Unifiram

Unifiram

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
PubChem	CID 9861054
ChemSpider	8036753
UNII	N4024LN29G
ChEMBL	CHEMBL140717
Chemical data
Formula	C13H15FN2O3S
Molar mass	298.333 g/mol
SMILES C2CN1C(=O)CCC1CN2S(=O)(=O)c(cc3)ccc3F
InChI InChI=1S/C13H15FN2O3S/c14-10-1-4-12(5-2-10)20(18,19)15-7-8-16-11(9-15)3-6-13(16)17/h1-2,4-5,11H,3,6-9H2 Key:SNRTZFZAFBIBJP-UHFFFAOYSA-N
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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]

Unifiram is not patented and, despite the lack of long-term toxicity studies, it is commonly sold online.^[9]

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

Safety

As of 2015, 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. 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.