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bis(7)-Tacrine
Cayman Chemical Item Number 10005836
Description
Tacrine is an amino acridine compound that inhibits acetylcholinesterase (AChE), and has been proposed as a clinical treatment for Alzheimer’s disease.1↗ bis(7)-Tacrine is a tacrine dimer, linked via a 7-carbon alkyl spacer. It inhibits AChE with an IC50 of 0.40 nM, making it more than 1,000 times more potent than tacrine.2↗ bis(7)-Tacrine also protects against hydrogen peroxide induced apoptosis in rat pheochromocytoma cells.3↗
1 Giacobini, E. Cholinesterase inhibitors for Alzheimer’s disease therapy: From tacrine to future applications. Neurochem Int 32 413-419 (1998).
2 Carlier, P.R., Han, Y.F., Chow, E.S.H., et al. Evaluation of short-tether Bis-THA AChE inhibitors. A further test of the dual binding site hypothesis. Bioorg Med Chem 7 351-357 (1999).
3 Hong, W., Carlier, P.R., Wing-Lok, H., et al. Attenuation of scopolamine-induced deficits in navigational memory performance in rats by bis(7)-tacrine, a novel dimeric AChE inhibitor. Acta Pharmacol Sin 20(3) 211-217 (1999).
Synonyms 1,7-N-heptylene-bis-9,9'-amino-1,2,3,4-tetrahydro-acridine
Formal Name N,N'-bis(1,2,3,4-tetrahydro-9-acridinyl)-1,7-heptanediamine, dihydrochloride
CAS Number 224445-12-9
Molecular Formula C33H40N4 · 2HCl
Formula Weight 565.6
Formulation A crystalline solid
Purity >98%
λmax 223, 247, 338, 351 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES [H]N(CCCCCCCN([H])C1=C(C=CC=C2)C2=NC3=C1CCCC3)C4=C5C(C=CC=C5)=NC6=C4CCCC6.[·2HCl]
InCHI Code 1S/C33H40N4.2ClH/c1(2-12-22-34-32-24-14-4-8-18-28(24)36-29-19-9-5-15-25(29)32)3-13-23-35-33-26-16-6-10-20-30(26)37-31-21-11-7-17-27(31)33;;/h4,6,8,10,14,16,18,20H,1-3,5,7,9,11-13,15,17,19,21-23H2,(H,34,36)(H,35,37);2*1H
InCHI Key RHKXINFBJWDTSK-UHFFFAOYSA-N |