List of modafinil analogues and derivatives explained

This page lists chemical compounds similar to modafinil, known as modafinil analogues and derivatives. These are structural analogues and derivatives of modafinil, a drug that affects dopamine levels in the brain in an unusual way (atypical dopamine reuptake inhibitor or DRI). Modafinil is a drug that helps keep people awake and alert (wakefulness-promoting agent or "eugeroic").[1]

Most of the listed modafinil analogues are drugs that specifically target dopamine reuptake (reabsorption of a neurotransmitter by a neurotransmitter transporter) with stronger effects (selective DRIs with improved potency) compared to modafinil. The modafinil analogues are of interest in the potential treatment of a condition involving the misuse of stimulant drugs (psychostimulant use disorder or PSUD), as drugs that help increase motivation (pro-motivational agents) to treat motivational disorders,[2] [3] and for treatment of neurodegenerative diseases such as Alzheimer's disease.[4] [5] [6] [7]

Modafinil analogues acting as DRIs include both drugs similar to modafinil that affect dopamine without causing stimulant effects (atypical modafinil-like non-psychostimulant DRIs) such as flmodafinil and JJC8-016 and drugs that affect dopamine in a way similar to cocaine (classical or typical cocaine-like DRIs) such as JJC8-088. Besides their potential medical use, modafinil analogues, including adrafinil, flmodafinil, fladrafinil, and modafiendz, are also sold online as substances that are believed to improve cognitive functions such as memory and focus (nootropics or "cognitive enhancers").

A limitation of some modafinil analogues such as JJC8-016 is blocking a specific protein (hERG) that can lead to heart problems (potent inhibition of the hERG antitarget and predicted cardiotoxicity).[8] [9] [10]

List of modafinil analogues and derivatives

In addition to the above, further modafinil analogues have also been described.[44] [45] [46] [47] [48] [49] [50] [51] [52] [53] [54] [55] [56]

Notes and References

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  8. Rahimi O, Cao J, Lam J, Childers SR, Rais R, Porrino LJ, Newman AH, Nader MA . The Effects of the Dopamine Transporter Ligands JJC8-088 and JJC8-091 on Cocaine versus Food Choice in Rhesus Monkeys . J Pharmacol Exp Ther . 384 . 3 . 372–381 . March 2023 . 36507847 . 9976790 . 10.1124/jpet.122.001363 . However, JJC8-016 failed cardiac safety tests by exhibiting relatively high affinity at hERG channels; thus, this analogue was abandoned from further development..
  9. Lee KH, Fant AD, Guo J, Guan A, Jung J, Kudaibergenova M, Miranda WE, Ku T, Cao J, Wacker S, Duff HJ, Newman AH, Noskov SY, Shi L . Toward Reducing hERG Affinities for DAT Inhibitors with a Combined Machine Learning and Molecular Modeling Approach . J Chem Inf Model . 61 . 9 . 4266–4279 . September 2021 . 34420294 . 9593962 . 10.1021/acs.jcim.1c00856 . From this validation set of DAT inhibitors, we noticed that a pair of analogues with similar chemical structures, JJC8-01646 and JJC8-08813 (Tanimoto similarity = 0.62, Figure S6), have opposite trends of affinities at DAT and hERG. JJC8-088 has ~90-fold higher affinity than JJC8-016 at DAT (Ki = 2.6 and 234.4 nM, respectively), but has ~2-fold lower affinity than JJC8-016 at hERG (IC50 = 0.13 and 0.06 μM, respectively)..
  10. Ku TC, Cao J, Won SJ, Guo J, Camacho-Hernandez GA, Okorom AV, Salomon KW, Lee KH, Loland CJ, Duff HJ, Shi L, Newman AH . Series of (([1,1'-Biphenyl]-2-yl)methyl)sulfinylalkyl Alicyclic Amines as Novel and High Affinity Atypical Dopamine Transporter Inhibitors with Reduced hERG Activity . ACS Pharmacol Transl Sci . 7 . 2 . 515–532 . February 2024 . 38357284 . 10.1021/acsptsci.3c00322 . 10863442 . January 5, 2025 .
  11. Schifano F, Catalani V, Sharif S, Napoletano F, Corkery JM, Arillotta D, Fergus S, Vento A, Guirguis A . Benefits and Harms of 'Smart Drugs' (Nootropics) in Healthy Individuals . Drugs . 82 . 6 . 633–647 . April 2022 . 35366192 . 10.1007/s40265-022-01701-7 . [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]..
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