Tacrine

• CAT Number: I009680
• CAS Number: 321-64-2
• Molecular Formula: C13H14N2
• Molecular Weight: 198.26
• Purity: ≥95%
• Solubility: Soluble in DMSO, not in water
• Storage: 4°C, away from moisture and light
• IUPAC Name: 1,2,3,4-tetrahydroacridin-9-amine
• InChI: InChI=1S/C13H14N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1,3,5,7H,2,4,6,8H2,(H2,14,15)
• InChIKey: YLJREFDVOIBQDA-UHFFFAOYSA-N
• SMILES: C1CCC2=NC3=CC=CC=C3C(=C2C1)N

Tacrine（Cat No.:I009680）, is a pharmaceutical compound that was once used in the treatment of Alzheimer’s disease. It functions as a reversible acetylcholinesterase inhibitor, which means it increases the levels of acetylcholine in the brain, a neurotransmitter involved in memory and cognition. Tacrine was one of the earliest drugs approved for Alzheimer’s, offering modest cognitive improvements.

Reference

1:Cytochrome P450 binding studies of novel tacrine derivatives: Predicting the risk of hepatotoxicity. McEneny-King A, Osman W, Edginton AN, Rao PPN.Bioorg Med Chem Lett. 2017 Jun 1;27(11):2443-2449. doi: 10.1016/j.bmcl.2017.04.006. Epub 2017 Apr 3. PMID: 28400237 2:Design, synthesis and biological evaluation of multifunctional tacrine-curcumin hybrids as new cholinesterase inhibitors with metal ions-chelating and neuroprotective property. Liu Z, Fang L, Zhang H, Gou S, Chen L.Bioorg Med Chem. 2017 Apr 15;25(8):2387-2398. doi: 10.1016/j.bmc.2017.02.049. Epub 2017 Mar 6. PMID: 28302511 3:Tacrine-based Multifunctional Agents in Alzheimer/’s Disease: an Old Story in Continuous Development. Milelli A, De Simone A, Ticchi N, Chen HH, Betari N, Andrisano V, Tumiatti V.Curr Med Chem. 2017 Mar 9. doi: 10.2174/0929867324666170309123920. [Epub ahead of print] PMID: 28294041 4:Bis(3)-tacrine inhibits the sustained potassium current in cultured rat hippocampal neurons. Huang D, Wen RJ, Zhang Y, Liu YW.Physiol Res. 2017 Feb 28. [Epub ahead of print] PMID: 28248535 Free Article5:New tacrine-derived AChE/BuChE inhibitors: Synthesis and biological evaluation of 5-amino-2-phenyl-4H-pyrano[2,3-b]quinoline-3-carboxylates. Eghtedari M, Sarrafi Y, Nadri H, Mahdavi M, Moradi A, Homayouni Moghadam F, Emami S, Firoozpour L, Asadipour A, Sabzevari O, Foroumadi A.Eur J Med Chem. 2017 Mar 10;128:237-246. doi: 10.1016/j.ejmech.2017.01.042. Epub 2017 Feb 1. PMID: 28189905 6:Microwave assisted synthesis of novel hybrid tacrine-sulfonamide derivatives and investigation of their antioxidant and anticholinesterase activities. Ulus R, Zengin Kurt B, Gazioğlu I, Kaya M.Bioorg Chem. 2017 Feb;70:245-255. doi: 10.1016/j.bioorg.2017.01.005. Epub 2017 Jan 9. PMID: 28153340 7:Novel multitarget-directed tacrine derivatives as potential candidates for the treatment of Alzheimer/’s disease. Wu WY, Dai YC, Li NG, Dong ZX, Gu T, Shi ZH, Xue X, Tang YP, Duan JA.J Enzyme Inhib Med Chem. 2017 Dec;32(1):572-587. doi: 10.1080/14756366.2016.1210139. Review. PMID: 28133981 8:The pharmacology of tacrine at N-methyl-d-aspartate receptors. Horak M, Holubova K, Nepovimova E, Krusek J, Kaniakova M, Korabecny J, Vyklicky L, Kuca K, Stuchlik A, Ricny J, Vales K, Soukup O.Prog Neuropsychopharmacol Biol Psychiatry. 2017 Apr 3;75:54-62. doi: 10.1016/j.pnpbp.2017.01.003. Epub 2017 Jan 13. Review. PMID: 28089695 9:Tacrine-resveratrol fused hybrids as multi-target-directed ligands against Alzheimer/’s disease. Jeřábek J, Uliassi E, Guidotti L, Korábečný J, Soukup O, Sepsova V, Hrabinova M, Kuča K, Bartolini M, Peña-Altamira LE, Petralla S, Monti B, Roberti M, Bolognesi ML.Eur J Med Chem. 2017 Feb 15;127:250-262. doi: 10.1016/j.ejmech.2016.12.048. Epub 2016 Dec 26. PMID: 28064079 10:Tacrine: In vivo veritas. Jarrott B.Pharmacol Res. 2017 Feb;116:29-31. doi: 10.1016/j.phrs.2016.12.033. Epub 2016 Dec 28. PMID: 28040533