SEN 12333 / WAY-317,538, ≥98%

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SEN 12333 ≥98
Chemical Name: N-[4-(3-Pyridinyl)phenyl]-4-morpholinepentanamide

Synonyms: 5-morpholin-4-ylpentanoic acid (4-pyridin-3-ylphenyl)amide, WAY-317,538

CAS #: 874450-44-9

Dual agonist at α7 nAChRs / antagonist at histamine H3 receptors with cognition enhancing and neuroprotective properties.

Form: Cream yellow powder
Molecular Formula: C20H25N3O2•½H2O

Molecular Weight:    348.44 g/mol

Solubility:    Soluble in DMSO.

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Precaution and Disclaimer:

This Material is Sold For Research Use Only. Terms of Sale Apply. Not for Human Consumption, nor Medical, Veterinary, or Household Uses.

Chemical Information:

CAS Number:874450-44-9
Purity:≥98%
Molecular Weight:348.44 g/mol
Melting Point:Unknown
Molecular Formula:C20H25N3O2•½H2O
Synonyms: WAY-317538, SureCN676043, CHEMBL1084615, CHEBI:731814, SEN12333, SEN-12333, WAY 317538, WAY-317,538, N-[4-(3-Pyridinyl)phenyl]-4-morpholinepentanamide, 874450-44-9
PubChem CID:45484303
SMILES:C1COCCN1CCCCC(=O)NC2=CC=C(C=C2)C3=CN=CC=C3

Technical Information:

Application:Dual agonist at α7 nAChRs / antagonist at histamine H3 receptors with cognition enhancing and neuroprotective properties.
Appearance:Cream yellow powder
Physical State:Solid
Solubility:Soluble in DMSO
Storage:Store at room temperature or cooler, in a sealed airtight container, protected from heat, light and humidity.
Stability:Stable for at least two years when stored as above.

Biochemical Activity:

SEN12333 / WAY-317538 is a novel dual α7 nicotinic acetylcholine receptor (nAChR) agonist (EC50 = 1.6 μM, Ki = 260 nM at rat α7 nAChRs) and histamine H3 receptor antagonist (IC50 = 103 nM)1. SEN12333 was found to be neuroprotective in a rodent model of quisqualic acid-induced cholinergic degeneration, to be brain penetrant and to possess oral bioavailability[2].

SEN12333 was chosen to be evaluated in in vivo efficacy models based on its generally good in vitro profile, ease of synthesis, and selectivity on a related panel of nicotinic (α1, α3, α4β2) and highly homologous receptors (5HT3A). This was confirmed in a panel of 70 binding sites including all major classes of neurotransmitter, growth factor and peptide receptors whereby no significant activity was observed when the compound was tested at 10 µM concentration, except for the histamine H3 receptor where binding was observed leading to receptor antagonism. SEN12333 also showed minimal hERG inhibition, desirable drug-like (molecular weight, number of rotatable bonds, log P, polar surface area) and pharmacokinetic properties.[1]

In vivo, SEN12333/WAY-317538 improved performance in rodent behavioural assays of cognitive function and perceptual processing, producing enhancement of normal memory performance[2].

References:

  • [1] Haydar SN, Ghiron C, Bettinetti L, Bothmann H, Comery TA, Dunlop J, La Rosa S, Micco I, Pollastrini M, Quinn J, Roncarati R, Scali C, Valacchi M, Varrone M, Zanaletti R. (2009). "SAR and biological evaluation of SEN12333/WAY-317538: Novel alpha 7 nicotinic acetylcholine receptor agonist." Bioorg Med Chem. 17(14):5247-58. doi: 10.1016/j.bmc.2009.05.040 PMID: 19515567
  • [2] Roncarati R, Scali C, Comery TA, Grauer SM, Aschmi S, Bothmann H, Jow B, Kowal D, Gianfriddo M, Kelley C, Zanelli U, Ghiron C, Haydar S, Dunlop J, Terstappen GC. (2009). "Procognitive and neuroprotective activity of a novel alpha7 nicotinic acetylcholine receptor agonist for treatment of neurodegenerative and cognitive disorders." J Pharmacol Exp Ther. 329(2):459-68. doi: 10.1124/jpet.108.150094 PMID: 19223665

Precaution and Disclaimer:

This Material is Sold For Research Use Only. Terms of Sale Apply. Not for Human Consumption, nor Medical, Veterinary, or Household Uses.