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Fladrafinil

From Wikipedia, the free encyclopedia
(Redirected fromCRL-40,941)
Wakefulness-promoting drug
Not to be confused withFlmodafinil.
Pharmaceutical compound
Fladrafinil
Clinical data
Other namesCRL-40,941; Fluorafinil; Bisfluoroadrafinil
Routes of
administration
By mouth
ATC code
  • None
Legal status
Legal status
Identifiers
  • 2-{[Bis(4-fluorophenyl)methyl]sulfinyl}-N-hydroxyacetamide
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC15H13F2NO3S
Molar mass325.33 g·mol−1
3D model (JSmol)
  • C1=CC(=CC=C1C(C2=CC=C(C=C2)F)S(=O)CC(=O)NO)F
  • InChI=1S/C15H13F2NO3S/c16-12-5-1-10(2-6-12)15(22(21)9-14(19)18-20)11-3-7-13(17)8-4-11/h1-8,15,20H,9H2,(H,18,19) ☒N
  • Key:VKGUUSVYPXTWMA-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Fladrafinil (developmental code nameCRL-40,941), also known asfluorafinil or asbisfluoroadrafinil, is awakefulness-promoting agent related tomodafinil that was never marketed.[1][2][3] It is sold online and used non-medically as anootropic (cognitive enhancer).[1][2][3]

Modafinil and its analogues are known to act asdopamine reuptake inhibitors and this is thought to be involved in their wakefulness-promoting effects.[1]Chemically, fladrafinil is aderivative ofadrafinil (N-hydroxymodafinil) and is also known as bisfluoroadrafinil (it is thebis(4-fluoro)phenyl ring-substituted derivative of adrafinil).[1] It is closely related toflmodafinil (CRL-40,940; bisfluoromodafinil).[1][2][3]

Pharmacology

[edit]

Fladrafinil has been found to produceantiaggressive effects in animals, whichadrafinil does not produce.[4][failed verification] Fladrafinil is purportedly 3 to 4 times morepotent than adrafinil in this action.[4]

Chemistry

[edit]
See also:List of modafinil analogues and derivatives

Analogues of fladrafinil includemodafinil,armodafinil ((R)-modafinil),esmodafinil ((S)-modafinil),adrafinil (CRL-40,028;N-hydroxymodafinil),flmodafinil (CRL-40,940; bisfluoromodafinil), andCE-123, among others.[2]

History

[edit]

Fladrafinil appears to have first beenpatented in the 1980s.[5]

Research

[edit]

Thepharmacokinetics of fladrafinil are being studied.[6]

References

[edit]
  1. ^abcdeSousa A, Dinis-Oliveira RJ (2020). "Pharmacokinetic and pharmacodynamic of the cognitive enhancer modafinil: Relevant clinical and forensic aspects".Subst Abus.41 (2):155–173.Bibcode:2020JPkR...41..155S.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
  2. ^abcdSchifano 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.hdl:2299/25614.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].
  3. ^abcDowling 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.
  4. ^abUS 4489095, Lafon L, "Halogenobenzhydrylsulfinylacetohydroxamic acids", published 1984-12-18, assigned to Laboratoire L. Lafon 
  5. ^"Fladrafinil".PubChem. Retrieved18 August 2024.
  6. ^"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. Retrieved18 August 2024.
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