Unifiram

Chemical compound From Wikipedia, the free encyclopedia

Unifiram (developmental code name DM-232) is an experimental drug.[1] that has antiamnesic and other effects in animal studies with far greater potency than piracetam.[2][3] A number of related compounds are known, such as sunifiram (DM-235) and sapunifiram (MN-19).[4][5][6] Unifiram has two enantiomers, with the dextro form being the more active isomer.[7] It has been shown to reduce the duration of hypnosis induced by pentobarbital, without impairing motor coordination.[8] As of 2015, no formal human studies with unifiram have been conducted. Unifiram is not patented and, despite the lack of human and long-term toxicity studies, it is commonly sold online.[9]

Other namesDM-232
Legal status
  • In general: unscheduled
Quick facts Clinical data, Other names ...
Unifiram
Skeletal formula
Ball-and-stick model of unifiram
Clinical data
Other namesDM-232
Legal status
Legal status
  • In general: unscheduled
Identifiers
  • 2-[(4-Fluorophenyl)sulfonyl]hexahydropyrrolo[1,2-a]pyrazin-6(2H)-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H15FN2O3S
Molar mass298.33 g·mol−1
3D model (JSmol)
  • C2CN1C(=O)CCC1CN2S(=O)(=O)c(cc3)ccc3F
  • 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 ☒N
  • Key:SNRTZFZAFBIBJP-UHFFFAOYSA-N ☒N
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Pharmacology

Unifiram, as well as sunifiram, were assayed at a wide panel of sites, including the most important receptors, ion channels, and transporters, but showed no affinity for any of the sites.[9][3] They specifically did not bind to the glutamate, GABA, serotonin, dopamine, adrenergic, histamine, acetylcholine, or opioid receptors at concentrations of up to 1 μM.[9][3] In addition, the drugs were tested on recombinant AMPA receptors and showed no potentiation of the receptors, indicating that they do not act as AMPA receptor positive allosteric modulators.[9] However, they were able to prevent the amnesia induced by the AMPA receptor antagonist NBQX in the passive avoidance test, suggesting that indirect/downstream AMPA receptor activation may be involved in their memory-enhancing effects.[3]

Chemistry

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

References

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