Tiflorex
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Tiflorex (TFX), formerly known as flutiorex, is a stimulantScript error: No such module "Unsubst". 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.
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
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
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