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WAY-317538

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Chemical compound

Pharmaceutical compound

WAY-317538
Legal status

Legal status	In general: legal
Identifiers
IUPAC name 5-Morpholin-4-yl-pentanoic acid (4-pyridin-3-yl-phenyl)-amide
CAS Number	874450-44-9^N
PubChemCID	45484303 HCl: 45484302
ChemSpider	24663034^N
UNII	M92TU1EZ75
ChEMBL	ChEMBL1084615^N HCl: ChEMBL565540^N
CompTox Dashboard(EPA)	DTXSID30670437
Chemical and physical data
Formula	C₂₀H₂₅N₃O₂
Molar mass	339.439 g·mol⁻¹
3D model (JSmol)	Interactive image HCl: Interactive image
SMILES C3COCCN3CCCCC(=O)Nc1ccc(cc1)-c2cccnc2 HCl: C1COCCN1CCCCC(=O)NC2=CC=C(C=C2)C3=CN=CC=C3.Cl
InChI InChI=1S/C20H25N3O2/c24-20(5-1-2-11-23-12-14-25-15-13-23)22-19-8-6-17(7-9-19)18-4-3-10-21-16-18/h3-4,6-10,16H,1-2,5,11-15H2,(H,22,24)^N Key:XCHIZTUBUXZESJ-UHFFFAOYSA-N^N HCl: InChI=1S/C20H25N3O2.ClH/c24-20(5-1-2-11-23-12-14-25-15-13-23)22-19-8-6-17(7-9-19)18-4-3-10-21-16-18;/h3-4,6-10,16H,1-2,5,11-15H2,(H,22,24);1H Key:GBMDUJQQSGOIFW-UHFFFAOYSA-N
^NY (what is this?) (verify)

WAY-317538 (SEN-12333) is a drug that acts as a potent and selectivefull agonist for theα7 subtype of neuralnicotinic acetylcholine receptors. It was not the most potent compound in the series, but was selected for further development on the basis of its high selectivity over related receptors, ease of synthesis, and goodin vivo properties including high oral bioavailability and good brain penetration.^[1] It hasnootropic andneuroprotective effects in animal studies, and is being investigated as a potential treatment for neurodegenerative and neurocognitive conditions includingAlzheimer's disease andschizophrenia.^[2]

References

[edit]

^Haydar SN, Ghiron C, Bettinetti L, Bothmann H, Comery TA, Dunlop J, et al. (July 2009). "SAR and biological evaluation of SEN12333/WAY-317538: Novel alpha 7 nicotinic acetylcholine receptor agonist".Bioorganic & Medicinal Chemistry.17 (14):5247–58.doi:10.1016/j.bmc.2009.05.040.PMID 19515567.
^Roncarati R, Scali C, Comery TA, Grauer SM, Aschmi S, Bothmann H, et al. (May 2009). "Procognitive and neuroprotective activity of a novel alpha7 nicotinic acetylcholine receptor agonist for treatment of neurodegenerative and cognitive disorders".The Journal of Pharmacology and Experimental Therapeutics.329 (2):459–68.doi:10.1124/jpet.108.150094.PMID 19223665.S2CID 6667145.

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Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine,Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA (Dextrodopa,Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine,Levofenfluramine) Fenproporex Feprosidnine Fludorex Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine,Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Pyr-AI Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
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Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472
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ATC code:N06B

Nicotinic acetylcholine receptor modulators

nAChRsTooltip Nicotinic acetylcholine receptors

Agonists
(and PAMsTooltip positive allosteric modulators)

Antagonists
(and NAMsTooltip negative allosteric modulators)

Precursors
(andprodrugs)

See also: Receptor/signaling modulators; Muscarinic acetylcholine receptor modulators; Acetylcholine metabolism/transport modulators

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