrupting vesicular storage of the neurotransmitter, and reversing serotonin transporter function.[1] The result is a feeling of fullness and loss of appetite.