Nebracetam

Chemical compound

none

Legal statusLegal status

AU: S4 (Prescription only)
US: Unscheduled Not FDA approved

Identifiers

IUPAC name

(RS)-4-(Aminomethyl)-1-benzylpyrrolidin-2-one

CAS Number

97205-34-0^Y

PubChem CID

65926

ChemSpider

59334^Y

UNII

T30038QI8N

ChEMBL

ChEMBL2104682^N

CompTox Dashboard (EPA)

DTXSID00869598

Chemical and physical dataFormulaC₁₂H₁₆N₂OMolar mass204.273 g·mol⁻¹3D model (JSmol)

Interactive image

ChiralityRacemic mixture

SMILES

O=C2N(Cc1ccccc1)CC(C2)CN

InChI

InChI=1S/C12H16N2O/c13-7-11-6-12(15)14(9-11)8-10-4-2-1-3-5-10/h1-5,11H,6-9,13H2^Y
Key:LCAFGJGYCUMTGS-UHFFFAOYSA-N^Y

^NY (what is this?) (verify)

Nebracetam is an investigational drug of the racetam family that is a M₁ acetylcholine receptor agonist in rats.^[1] Based on a human leukemic T cell experiment in 1991, it is believed to act as an agonist for human M1-muscarinic receptors.^[2] It is also believed to act as a nootropic, like many other racetam drugs.^[3] A chemoenzymatic method of synthesis was reported in 2008.^[4] As of 2023^[update], human trials have not yet been conducted.

References

^ Takeo S, Hayashi H, Miyake K, Takagi K, Tadokoro M, Takagi N, et al. (June 1997). "Effects of delayed treatment with nebracetam on neurotransmitters in brain regions after microsphere embolism in rats". British Journal of Pharmacology. 121 (3): 477–484. doi:10.1038/sj.bjp.0701161. PMC 1564714. PMID 9179389.
^ Kitamura Y, Kaneda T, Nomura Y (January 1991). "Effects of nebracetam (WEB 1881 FU), a novel nootropic, as a M1-muscarinic agonist". Japanese Journal of Pharmacology. 55 (1): 177–180. doi:10.1254/jjp.55.177. PMID 2041225.
^ Gabryel B, Pudełko A, Trzeciak HI, Cieślik P (2000). "Effect of nebracetam on content of high-energy phosphates and morphometry of rat astrocytes in vitro. Comparison with piracetam". Acta Poloniae Pharmaceutica. 57 (4): 289–298. PMID 11126618.
^ Yamashita S, Mase N, Takabe K (2008-09-22). "Chemoenzymatic total synthesis and determination of the absolute configuration of (S)-nebracetam". Tetrahedron: Asymmetry. 19 (18): 2115–2118. doi:10.1016/j.tetasy.2008.09.004. ISSN 0957-4166.