Unifiram

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Unifiram
Unifiram.svg
Systematic (IUPAC) name
2-[(4-Fluorophenyl)sulfonyl]hexahydropyrrolo[1,2-a]pyrazin-6(2H)-one
Clinical data
Legal status
  • Unscheduled
Identifiers
CAS Number 272786-64-8 YesY
PubChem CID 9861054
ChemSpider 8036753 N
ChEMBL CHEMBL140717 N
Chemical data
Formula C13H15FN2O3S
Molar mass 298.333 g/mol
 NYesY (what is this?)  (verify)

Unifiram (DM-232) is an ampakine-like drug derived from biarylpropylsulfonamide,[1] and has antiamnesic and other effects in animal studies with up to a thousand times higher potency than piracetam.[2][3] A number of related compounds are known, including sunifiram (DM-235).[4][5][6] Unifiram has two enantiomers, with (R)-(+)-unifiram (dextrounifiram) being the more active isomer.[7] Unifiram is shown to reduce the duration of hypnosis induced by pentobarbital, without impairing motor coordination.[8]

Despite an absence of long-term toxicity studies, unifiram is commonly sold online.[9]

(R)-(+)-unifiram (dextrounifiram).
(R)-(+)-unifiram (dextrounifiram).

Safety[edit]

As of 2015, no formal human studies with unifiram have been conducted.

References[edit]

  1. ^ Galeotti, N.; Ghelardini, C.; Pittaluga, A.; Pugliese, A.; Bartolini, A.; Manetti, D.; Romanelli, M.; Gualtieri, F. (2003). "AMPA-receptor activation is involved in the antiamnesic effect of DM 232 (unifiram) and DM 235 (sunifiram)". Naunyn-Schmiedeberg's archives of pharmacology 368 (6): 538–545. doi:10.1007/s00210-003-0812-6. PMID 14600801. 
  2. ^ Ghelardini, C.; Galeotti, N.; Gualtieri, F.; Romanelli, M.; Bucherelli, C.; Baldi, E.; Bartolini, A. (2002). "DM235 (sunifiram): a novel nootropic with potential as a cognitive enhancer". Naunyn-Schmiedeberg's archives of pharmacology 365 (6): 419–426. doi:10.1007/s00210-002-0577-3. PMID 12070754. 
  3. ^ Romanelli, M.; Galeotti, N.; Ghelardini, C.; Manetti, D.; Martini, E.; Gualtieri, F. (2006). "Pharmacological characterization of DM232 (unifiram) and DM235 (sunifiram), new potent cognition enhancers". CNS Drug Reviews 12 (1): 39–52. doi:10.1111/j.1527-3458.2006.00039.x. PMID 16834757. 
  4. ^ Scapecchi, S.; Martini, E.; Manetti, D.; Ghelardini, C.; Martelli, C.; Dei, S.; Galeotti, N.; Guandalini, L.; Novella Romanelli, M.; Teodori, E. (2004). "Structure-activity relationship studies on unifiram (DM232) and sunifiram (DM235), two novel and potent cognition enhancing drugs". Bioorganic & Medicinal Chemistry 12 (1): 71–85. doi:10.1016/j.bmc.2003.10.025. PMID 14697772. 
  5. ^ Martini, E.; Ghelardini, C.; Dei, S.; Guandalini, L.; Manetti, D.; Melchiorre, M.; Norcini, M.; Scapecchi, S.; Teodori, E.; Romanelli, M. N. (2008). "Design, synthesis and preliminary pharmacological evaluation of new piperidine and piperazine derivatives as cognition-enhancers". Bioorganic & Medicinal Chemistry 16 (3): 1431–1443. doi:10.1016/j.bmc.2007.10.050. PMID 17981042. 
  6. ^ Martini, E.; Norcini, M.; Ghelardini, C.; Manetti, D.; Dei, S.; Guandalini, L.; Melchiorre, M.; Pagella, S.; Scapecchi, S.; Teodoria, E. (2008). "Design, synthesis and preliminary pharmacological evaluation of new analogues of DM232 (unifiram) and DM235 (sunifiram) as cognition modulators". Bioorganic & Medicinal Chemistry 16 (23): 10034–10042. doi:10.1016/j.bmc.2008.10.017. PMID 18954993. 
  7. ^ Martini, E.; Ghelardini, C.; Bertucci, C.; Dei, S.; Gualtieri, F.; Guandalini, L.; Manetti, D.; Scapecchi, S.; Teodori, E.; Romanelli, M. N. (2005). "Enantioselective synthesis and preliminary pharmacological evaluation of the enantiomers of unifiram (DM232), a potent cognition-enhancing agent". Medicinal chemistry 1 (5): 473–480. doi:10.2174/1573406054864142. PMID 16787332. 
  8. ^ Ghelardini, C.; Galeotti, N.; Gualtieri, F.; Manetti, D.; Bucherelli, C.; Baldi, E.; Bartolini, A. (2002). "The novel nootropic compound DM232 (UNIFIRAM) ameliorates memory impairment in mice and rats". Drug Development Research 56: 23. doi:10.1002/ddr.10055. 
  9. ^ Gualtieri F (2016). "Unifi nootropics from the lab to the web: a story of academic (and industrial) shortcomings". Journal of Enzyme Inhibition and Medicinal Chemistry 31 (2): 187–94. doi:10.3109/14756366.2015.1021252. PMID 25831025. Retrieved 2016-02-07. Some 12 years after their disclosure (2000) I casually found that on the web, there were dozens of sites offering Unifiram and Sunifiram as drugs that improve cognition in healthy individuals even if only few preclinical studies were done and their long-term toxicity was unknown.