3973. Fenfluramine

Nomenclature

CAS number: 458-24-2
N-Ethyl-α-methyl-3-(trifluoromethyl)benzeneethanamine; N-ethyl-α-methyl-m-(trifluoromethyl)phenethylamine; 2-ethylamino-1-(3-trifluoromethylphenyl)propane; S-768.
C12H16F3N; mol wt 231.26.
C 62.32%, H 6.97%, F 24.65%, N 6.06%.

Description and 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).

Chemical structure

Properties

bp12 108-112°. LD50 i.p. in mice: 144 mg/kg (US 3198833).

Derivative

Hydrochloride.

Nomenclature

CAS number: 404-82-0
Acino (IMA); Adipomin (Streuli); Obedrex (Beta); Pesos (Valeas); Ponderal (Servier); Ponderax (Selpharm); Ponderex (Robins); Pondimin (Robins); Rotondin (Casasco).
C12H16F3N.HCl; mol wt 267.72.
C 53.84%, H 6.40%, F 21.29%, N 5.23%, Cl 13.24%.

Properties

Crystals from ethanol + ether, mp 166°.

Derivative

d-Form.

Nomenclature

CAS number: 3239-44-9
Dexfenfluramine; dextrofenfluramine.

Properties

[α]D25 +9.5° (c = 8 in ethanol). LD50 orally in rats: 114.6 mg/kg (Le Douarec).

Derivative

d-Form hydrochloride.

Nomenclature

CAS number: 3239-45-0
Adifax (Servier); Glypolix (Stroder); Isomeride (Ardix); Redux (Wyeth-Ayerst).

Properties

Crystals from ethyl acetate, mp 160-161°.

Derivative

l-Form.

Nomenclature

CAS number: 37577-24-5

Properties

[α]D25 -9.6° (c = 8 in ethanol). LD50 orally in rats: 195 mg/kg (Le Douarec).

Derivative

l-Form hydrochloride.

Nomenclature

CAS number: 3616-78-2

Properties

Crystals from ethyl acetate, mp 160-161°.

Note

This is a controlled substance: 21 CFR, 1308.14.

Therapeutic Category

Anorexic.

Keywords

Anorexic