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

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, Oshikawa S (June 1997). "Effects of delayed treatment with nebracetam on neurotransmitters in brain regions after microsphere embolism in rats". British Journal of Pharmacology. 121 (3): 477–84. 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. ISSN 0021-5198. PMID 2041225.
^ Gabryel, B.; Pudełko, A.; Trzeciak, H. I.; 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. ISSN 0001-6837. PMID 11126618.
^ Yamashita, Sho; Mase, Nobuyuki; Takabe, Kunihiko (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.