An AChE and butyrylcholinesterase inhibitor
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Active Metabolite(s)
18508Hydroxytacrine (maleate)
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Tacrine (hydrochloride)

Item No. 70240

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,2,3,4-tetrahydro-9-acridinamine, monohydrochloride
CAS Number
1684-40-8
Synonyms
  • C.I. 970
  • Hydroaminacrine
Molecular Formula
C13H14N2 • HCl
Formula Weight
234.7
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 33 mg/mlDMSO: 50 mg/mlEthanol: 20 mg/mlPBS (7.2): 16 mg/ml
λmax
243, 326, 339 nm
SMILES
NC1=C2C(CCCC2)=NC3=C1C=CC=C3.Cl
InChi Code
InChI=1S/C13H14N2.ClH/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);1H
InChi Key
ZUFVXZVXEJHHBN-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $40

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    5 g

    $129

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    Product Description

    Tacrine is a derivative of aminoacridine that functions as an inhibitor of both acetylcholinesterase (AChE) and butyrylcholinesterase (IC50s = 31 and 26.5 nM, respectively).1,2 Tacrine also inhibits the uptake of serotonin and norepinephrine in rat cerebral cortex and decreases depolarization-induced calcium influx through L-type calcium channels in SN56 neuronal cells.3,4,5 Formulations containing tacrine have been used clinically in the treatment of Alzheimer’s disease.3,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Crismon, M.L. Pharmacokinetics and drug interactions of cholinesterase inhibitors administered in Alzheimer’s disease. Pharmacotherapy 18(2 Pt. 2), 47-54 (1998).

    2. Ahmed, M., Rocha, J.B., Corrêa, M., et al. Inhibition of two different cholinesterases by tacrine. Chem. Biol. Interact. 162(2), 165-171 (2006).

    3. Drukarch, B., Leysen, J.E., and Stoof, J.C. Further analysis of the neuropharmacological profile of 9-amino-1,2,3,4-tetrahydroacridine (THA), an alleged drug for the treatment of Alzheimer’s disease. Life Sci. 42(9), 1011-1017 (1988).

    4. McKenna, M.T., Proctor, G.R., Young, L.C., et al. Novel tacrine analogues for potential use against Alzheimer’s disease: Potent and selective acetylcholinesterase inhibitors and 5-HT uptake inhibitors. J. Med. Chem. 40(22), 3516-3523 (1997).

    5. Dolezal, V., Lisá, V., and Tucek, S. Effect of tacrine on intracellular calcium in cholinergic SN56 neuronal cells. Brain Res. 769(2), 219-224 (1997).

    6. Giacobini, E. Cholinesterase inhibitors for Alzheimer’s disease therapy: From tacrine to future applications. Neurochem Int. 32(5-6), 413-419 (1998).

    Product Citations

    Tin, G., Mohamed, T., Gondora, N., et al. Tricyclic phenothiazine and phenoselenazine derivatives as potential multi-targeting agents to treat Alzheimer’s disease. Med. Chem. Comm. 6, 1930-1941 (2015).