Tiflorex

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Tiflorex
Tiflorex standardized.png
Clinical data
ATC code
  • none
Identifiers
  • (RS)-N-ethyl-1-{3-[(trifluoromethyl)thio]phenyl}propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H16F3NS
Molar mass 263.32 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • CCNC(C)Cc1cccc(c1)SC(F)(F)F
  • InChI=1S/C12H16F3NS/c1-3-16-9(2)7-10-5-4-6-11(8-10)17-12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3 X mark.svgN
  • Key:HNONSDNCRNUTCT-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Tiflorex (TFX), formerly known as flutiorex, is a stimulant [ citation needed ] amphetamine that was under development as an appetite suppressant in the 1970s, [1] [2] but appears to have been abandoned. It is structurally related to fenfluramine and 4-MTA.

Contents

Tiflorex went to phase II clinical trials. The extended release formulation "TFX-SR" produced significant suppression of appetite. It also caused slightly more sleep disturbances and headaches than placebo, as well as mydriasis and a self-reported decrease in arousal. It had little effect on heart rate. [2]

Tifluorex is claimed to be a more potent anorectic than fenfluramine, with twice its potency in humans [2] and 4 times its potency in rats. [3]

Pharmacology

Pharmacodynamics

The mechanism of action of tiflorex has apparently never been studied. Similar compounds such as fenfluramine, norfenfluramine and 4-MTA act as selective serotonin releasing agents and 5-HT2 receptor agonists. Fenfluramine in particular causes very similar side effects and appetite suppression at therapeutically relevant doses.

Pharmacokinetics

In rats, tiflorex is rapidly N-dealkylated to norflutiorex. Both tiflorex and norflutiorex appear to be excreted in urine. [1]

Synthesis

Patent: Tiflorex synthesis.svg
Patent:

The Rosenmund reduction of 3-(trifluoromethylthio)benzoyl chloride [51748-28-8] (1) gave 3-((trifluoromethyl)thio)benzaldehyde [51748-27-7] (2). Henry reaction with nitroethane led to 1-(2-nitroprop-1-en-1-yl)-3-[(trifluoromethyl)sulfanyl]benzene [176242-84-5] (3). With the aid of iron catalyst in concentrated HCl acid there occurred FGI into 1-(3'-trifluoromethylthiophenyl)-2-propanone, CID:21325269 (4'). Reductive amination with ethylamine and formic acid as the reductant completed the synthesis of tiflorex (5).

References

  1. 1 2 Giudicelli JF, Richer C, Berdeaux A (February 1976). "Preliminary assessment of flutiorex, a new anorectic drug, in man". British Journal of Clinical Pharmacology. 3 (1): 113–21. doi:10.1111/j.1365-2125.1976.tb00578.x. PMC   1428817 . PMID   788737.
  2. 1 2 3 Silverstone T, Fincham J, Plumley J (April 1979). "An evaluation of the anorectic activity in man of a sustained release formulation of tiflorex". British Journal of Clinical Pharmacology. 7 (4): 353–6. doi:10.1111/j.1365-2125.1979.tb00945.x. PMC   1429648 . PMID   444355.
  3. ↑ Stuart S (2013-09-11). Abstracts: Sixth International Congress of Pharmacology. Elsevier. ISBN   9781483152530.
  4. ↑ Don P. R. L. Giudicelli & Henry Najer, U.S. patent 4,148,923 (1979 to Synthelabo SA).
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