Dupracetam

Dupracetam
Clinical data
ATC code	none;
Legal status
Legal status	In general: unscheduled;
Identifiers
	IUPAC name 2-(2-oxopyrrolidin-1-yl)-N'-[2-(2-oxopyrrolidin-1-yl)acetyl]acetohydrazide;
CAS Number	59776-90-8 ;
PubChem CID	68793;
ChemSpider	62033 ;
UNII	BVM2UGN450;
ChEMBL	ChEMBL2104359 ;
CompTox Dashboard (EPA)	DTXSID40975187 ;
ECHA InfoCard	100.056.279
Chemical and physical data
Formula	C12H18N4O4
Molar mass	282.300 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC(=O)N(C1)CC(=O)NNC(=O)CN2CCCC2=O;
	InChI InChI=1S/C12H18N4O4/c17-9(7-15-5-1-3-11(15)19)13-14-10(18)8-16-6-2-4-12(16)20/h1-8H2,(H,13,17)(H,14,18) ; Key:YPUPYVWSTBYCBY-UHFFFAOYSA-N ;
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Dupracetam is a nootropic drug from the racetam family.^[1]^[2]

One of its metabolites, 1-Methylhydantoin, displays renal toxicity in high doses.^[3]

References

^ Dell HD, Jacobi H, Kamp R, Kurz J, Wünsche C (August 1981). "[1-Methylhydantoin, an unexpected metabolite of the intelligence-affecting substance dupracetam (author's transl)]". Archiv der Pharmazie (in German). 314 (8): 697–702. doi:10.1002/ardp.19813140808. PMID 7294979. S2CID 95603731.
^ Hall ED, Von Voigtlander PF (November 1987). "Facilitatory effects of piracetam on excitability of motor nerve terminals and neuromuscular transmission". Neuropharmacology. 26 (11): 1573–1579. doi:10.1016/0028-3908(87)90003-7. PMID 2829047. S2CID 7759558.
^ Yang B, Liu D, Li CZ, Liu FY, Peng YM, Jiang YS (2007). "1-Methylhydantoin cytotoxicity on renal proximal tubular cells in vitro". Renal Failure. 29 (8): 1025–1029. doi:10.1080/08860220701641272. PMID 18067051. S2CID 26843776.

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v t Racetams
Racetams	Nootropics: Aniracetam Coluracetam Dimiracetam Doliracetam Dupracetam Fasoracetam Imuracetam Nebracetam Nefiracetam Nicoracetam Oxiracetam Piperacetam Piracetam Pramiracetam Rolipram Rolziracetam Anticonvulsants: Brivaracetam Etiracetam Levetiracetam Seletracetam
Phenylpiracetams	Nootropics and/or stimulants: Cebaracetam Methylphenylpiracetam E1R ((4R,5S)-methylphenylpiracetam) Phenylpiracetam (phenotropil; fonturacetam) MRZ-9547 ((R)-phenylpiracetam) (S)-Phenylpiracetam RGPU-95 (chlorophenylpiracetam) Anticonvulsants: Phenylpiracetam hydrazide
Racetam-like	Nootropics: Aloracetam Molracetam Omberacetam (Noopept) Tenilsetam Traneurocin (cycloprolylglycine; NA-831) Anticonvulsants: Padsevonil