User:Persept/sandbox

Persept/sandbox
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	Unscheduled (US);
Identifiers
	IUPAC name N-(2,6-dimethylphenyl)-2-(2-oxopyrrolidin-1-yl)acetamide ;
CAS Number	77191-36-7 ;
PubChem CID	71157;
ChemSpider	64299 ;
UNII	1JK12GX30N;
ChEMBL	ChEMBL260829 ;
Chemical and physical data
Formula	C14H18N2O2
Molar mass	246.305 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2N(CC(=O)Nc1c(cccc1C)C)CCC2;
	InChI InChI=1S/C14H18N2O2/c1-10-5-3-6-11(2)14(10)15-12(17)9-16-8-4-7-13(16)18/h3,5-6H,4,7-9H2,1-2H3,(H,15,17) ; Key:NGHTXZCKLWZPGK-UHFFFAOYSA-N ;
	(what is this?) (verify)

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Nefiracetam is a nootropic antidementia drug of the racetam family.^[1]

Nefiracetam's cytoprotective actions are mediated by enhancement of GABAergic, cholinergic, and monoaminergic neuronal systems that give antiamnesia effects to the Alzheimer's type and cerebrovascular type of dementia.^[2]^[3]

Concerns

Animals which metabolize nefiracetam differently than humans and primates are at risk for renal ^[4]^[5] and testicular ^[6] ^[7] toxicity. Dogs especially are particularly sensitive, which has been shown to be caused by a specific metabolite, M-18^[5]. Higher doses than those in dogs were needed to cause testicular toxicity in rats, although no toxicity [9] and [10]., however, was seen in monkeys. Additionally, there has been no evidence of toxicity during clinical trials ^[8]^[9] <ref name=Shimomura>

References

^ Murphy, Keith (22 July 2004). "Chronic Exposure of Rats to Cognition Enhancing Drugs Produces a Neuroplastic response" (PDF). Neuropsychopharmacology. Retrieved 1 September 2010.
^ Robinson RG, Jorge RE, Clarence-Smith K, Starkstein S (2009). "Double-blind treatment of apathy in patients with poststroke depression using nefiracetam". The Journal of Neuropsychiatry and Clinical Neurosciences. 21 (2): 144–51. doi:10.1176/appi.neuropsych.21.2.144. PMID 19622685.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Robinson RG, Jorge RE, Clarence-Smith K (2008). "Double-blind randomized treatment of poststroke depression using nefiracetam". The Journal of Neuropsychiatry and Clinical Neurosciences. 20 (2): 178–84. doi:10.1176/appi.neuropsych.20.2.178. PMID 18451188.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Cite error: The named reference Tsuchiya was invoked but never defined (see the help page).
^ ^a ^b Goto, Koichi; Ishii, Yoshikazu; Jindo, Toshimasa; Furuhama, Kazuhisa (3). "Effect of Nefiracetam, a Neurotransmission Enhancer, on Primary Uroepithelial Cells of the Canine Urinary Bladder". Toxicological Sciences. 1 (72): 164–70. doi:10.1093/toxsci/kfg010. PMID 12604846. {{cite journal}}: Check date values in: |date= and |year= / |date= mismatch (help); Unknown parameter |month= ignored (help)
^ Shimada, M; Shikanai, Y; Shimomura, K; Harada, S; Watanabe, G; Taya, K; Kato, M; Furuhama, K (2003). "Investigation of testicular toxicity of nefiracetam, a neurotransmission enhancer, in rats". Toxicology Letters. 143 (3): 307–15. doi:10.1016/s0378-4274(03)00197-8. PMID 12849691.
^ Shimomura, K; Shimada, M; Hagiwara, M; Harada, S; Kato, M; Furuhama, K (2004). "Testicular toxicity induced in dogs by nefiracetam, a neutrotransmission enhancer". Reproductive Toxicology (Elmsford, N.Y.). 18 (3): 423–30. doi:10.1016/j.reprotox.2004.01.008. PMID 15082078.
^ M Murasaki, M Inami, J Ishigooka, H Watanabe, M Utsumi, T Matsumoto; et al. (1994). "Phase I study on DM-9384 (nefiracetam)". Jpn. Pharmacol. Ther. 22: 3539–3587. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
^ E Otomo, K Kogure, S Hirai, F Goto, K Hasegawa, Y Tazaki; et al. (1994). "Clinical evaluation of DM-9384 in the treatment of cerebrovascular disorders: early phase II study". Jpn. Pharmacol. Ther. (22): 3589–3624. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)

Category:Racetams Category:Pyrrolidones Category:Acetanilides Category:Nootropics

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[NPP2005-1] Murphy, Keith (22 July 2004). "Chronic Exposure of Rats to Cognition Enhancing Drugs Produces a Neuroplastic response" (PDF). Neuropsychopharmacology. Retrieved 1 September 2010.

[2] Robinson RG, Jorge RE, Clarence-Smith K, Starkstein S (2009). "Double-blind treatment of apathy in patients with poststroke depression using nefiracetam". The Journal of Neuropsychiatry and Clinical Neurosciences. 21 (2): 144–51. doi:10.1176/appi.neuropsych.21.2.144. PMID 19622685.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[3] Robinson RG, Jorge RE, Clarence-Smith K (2008). "Double-blind randomized treatment of poststroke depression using nefiracetam". The Journal of Neuropsychiatry and Clinical Neurosciences. 20 (2): 178–84. doi:10.1176/appi.neuropsych.20.2.178. PMID 18451188.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[Tsuchiya-4] Cite error: The named reference Tsuchiya was invoked but never defined (see the help page).

[Goto-5] Goto, Koichi; Ishii, Yoshikazu; Jindo, Toshimasa; Furuhama, Kazuhisa (3). "Effect of Nefiracetam, a Neurotransmission Enhancer, on Primary Uroepithelial Cells of the Canine Urinary Bladder". Toxicological Sciences. 1 (72): 164–70. doi:10.1093/toxsci/kfg010. PMID 12604846. {{cite journal}}: Check date values in: |date= and |year= / |date= mismatch (help); Unknown parameter |month= ignored (help)

[6] Shimada, M; Shikanai, Y; Shimomura, K; Harada, S; Watanabe, G; Taya, K; Kato, M; Furuhama, K (2003). "Investigation of testicular toxicity of nefiracetam, a neurotransmission enhancer, in rats". Toxicology Letters. 143 (3): 307–15. doi:10.1016/s0378-4274(03)00197-8. PMID 12849691.

[Shimomura-7] Shimomura, K; Shimada, M; Hagiwara, M; Harada, S; Kato, M; Furuhama, K (2004). "Testicular toxicity induced in dogs by nefiracetam, a neutrotransmission enhancer". Reproductive Toxicology (Elmsford, N.Y.). 18 (3): 423–30. doi:10.1016/j.reprotox.2004.01.008. PMID 15082078.

[8] M Murasaki, M Inami, J Ishigooka, H Watanabe, M Utsumi, T Matsumoto; et al. (1994). "Phase I study on DM-9384 (nefiracetam)". Jpn. Pharmacol. Ther. 22: 3539–3587. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)

[9] E Otomo, K Kogure, S Hirai, F Goto, K Hasegawa, Y Tazaki; et al. (1994). "Clinical evaluation of DM-9384 in the treatment of cerebrovascular disorders: early phase II study". Jpn. Pharmacol. Ther. (22): 3589–3624. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)

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[3]

[4]

[5]

[6]

[7]

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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

Concerns

See also

References