Nebracetam

Nebracetam
Clinical data
ATC code	none;
Legal status
Legal 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 ;
PubChem CID	65926;
ChemSpider	59334 ;
UNII	T30038QI8N;
ChEMBL	ChEMBL2104682 ;
CompTox Dashboard (EPA)	DTXSID00869598 ;
Chemical and physical data
Formula	C12H16N2O
Molar mass	204.273 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic 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 ; Key:LCAFGJGYCUMTGS-UHFFFAOYSA-N ;
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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.

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v t e 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

Clinical data


ATC code	none
Legal status
Legal 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 data
Formula	C₁₂H₁₆N₂O
Molar mass	204.273 g·mol⁻¹
3D model (JSmol)	Interactive image
Chirality	Racemic 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)