An internal standard for the quantification of verapamil (hydrochloride)
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Unlabeled Version(s)
14288Verapamil (hydrochloride)
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(±)-Verapamil-d3 (hydrochloride)

Item No. 18452

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
α-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methyl-d3-amino]propyl]-3,4-dimethoxy-α-(1-methylethyl)-benzeneacetonitrile
CAS Number
2714485-49-9
Molecular Formula
C27H35D3N2O4 • HCl
Formula Weight
494.1
Purity
≥99% deuterated forms (d1-d3)
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mLDMSO: 10 mg/mLEthanol: 10 mg/mLPBS (pH 7.2): 0.25 mg/mL
SMILES
COC1=CC=C(C(C(C)C)(C#N)CCCN(C([2H])([2H])[2H])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/i3D3;
InChi Key
DOQPXTMNIUCOSY-FJCVKDQNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    1 mg

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    Product Description

    (±)-Verapamil-d3 (hydrochloride) (Item No. 18452) is intended for use as an internal standard for the quantification of verapamil (Item No. 14288) by GC- or LC-MS. 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).