Modafiendz

Modafiendz, also known as N-methyl-4,4-difluoromodafinil or as N-methylbisfluoromodafinil, 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]

Other namesN-Methyl-4,4-difluoromodafinil; Methyldifluoromodafinil; N-Methylbisfluoromodafinil; Bisfluoro-N-methylmodafinil; Methylflmodafinil

CAS Number

1613222-54-0

PubChem CID

132989661

ChemSpider

58951582

Quick facts Clinical data, Other names ...

Modafiendz
Clinical data

Other names	N-Methyl-4,4-difluoromodafinil; Methyldifluoromodafinil; N-Methylbisfluoromodafinil; Bisfluoro-N-methylmodafinil; Methylflmodafinil
Identifiers
IUPAC name 2-[bis(4-fluorophenyl)methylsulfinyl]-N-methylacetamide
CAS Number	1613222-54-0
PubChem CID	132989661
ChemSpider	58951582
UNII	223VWC34TA
CompTox Dashboard (EPA)	DTXSID501342547
Chemical and physical data
Formula	C₁₆H₁₅F₂NO₂S
Molar mass	323.36 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CNC(=O)CS(=O)C(C1=CC=C(C=C1)F)C2=CC=C(C=C2)F
InChI InChI=1S/C16H15F2NO2S/c1-19-15(20)10-22(21)16(11-2-6-13(17)7-3-11)12-4-8-14(18)9-5-12/h2-9,16H,10H2,1H3,(H,19,20) Key:MQZWTCIUDSDFCQ-UHFFFAOYSA-N

Modafiendz is the bis-fluoro and N-methylated derivative of modafinil as well as the N-methyl analogue of flmodafinil (CRL-40,940; bisfluoromodafinil) and fladrafinil (CRL-40,941; bisfluoroadrafinil).^[1]^[2]

Modafinil and its analogues have been found to act as selective dopamine reuptake inhibitors and this is thought to be involved in their wakefulness-promoting effects.^[2]

References

[1]
Napoletano F, Schifano F, Corkery JM, Guirguis A, Arillotta D, Zangani C, et al. (2020). "The Psychonauts' World of Cognitive Enhancers". Frontiers in Psychiatry. 11 546796. doi:10.3389/fpsyt.2020.546796. PMC 7516264. PMID 33024436. 2-{[bis(4-fluorophenyl)methyl]sulfinyl}-N-methylacetamide is the bis-fluoro-N-methyl analogue of the substance modafinil and is currently marketed by online sellers as a nootropic substance called 'modafiendz'.
[2]
Sousa A, Dinis-Oliveira RJ (2020). "Pharmacokinetic and pharmacodynamic of the cognitive enhancer modafinil: Relevant clinical and forensic aspects". Substance Abuse. 41 (2): 155–173. Bibcode:2020JPkR...41..155S. doi:10.1080/08897077.2019.1700584. PMID 31951804. Figure 1 presents chemical structures of modafinil and analogues. [...] 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
[3]
Dowling G, Kavanagh PV, Talbot B, O'Brien J, Hessman G, McLaughlin G, et al. (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 Testing and Analysis. 9 (3): 518–528. doi:10.1002/dta.2142. PMID 27928893. 2-[(Diphenylmethyl)sulfinyl]acetamide (modafinil) is commonly prescribed for the treatment of narcolepsy and increasing popularity and off-label use as a cognitive enhancer resulted in a reputation as an intelligence boosting 'wonder drug'. Common alternatives available from online shops and other retail outlets include 2-[(diphenylmethyl)sulfinyl]-N-hydroxyacetamide (adrafinil), 2-([bis(4-fluorophenyl)methyl]sulfinyl)acetamide (CRL-40,940), 2-([bis(4-fluorophenyl)methyl]sulfinyl)-N-hydroxyacetamide (CRL-40,941) and N-methyl-4,4-difluoro-modafinil (modafiendz), respectively. [...] CRL-40,941 and modafiendz are also wakefulness promoting agents and related to modafinil and adrafinil (Figure 1).

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References

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