A calcium channel inhibitor
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Prenylamine

Item No. 29430

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(1-methyl-2-phenylethyl)-γ-phenyl-benzenepropanamine
CAS Number
390-64-7
Molecular Formula
C24H27N
Formula Weight
329.5
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: slightly solubleMethanol: slightly soluble
SMILES
CC(NCCC(C1=CC=CC=C1)C2=CC=CC=C2)CC3=CC=CC=C3
InChi Code
InChI=1S/C24H27N/c1-20(19-21-11-5-2-6-12-21)25-18-17-24(22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,20,24-25H,17-19H2,1H3
InChi Key
IFFPICMESYHZPQ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $49

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    10 mg

    $93

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    50 mg

    $423

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    100 mg

    $748

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    Product Description

    Prenylamine is a calcium channel inhibitor.1 It inhibits the plasma membrane Ca2+ ATPase (PMCA) in isolated and purified pig cardiac sarcolemma.2 It binds to a hydrophobic site on calcium-bound calmodulin (CaM) with a Kd value of 0.5 µM and inhibits CaM-activated cAMP phosphodiesterase (PDE) activity when used at concentrations ranging from 10 to 50 µM, an effect that is negatively associated with the concentration of calmodulin.2,3 Prenylamine (30 μM) shortens action potential duration and decreases the amplitude of peak calcium currents in single guinea pig ventricular myocytes in the absence and presence of propranolol (Item No. 23349) and phentolamine (Item No. 16135).4 Prenylamine (50 mg/kg) decreases epinephrine, serotonin, and dopamine levels in rat brain.5 It also decreases epinephrine levels in rat heart. It protects anesthetized rats from coronary artery occlusion-induced arrhythmia when administered at a dose of 0.5 mg/kg but increases mortality due to atrioventricular block leading to asystole when administered at a dose of 5 mg/kg.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bayer, R., Schwarzmaier, J., and Pernice, R. Basic mechanisms underlying prenylamine-induced 'torsade de pointes': Differences between prenylamine and fendiline due to basic actions of the isomers. Curr. Med. Res. Opin. 11(4), 254-272 (1988).

    2. Lamers, J.M., Cysouw, K.J., and Verdouw, P.D. Slow calcium channel blockers and calmodulin. Effect of felodipine, nifedipine, prenylamine and bepridil on cardiac sarcolemmal calcium pumping ATPase. Biochem. Pharmacol. 34(21), 3837-3843 (1985).

    3. Johnson, J.D., and Wittenauer, L.A. A fluorescent calmodulin that reports the binding of hydrophobic inhibitory ligands. Biochem. J. 211(2), 473-479 (1983).

    4. Shimoni, Y., Posner, P., Spindler, A.J., et al. The effects of prenylamine on single ventricular myocytes of guinea-pig. Br. J. Pharmacol. 94(2), 319-324 (1988).

    5. Obianwu, H.O. The effect of prenylamine (segontin®) on the amine levels of brain, heart and adrenal medulla in rats. Acta. Pharmacol. Toxicol. (Copenh) 23(4), 383-390 (1965).

    6. Fagbemi, O., Kane, K.A., McDonald, F.M., et al. The effects of verapamil, prenylamine, flunarizine and cinnarizine on coronary artery occlusion-induced arrhythmias in anaesthetized rats. Br. J. Pharmacol. 83(1), 299-304 (1984).