An L-type calcium channel blocker
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Labeled Version(s)
18452(±)-Verapamil-d3 (hydrochloride)
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Verapamil (hydrochloride)

Item No. 14288

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
α-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)-benzeneacetonitrile, monohydrochloride
CAS Number
152-11-4
Synonyms
  • NSC 272366
  • NSC 657799
  • (±)-Verapamil
Molecular Formula
C27H38N2O4 • HCl
Formula Weight
491.1
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 16.7 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 0.25 mg/ml
λmax
205, 231, 280 nm
SMILES
COC1=CC=C(C(C(C)C)(C#N)CCCN(C)CCC2=CC=C(OC)C(OC)=C2)C=C1OC.Cl
InChi Code
InChI=1S/C27H38N2O4.ClH/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6;/h9-12,17-18,20H,8,13-16H2,1-7H3;1H
InChi Key
DOQPXTMNIUCOSY-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 g

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    Product Description

    Verapamil is the prototypical blocker of L-type calcium channels that produces excitation-contraction uncoupling in cardiac muscle by preventing the slow-inward current of calcium ions.1 Verapamil can also block calcium fluxes in vascular smooth muscle. It has both peripheral and coronary vasodilator effects (IC50 = 0.38 μM in guinea pig aortic strip) and has been used to control hypertension, angina, cardiac arrhythmia, and vascular headaches.2,3,4 Verapamil has also been used in cell biology as an inhibitor of drug efflux pump proteins such as P-glycoprotein, which are often over-expressed in certain tumor cell lines.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Singh, B.N. The mechanism of action of calcium antagonists relative to their clinical applications. Br. J. Clin. Pharmacol. 21(Suppl 2), 109S-121S (1986).

    2. Dei, S., Romanelli, M.N., Scapecchi, S., et al. Verapamil analogues with restricted molecular flexibility: Synthesis and pharmacological evaluation of the four isomers of α-[1-[3-[N-[1-[2-(3,4-dimethoxy-phenyl)ethyl]]-N-methylamino]cyclohexyl]]-α-isopropyl-3,4-dimethoxybenzene-acetonitrile. J. Med. Chem. 36(4), 439-445 (1993).

    3. Dawson, J.R., Whitaker, N.H., and Sutton, G.C. Calcium antagonist drugs in chronic stable angina. Comparison of verapamil and nifedipine. Br. Heart J. 46(5), 508-512 (2013).

    4. Campbell, T.J., and Williams, K.M. Therapeutic drug monitoring: Antiarrhythmic drugs. Br. J. Clin. Pharmacol. 46(4), 307-319 (1998).

    5. Rabindran, S.K., He, H., Singh, M., et al. Reversal of a novel multidrug resistance mechanism in human colon carcinoma cells by fumitremorgin C. Cancer Res. 58(24), 5850-5858 (1998).

    Product Citations

    Rana, P.S., Gibbons, B.A., Vereninov, A.A., et al. Calibration and characterization of intracellular Asante Potassium Green probes, APG-2 and APG-4. Anal. Biochem. 567, 8-13 (2019).

    Hirano, Y., Yoshida, M., Shimizu, M., et al. Direct demonstration of rapid degradation of nuclear sterol regulatory element-binding proteins by the ubiquitin-proteasome pathway. The Journal of Biological Chemisty 276(39), 36431-36437 (2001).