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31059-54-8

31059-54-8 structure
31059-54-8 structure
  • Name: α-NETA
  • Chemical Name: <2-(2-naphthoyl)ethyl>trimethylammonium iodide
  • CAS Number: 31059-54-8
  • Molecular Formula: C16H20INO
  • Molecular Weight: 369.241
  • Catalog: Signaling Pathways Apoptosis Apoptosis
  • Create Date: 2018-02-13 21:04:51
  • Modify Date: 2025-08-27 10:55:46
  • α-NETA is a stable, noncompetitive, slowly reversible choline acetyltransferase (ChAT) inhibitor with an IC50 of 9 μM. α-NETA is a potent chemokine-like receptor-1 (CMKLR1) antagonist. α-NETA weakly inhibits cholinesterase (IC50=84 µM) and acetylcholinesterase (IC50=300 µM). α-NETA has anti-cancer activity[1][2].

Name <2-(2-naphthoyl)ethyl>trimethylammonium iodide
Synonyms N,N,N-Trimethyl-3-(1-naphthyl)-3-oxopropan-1-aminium iodide
iodide
N,N,N-Trimethyl-3-(1-naphthyl)-3-oxo-1-propanaminium iodide
[2-(2-naphthoyl)ethyl]trimethylammonium iodide
Trimethyl-(3-naphthalen-2-yl-3-oxo-propyl)-ammonium
1-Naphthalenepropanaminium, N,N,N-trimethyl-γ-oxo-, iodide (1:1)
3-Dimethylamino-propionaphtonmethoiodid
α-NETA
Description α-NETA is a stable, noncompetitive, slowly reversible choline acetyltransferase (ChAT) inhibitor with an IC50 of 9 μM. α-NETA is a potent chemokine-like receptor-1 (CMKLR1) antagonist. α-NETA weakly inhibits cholinesterase (IC50=84 µM) and acetylcholinesterase (IC50=300 µM). α-NETA has anti-cancer activity[1][2].
Related Catalog
Target

IC50: 9 μM (ChAT); CMKLR1; 84 µM (cholinesterase); 300 µM (acetylcholinesterase)[1][2]

In Vitro a-NETA (50-150 nM; 24 hours) decreases all cell lines viability in a dose-dependent manner [3]. a-NETA (2.5-10.0 µg/mL; 24 hours) leads to epithelial ovarian cancer (EOC) cell death associated with membrane blistering and cytoplasm leakage[3]. a-NETA treatment increases EOC cell expression of pyroptosis-associated proteins[3]. Cell Viability Assay[3] Cell Line: Ho8910, Ho8910PM, A2780, and Iose80 cells Concentration: 50, 100, 150 nM Incubation Time: 24 hours Result: Decreased all cell lines viability in a dose-dependent manner. Apoptosis Analysis[3] Cell Line: Epithelial ovarian cancer (EOC) cell Concentration: 2.5, 7.5, 10.0 µg/mL Incubation Time: 24 hours Result: Led to EOC cell death associated with membrane blistering and cytoplasm leakage.
In Vivo a-NETA (injected intraperitoneally; 0.125 mg/kg; once every other day for 20 days) significantly decreases tumor volume and tumor weight[3]. a-NETA (s.c. injection; 3 mg/kg or 10 mg/kg; daily; for 30 days) significantly delays the onset of EAE with 3 mg/kg, and completely suppresses clinical signs for an average of nine days with 10 mg/kg beyond the first appearance of disease in control female C57BL/6 mice[2]. Animal Model: BALB/c nude mice with skov3 cells[3] Dosage: 0.125 mg/kg Administration: Injected intraperitoneally; once every other day for 20 days Result: Significantly decreased tumor volume and tumor weight.
References

[1]. Sastry BV, et al. Relationships between chemical structure and inhibition of choline acetyltransferase by 2-(alpha-naphthoyl)ethyltrimethylammonium and related compounds. Pharmacol Res Commun. 1988 Sep;20(9):751-71.

[2]. Graham KL, et al. A novel CMKLR1 small molecule antagonist suppresses CNS autoimmune inflammatory disease. PLoS One. 2014 Dec 1;9(12):e112925.

[3]. Qiao L, et al. α-NETA induces pyroptosis of epithelial ovarian cancer cells through the GSDMD/caspase-4 pathway. FASEB J. 2019 Nov;33(11):12760-12767.

Molecular Formula C16H20INO
Molecular Weight 369.241
Exact Mass 369.058960
PSA 17.07000
LogP 4.11700
Hazard Codes Xi
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