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
Molecular 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]

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

Safety

As of 2014, no formal human studies with unifiram have been conducted.

References

  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. PMID 14600801. doi:10.1007/s00210-003-0812-6. 
  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. PMID 12070754. doi:10.1007/s00210-002-0577-3. 
  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. PMID 16834757. doi:10.1111/j.1527-3458.2006.00039.x. 
  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. PMID 14697772. doi:10.1016/j.bmc.2003.10.025. 
  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. PMID 17981042. doi:10.1016/j.bmc.2007.10.050. 
  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. PMID 18954993. doi:10.1016/j.bmc.2008.10.017. 
  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. PMID 16787332. doi:10.2174/1573406054864142. 
  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.