Anatabine dicitrate

• CAT Number: I045995
• Molecular Formula: C22H28N2O14
• Molecular Weight: 544.46
• Purity: ≥95%
• Synonyms: 2-hydroxypropane-1,2,3-tricarboxylic acid;3-[(2S)-1,2,3,6-tetrahydropyridin-2-yl]pyridine
• InChI: InChI=1S/C10H12N2.2C6H8O7/c1-2-7-12-10(5-1)9-4-3-6-11-8-9;2*7-3(8)1-6(13,5(11)12)2-4(9)10/h1-4,6,8,10,12H,5,7H2;2*13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t10-;;/m0../s1
• InChIKey: CGVRSINYLOUBAU-XRIOVQLTSA-N
• SMILES: C1C=CCNC1C2=CN=CC=C2.C(C(=O)O)C(CC(=O)O)(C(=O)O)O.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

Anatabine dicitrate is a tobacco alkaloid that can cross the blood-brain barrier. Anatabine dicitrate is a potent α4β2 nAChR agonist. Anatabine dicitrate inhibits NF-κB activation lower amyloid-β (Aβ) production by preventing the β-cleavage of amyloid precursor protein (APP). Anatabine dicitrate has anti-inflammatory effects and has the potential for neurodegenerative disorders treatment[1][2][3].
Anatabine (600 μg/mL; 24 hours; SHSY-5Y cells) treatment shows an inhibition of p65 NF-κB phosphorylation[1].
Anatabine (500-1000μg/mL; 30 minutes; SHSY-5Y cells) treatment fully prevents the increase in BACE-1 mRNA levels induced by TNF-α. After 24 hours, Anatabine treatment shows a dose-dependent inhibition of BACE-1 protein levels[1].
Anatabine dose dependently inhibits Aβ1-40 and Aβ1-42 with an approximate half maximal inhibitory concentration of 640 μg/mL for both Aβ1-40 and Aβ1-42 in 7W CHO cells. Anatabine inhibits sAPPβ secretion without impacting sAPPα suggesting that Anatabine is preventing the β-cleavage of amyloid precursor protein (APP)[1].
Anatabine (0.5-2 mg/kg; intraperitoneal injection; daily; for 4 days; transgenic mouse) treatment significantly lowers brain soluble Aβ1-40 and Aβ1-42 levels in a transgenic mouse model of Alzheimer’s disease[1].

Reference

[1]. Paris D, et al. Anatabine lowers Alzheimer’s Aβ production in vitro and in vivo. Eur J Pharmacol. 2011 Nov 30;670(2-3):384-91.
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[2]. Xing H, et al. A Pharmacological Comparison of Two Isomeric Nicotinic Receptor Agonists: The Marine Toxin Isoanatabine and the Tobacco Alkaloid Anatabine. Mar Drugs. 2020 Feb 11;18(2). pii: E106.
 [Content Brief]

[3]. eo EJ, et al. Phytochemicals as inhibitors of NF-κB for treatment of Alzheimer’s disease. Pharmacol Res. 2018 Mar;129:262-273.
 [Content Brief]