An L-type channel blocker
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(±)-Methoxyverapamil (hydrochloride)

Item No. 24270

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
α-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4,5-trimethoxy-α-(1-methylethyl)-benzeneacetonitrile, monohydrochloride
CAS Number
16662-46-7
Synonyms
  • Gallopamil
  • NSC 274966
Molecular Formula
C28H40N2O5 • HCl
Formula Weight
521.1
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
281, 305 nm
SMILES
COC1=C(OC)C=C(C(C(C)C)(C#N)CCCN(C)CCC2=CC=C(OC)C(OC)=C2)C=C1OC.Cl
InChi Code
InChI=1S/C28H40N2O5.ClH/c1-20(2)28(19-29,22-17-25(33-6)27(35-8)26(18-22)34-7)13-9-14-30(3)15-12-21-10-11-23(31-4)24(16-21)32-5;/h10-11,16-18,20H,9,12-15H2,1-8H3;1H
InChi Key
OKCRIUNHEQSXFD-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    50 mg

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    Product Description

    (±)-Methoxyverapamil is a phenylalkylamine L-type calcium channel blocker and methoxy derivative of verapamil (Item No. 14288).1 (±)-Methoxyverapamil blocks recombinant rat L-type calcium channels expressed in tsA201 cells with IC50 values of 782 and 8,000 nM at holding potentials of 10 and -60 mV, respectively. It blocks maitotoxin-induced calcium influx in NIH3T3 fibroblasts (IC50 = 16 μM) and inhibits histamine-induced acid secretion in primary enriched guinea pig parietal cells (IC50 = 10.9 μM).2,3 (±)-Methoxyverapamil binds to rat myocardial membranes (IC50 = 16 nM) and inhibits electrically-stimulated contractions in rat right myocardial ventricular strips (EC50 = 1.95 μM).4 In conscious, ovariectomized, post-partum rats, it decreases blood pressure by 30 mm Hg and induces 60% inhibition of uterine contractions when administered at doses of 204 and 324 μg/kg, respectively.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Johnson, B.D., Hockerman, G.H., Scheuer, T., et al. Distinct effects of mutations in transmembrane segment IVS6 on block of L-type calcium channels by structurally similar phenylalkylamines. Mol. Pharmacol. 50(5), 1388-1400 (1996).

    2. Daly, J.W., Lueders, J., Padgett, W.L., et al. Maitotoxin-elicited calcium influx in cultured cells. Effect of calcium-channel blockers. Biochem. Pharmacol. 50(8), 1187-1197 (1995).

    3. Sewing, K.F., and Hannemann, H. Calcium channel antagonists verapamil and gallopamil are powerful inhibitors of acid secretion in isolated and enriched guinea pig parietal cells. Pharmacology 27(1), 9-14 (1983).

    4. Theodore, L.J., Nelson, W.L., Zobrist, R.H., et al. Studies on Ca2+ channel antagonists. 5-[(3,4-Dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2- isopropylpentyl isothiocyanate, a chemoaffinity ligand derived from verapamil. J. Med. Chem. 29(9), 1789-1792 (1986).

    5. Abel, M.H., and Hollingsworth, M. The potencies and selectivities of four calcium antagonists as inhibitors of uterine contractions in the rat in vivo. Br. J. Pharmacol. 85(1), 263-269 (1985).