nebracetam

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 447117038

| IUPAC_name = (RS)-4-(Aminomethyl)-1-benzylpyrrolidin-2-one

| image = Nebracetam.svg

| width = 150px

| image2 = Nebracetam3d.png

| chirality = Racemic mixture

| tradename =

| pregnancy_category =

| legal_AU = S4

| legal_US = unscheduled

| legal_US_comment = Not FDA approved

| routes_of_administration =

| bioavailability =

| metabolism =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 97205-34-0

| ATC_prefix = none

| PubChem = 65926

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104682

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 59334

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = T30038QI8N

| C=12 | H=16 | N=2 | O=1

| smiles = O=C2N(Cc1ccccc1)CC(C2)CN

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LCAFGJGYCUMTGS-UHFFFAOYSA-N

}}

Nebracetam is an investigational drug of the racetam family that is a M₁ acetylcholine receptor agonist in rats.{{cite journal | vauthors = Takeo S, Hayashi H, Miyake K, Takagi K, Tadokoro M, Takagi N, Oshikawa S | title = Effects of delayed treatment with nebracetam on neurotransmitters in brain regions after microsphere embolism in rats | journal = British Journal of Pharmacology | volume = 121 | issue = 3 | pages = 477–484 | date = June 1997 | pmid = 9179389 | pmc = 1564714 | doi = 10.1038/sj.bjp.0701161 }} Based on a human leukemic T cell experiment in 1991, it is believed to act as an agonist for human M1-muscarinic receptors.{{cite journal | vauthors = Kitamura Y, Kaneda T, Nomura Y | title = Effects of nebracetam (WEB 1881 FU), a novel nootropic, as a M1-muscarinic agonist | journal = Japanese Journal of Pharmacology | volume = 55 | issue = 1 | pages = 177–180 | date = January 1991 | pmid = 2041225 | doi = 10.1254/jjp.55.177 | doi-access = free }} It is also believed to act as a nootropic, like many other racetam drugs.{{cite journal | vauthors = Gabryel B, Pudełko A, Trzeciak HI, Cieślik P | title = Effect of nebracetam on content of high-energy phosphates and morphometry of rat astrocytes in vitro. Comparison with piracetam | journal = Acta Poloniae Pharmaceutica | volume = 57 | issue = 4 | pages = 289–298 | date = 2000 | pmid = 11126618 | url = https://pubmed.ncbi.nlm.nih.gov/11126618/ }} A chemoenzymatic method of synthesis was reported in 2008.{{Cite journal | vauthors = Yamashita S, Mase N, Takabe K |date=2008-09-22 |title=Chemoenzymatic total synthesis and determination of the absolute configuration of (S)-nebracetam |journal=Tetrahedron: Asymmetry |volume=19 |issue=18 |pages=2115–2118 |doi=10.1016/j.tetasy.2008.09.004 |issn=0957-4166}} {{As of|2023}}, human trials have not yet been conducted.