A class III antiarrhythmic agent
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Bretylium (tosylate)

Item No. 29979

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-bromo-N-ethyl-N,N-dimethyl-benzenemethanaminium, 4-methylbenzenesulfonate (1:1)
CAS Number
61-75-6
Molecular Formula
C11H17BrN • C7H7O3S
Formula Weight
414.4
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
220 nm
SMILES
BrC1=C(C[N+](C)(C)CC)C=CC=C1.CC2=CC=C(S([O-])(=O)=O)C=C2
InChi Code
InChI=1S/C11H17BrN.C7H8O3S/c1-4-13(2,3)9-10-7-5-6-8-11(10)12;1-6-2-4-7(5-3-6)11(8,9)10/h5-8H,4,9H2,1-3H3;2-5H,1H3,(H,8,9,10)/q+1;/p-1
InChi Key
KVWNWTZZBKCOPM-UHFFFAOYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $36

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    50 mg

    $153

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    100 mg

    $268

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    250 mg

    $502

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    Product Description

    Bretylium is a class III antiarrhythmic agent and an inhibitor of the Na+/K+-ATPase (IC50 = 4.5 mM).1 Bretylium also has antiadrenergic activity, inhibiting auricular nerve stimulation-induced vasoconstriction in isolated rabbit ears and hypogastric nerve stimulation-induced contraction of isolated rabbit uterus.2 It inhibits neuroeffector calcium transients (NCTs), as well as increases action potential delay and the absolute refractory period, but does not inhibit field stimulus-induced CTs in isolated mouse vas deferens sympathetic nerve terminals.3 Bretylium prevents ventricular fibrillation in anesthetized dogs in a model of sudden coronary death when administered at a dose of 10 mg/kg.4 Formulations containing bretylium were previously used in the prevention and treatment of ventricular fibrillation.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Helms, J.B., Arnett, K.L., Gatto, C., et al. Bretylium, an organic quaternary amine, inhibits the Na,K-ATPase by binding to the extracellular K-site. Blood Cells Mol. Dis. 32(3), 394-400 (2004).

    2. Boura, A.L., Copp, F.C., and Green, A.F. New antiadrenergic compounds. Nature 184, BA70-BA71 (1959).

    3. Brain, K.L., and Cunnane, T.C. Bretylium abolishes neurotransmitter release without necessarily abolishing the nerve terminal action potential in sympathetic terminals. Br. J. Pharmacol. 153(4), 831-839 (2007).

    4. Holland, K., Patterson, E., and Lucchesi, B.R. Prevention of ventricular fibrillation by bretylium in a conscious canine model of sudden coronary death. Am. Heart J. 105(5), 711-717 (1983).