An NMDA receptor antagonist and antiviral agent
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Amantadine (hydrochloride)

Item No. 21364

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
tricyclo[3.3.1.13,7]decan-1-amine, monohydrochloride
CAS Number
665-66-7
Synonyms
  • Adamantylamine
  • Aminoadamantane
  • NSC 83653
Molecular Formula
C10H17N • HCl
Formula Weight
187.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 50 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
NC1(C[C@H](C2)C3)C[C@@H]2C[C@@H]3C1.Cl
InChi Code
InChI=1S/C10H17N.ClH/c11-10-4-7-1-8(5-10)3-9(2-7)6-10;/h7-9H,1-6,11H2;1H/t7-,8+,9-,10?;
InChi Key
WOLHOYHSEKDWQH-GFZFNSNDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 g

    $36

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    Cayman Chemical
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    Product Description

    Amantadine is an NMDA receptor antagonist with IC50 values of 0.93, 0.82, and 0.47 μM at -70 mV for NR1-1a/NR2A, NR1-1a/NR2B, and NR1-1a/NR2D subunit-containing recombinant receptors, respectively, expressed in HEK293 cells.1 It blocks the influenza A M2 proton channel (IC50 = 16 μM for the recombinant channel expressed in Xenopus oocytes) and inhibits cytotoxicity induced by the influenza A strains H1N1 and H3N2 in MDCK cells (EC50s = 34 and 0.84 μM, respectively).2 It also improves the survival of mice infected with influenza A when administered 24 hours following viral challenge at a dose of 100 mg/kg per day.3 Amantadine (40 mg/kg) decreases dyskinesia induced by L-DOPA (Item No. 13248) in a 6-OHDA hemi-parkinsonian mouse model.4 Formulations containing amantadine have been used in the treatment of various strains of influenza A virus infection and in the treatment of parkinsonism and drug-induced extrapyramidal symptoms.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bresink, I., Benke, T.A., Collett, V.J., et al. Effects of memantine on recombinant rat NMDA receptors expressed in HEK 293 cells. Br. J. Pharmacol. 119(2), 195-204 (1996).

    2. Rey-Carrizo, M., Torres, E., Ma, C., et al. 3-Azatetracyclo[5.2.1.15,8.01,5]undecane derivatives: From wild-type inhibitors of the M2 ion channel of influenza A virus to derivatives with potent activity against the V27A mutant. J. Med. Chem. 56(22), 9265-9274 (2013).

    3. Smee, D.F., Julander, J.G., Tarbet, E.B., et al. Treatment of oseltamivir-resistant influenza A (H1N1) virus infections in mice with antiviral agents. Antiviral Res. 96(1), 13-20 (2012).

    4. Bido, S., Marti, M., and Morari, M. Amantadine attenuates levodopa-induced dyskinesia in mice and rats preventing the accompanying rise in nigral GABA levels. J. Neurochem. 118(6), 1043-1055 (2011).