Unifiram

Unifiram
Legal status
Legal status	In general: unscheduled;
Identifiers
	IUPAC name 2-[(4-Fluorophenyl)sulfonyl]hexahydropyrrolo[1,2-a]pyrazin-6(2H)-one;
CAS Number	272786-64-8 ;
PubChem CID	9861054;
ChemSpider	8036753 ;
UNII	N4024LN29G;
ChEMBL	ChEMBL140717 ;
CompTox Dashboard (EPA)	DTXSID00432024 ;
Chemical and physical data
Formula	C13H15FN2O3S
Molar mass	298.333 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
	(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]

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

Safety

As of 2015^[update], no formal human studies with unifiram have been conducted.

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

Template:Nootropics

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

[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.

[pmid25831025-9] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]