Fladrafinil

Not to be confused with Flmodafinil.

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]

Fladrafinil

Clinical data
Other names	CRL-40,941; Fluorafinil; Bisfluoroadrafinil
Routes of administration	By mouth
ATC code	None
Legal status
Legal status	US: Not approved
Identifiers
IUPAC name 2-{[Bis(4-fluorophenyl)methyl]sulfinyl}-N-hydroxyacetamide
CAS Number	90212-80-9 Y
PubChem CID	13316557
ChemSpider	29785194 Y
UNII	5RT6X0M01F
CompTox Dashboard (EPA)	DTXSID40536590
Chemical and physical data
Formula	C15H13F2NO3S
Molar mass	325.33 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC(=CC=C1C(C2=CC=C(C=C2)F)S(=O)CC(=O)NO)F
InChI 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
NY (what is this?)  (verify)

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

Fladrafinil 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

See also: List of modafinil analogues and derivatives

Analogues 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

Fladrafinil appears to have first been patented in the 1980s.^[5]

Research

The pharmacokinetics of fladrafinil are being studied.^[6]