Cebaracetam - Wikipedia

Cebaracetam
Clinical data

Other names	CGS-25248; ZY-15119
ATC code	None
Legal status
Legal status	US: Unscheduled and not FDA approved
Identifiers
IUPAC name 4-[2-[4-(4-Chlorophenyl)-2-oxopyrrolidin-1-yl]acetyl]piperazin-2-one
CAS Number	113957-09-8^Y
PubChem CID	65919
ChemSpider	59327^Y
UNII	Q25MNP6OC1
ChEMBL	ChEMBL2105942^Y
CompTox Dashboard (EPA)	DTXSID70869580
Chemical and physical data
Formula	C₁₆H₁₈ClN₃O₃
Molar mass	335.79 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CN(CC(=O)N1)C(=O)CN2CC(CC2=O)C3=CC=C(C=C3)Cl
InChI InChI=1S/C16H18ClN3O3/c17-13-3-1-11(2-4-13)12-7-15(22)20(8-12)10-16(23)19-6-5-18-14(21)9-19/h1-4,12H,5-10H2,(H,18,21)^N Key:QPKMIYNBZGPJAR-UHFFFAOYSA-N^N
(verify)

Cebaracetam (INNTooltip International Nonproprietary Name; developmental code names CGS-25248; ZY-15119) is an experimental drug of the racetam group described as a nootropic which was never marketed.^[1]^[2]^[3]

It is a chlorinated acetyl piperazine-substituted analogue of phenylpiracetam and is also a derivative of RGPU-95 (4-chlorophenylpiracetam).^[4] It is the analogue of RGPU-95 in which the terminal amide group has been replaced with a piperazin-2-one moiety.^[4] The mechanism of action of cebaracetam is undefined or unknown.^[1]

The drug was under development by Novartis for the treatment of cognition disorders by the 1990s but development was discontinued in 1995.^[1] It reached phase 2 clinical trials prior to its discontinuation.^[1]

References

[edit]

^ ^a ^b ^c ^d "Cebaracetam". AdisInsight. 23 May 1995. Retrieved 1 October 2024.
^ https://cdn.who.int/media/docs/default-source/international-nonproprietary-names-(inn)/stembook-2018.pdf
^ Chollet D, Künstner P (June 1992). "Fast systematic approach for the determination of drugs in biological fluids by fully automated high-performance liquid chromatography with on-line solid-phase extraction and automated cartridge exchange. Application to cebaracetam in human urine". Journal of Chromatography. 577 (2): 335–340. doi:10.1016/0378-4347(92)80255-o. PMID 1400764.
^ ^a ^b "Cebaracetam". PubChem. Retrieved 1 October 2024.

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 Anticonvulsants: Padsevonil

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

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