Fladrafinil (developmental code name CRL-40,941), also known as fluorafinil or as bisfluoroadrafinil, is a

wakefulness-promoting agent A wakefulness-promoting agent (WPA), or wake-promoting agent, is a drug that increases wakefulness and arousal. They are similar to but distinct from psychostimulants, which not only promote wakefulness but also produce other more overt central ...

related to

modafinil Modafinil, sold under the brand name Provigil among others, is a central nervous system (CNS) stimulant and wakefulness-promoting agent, eugeroic (wakefulness promoter) medication used primarily to treat narcolepsy, a sleep disorder characteri ...

that was never marketed. It is sold online and used non-medically as a

nootropic Nootropics ( or ) (colloquially brain supplements, smart drugs, cognitive enhancers, memory enhancers, or brain boosters) are chemical substances which purportedly improve cognitive functions, such as attention, memory, wakefulness, and self ...

(cognitive enhancer). Modafinil and its analogues are known to act as

dopamine reuptake inhibitor A dopamine reuptake inhibitor (DRI) is a class of drug which acts as a reuptake inhibitor of the monoamine neurotransmitter dopamine by blocking the action of the dopamine transporter (DAT). Reuptake inhibition is achieved when extracellular dop ...

s and this is thought to be involved in their wakefulness-promoting effects.

Chemically A chemical reaction is a process that leads to the chemical transformation of one set of chemical substances to another. When chemical reactions occur, the atoms are rearranged and the reaction is accompanied by an energy change as new products ...

, fladrafinil is a

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

adrafinil Adrafinil, sold under the brand name Olmifon, is a wakefulness-promoting medication that was formerly used in France to improve alertness, attention, wakefulness, and mood, particularly in the elderly. It was also used off-label by individuals w ...

(''N''-hydroxymodafinil) and is also known as bisfluoroadrafinil (it is the ''bis''(4-

fluoro Fluorine is a chemical element; it has symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as pale yellow diatomic gas. Fluorine is extremely reactive as it reacts with all other elements except for the lig ...

)

phenyl ring In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...

substituted Substitution may refer to: Arts and media *Substitution (poetry), a variation in poetic scansion *Substitution (theatre), an acting methodology Music *Chord substitution, swapping one chord for a related one within a chord progression *Tritone ...

derivative of adrafinil). It is closely related to

flmodafinil Flmodafinil (developmental code names CRL-40,940, NLS-4, JBG01-41), also known as bisfluoromodafinil and lauflumide, is a wakefulness-promoting agent related to modafinil which has been developed for treatment of a variety of different medical ...

(CRL-40,940; bisfluoromodafinil).

Pharmacology

Fladrafinil has been found to produce

antiaggressive A serenic, or anti-aggressive drug, is a type of drug which reduces the capacity for aggression. Examples Serotonergic agents The recreational drug MDMA ("ecstasy") and a variety of related drugs have been described as ''empathogen-entactogens' ...

effects in animals, which

does not produce. Fladrafinil is purportedly 3 to 4times more potent than adrafinil in this action.

Chemistry

Analogues of fladrafinil include

armodafinil Armodafinil, sold under the brand name Nuvigil, is a wakefulness-promoting medication which is used to treat excessive daytime sleepiness associated with obstructive sleep apnea, narcolepsy, and shift work disorder. It is also used off-label ...

((''R'')-modafinil),

esmodafinil Esmodafinil (also known as (S)-modafinil or (+)-modafinil; developmental code name CRL-40983) is the enantiopure (''S'')-(+)-enantiomer of modafinil. Unlike armodafinil ((''R'')-(–)-modafinil), esmodafinil has never been marketed on its own. ...

((''S'')-modafinil),

(CRL-40,028; ''N''-hydroxymodafinil),

(CRL-40,940; bisfluoromodafinil), and

CE-123 CE-123, or as the active enantiomer (''S'')-CE-123, is an analog of modafinil, the most researched of a series of structurally related heterocyclic derivatives. In animal studies, CE-123 was found to improve performance on tests of learning and m ...

, among others.

History

Fladrafinil appears to have first been

patent A patent is a type of intellectual property that gives its owner the legal right to exclude others from making, using, or selling an invention for a limited period of time in exchange for publishing an sufficiency of disclosure, enabling discl ...

ed in the 1980s.

Research

The

pharmacokinetics Pharmacokinetics (from Ancient Greek ''pharmakon'' "drug" and ''kinetikos'' "moving, putting in motion"; see chemical kinetics), sometimes abbreviated as PK, is a branch of pharmacology dedicated to describing how the body affects a specific su ...

of fladrafinil are being studied.

References

{{Stimulants 4-Fluorophenyl compounds Abandoned drugs Designer drugs Drugs with unknown mechanisms of action Hydroxamic acids Prodrugs Stimulants Sulfoxides Wakefulness-promoting agents Modafinil analogues