Tiflorex, formerly known as flutiorex, is a

stimulant Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...

amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...

. Its most pronounced effect is in suppression of appetite; it has little effect on pulse rate, sleep, or mood. It was found to be twice as potent an anorectic as

fenfluramine Fenfluramine, sold under the brand name Fintepla, is a serotonergic medication used for the treatment of seizures associated with Dravet syndrome and Lennox–Gastaut syndrome.https://www.accessdata.fda.gov/drugsatfda_docs/label/2022/212102s003lb ...

. SL 72.340-d was cited to be 4x the anorectant potency of fenfluramine (ED50=1.4 mg/kg vs 5.6 mg/kg).

Synthesis

The

Rosenmund reduction The Rosenmund reduction is a hydrogenation process in which an acyl chloride is selectively reduced to an aldehyde. The reaction was named after Karl Wilhelm Rosenmund, who first reported it in 1918. The reaction, a hydrogenolysis, is catalyse ...

of 3-(trifluoromethylthio)benzoyl chloride 1748-28-8(1) gave 3-((trifluoromethyl)thio)benzaldehyde 1748-27-7(2). Henry reaction with nitroethane led to 1-(2-nitroprop-1-en-1-yl)-3- trifluoromethyl)sulfanylenzene 76242-84-5(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 Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleo ...

and

formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Es ...

as the reductant completed the synthesis of tiflorex (5).

References

Anorectics Trifluoromethyl compounds Substituted amphetamines Thioethers {{nervous-system-drug-stub