Fladrafinil (developmental code name CRL-40,941), also known as fluorafinil or as bisfluoroadrafinil, is a wakefulness-promoting agent related to modafinil that was never marketed.[1][2][3] It is sold online and used non-medically as a nootropic (cognitive enhancer).[1][2][3]
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| Other names | CRL-40,941; Fluorafinil; Bisfluoroadrafinil |
| Routes of administration | By mouth |
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| Formula | C15H13F2NO3S |
| Molar mass | 325.33 g·mol−1 |
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Modafinil and its analogues are known to act as dopamine reuptake inhibitors and this is thought to be involved in their wakefulness-promoting effects.[1] Chemically, fladrafinil is a derivative of adrafinil (N-hydroxymodafinil) and is also known as bisfluoroadrafinil (it is the bis(4-fluoro) phenyl ring-substituted derivative of adrafinil).[1] It is closely related to flmodafinil (CRL-40,940; bisfluoromodafinil).[1][2][3]
Pharmacology
editFladrafinil has been found to produce antiaggressive effects in animals, which adrafinil does not produce.[4][failed verification] Fladrafinil is purportedly 3 to 4 times more potent than adrafinil in this action.[4]
Chemistry
editAnalogues of fladrafinil include modafinil, armodafinil ((R)-modafinil), esmodafinil ((S)-modafinil), adrafinil (CRL-40,028; N-hydroxymodafinil), flmodafinil (CRL-40,940; bisfluoromodafinil), and CE-123, among others.[2]
History
editFladrafinil appears to have first been patented in the 1980s.[5]
Research
editThe pharmacokinetics of fladrafinil are being studied.[6]
References
edit- ^ a b c d e Sousa A, Dinis-Oliveira RJ (2020). "Pharmacokinetic and pharmacodynamic of the cognitive enhancer modafinil: Relevant clinical and forensic aspects". Subst Abus. 41 (2): 155–173. doi:10.1080/08897077.2019.1700584. PMID 31951804.
Modafinil is a highly researched compound, with many analogues created and studied (Figure 1); the wakefulness promoting agents CRL-40,490 and modafiendz are the fluoro and N-methyl analogs of modafinil and the CRL-40,491 is the fluoro analog of adrafinil.30,31 [...] Although the long-term effects in healthy individuals are unknown, modafinil is easily available online with limited information about the use of and potential harms related to the drug.20,209 Other possibilities available from online shops and other retail outlets include adrafinil, CRL-40,940, CRL40,941 and modafiendz.30 Alternatively to online purchase, students also report to obtain stimulants from a pharmacy with or without prescription, from colleagues, friends or family, or from an herbalist.20
- ^ a b c d Schifano F, Catalani V, Sharif S, Napoletano F, Corkery JM, Arillotta D, Fergus S, Vento A, Guirguis A (April 2022). "Benefits and Harms of 'Smart Drugs' (Nootropics) in Healthy Individuals". Drugs. 82 (6): 633–647. doi:10.1007/s40265-022-01701-7. PMID 35366192.
[Modafinil] is widely available for online purchase [105] and it is of interest that a range of modafinil derivatives are actively being discussed on web fora, including: adrafinil, fladrafinil, flmodafinil, and N-methyl-4,4′-difluoro-modafinil [8]. Finally, the modafinil R-enantiomer armodafinil, which is being used to improve wakefulness in patients with excessive sleepiness [106], is currently the subject of an anecdotal debate relating to its properties as a [cognitive enhancer] [107].
- ^ a b c Dowling G, Kavanagh PV, Talbot B, O'Brien J, Hessman G, McLaughlin G, Twamley B, Brandt SD (March 2017). "Outsmarted by nootropics? An investigation into the thermal degradation of modafinil, modafinic acid, adrafinil, CRL-40,940 and CRL-40,941 in the GC injector: formation of 1,1,2,2-tetraphenylethane and its tetra fluoro analog" (PDF). Drug Test Anal. 9 (3): 518–528. doi:10.1002/dta.2142. PMID 27928893.
- ^ a b US 4489095, Lafon L, "Halogenobenzhydrylsulfinylacetohydroxamic acids", published 1984-12-18, assigned to Laboratoire L. Lafon
- ^ "Fladrafinil". PubChem. Retrieved 18 August 2024.
- ^ "Investigations into the metabolism and elimination of flmodafinil and fladrafinil as well as their prevalence in elite sports". World Anti Doping Agency. 23 May 2024. Retrieved 18 August 2024.