Synonym
Devapamil; Devapamilum; Devapamilo
IUPAC/Chemical Name
2-(3,4-Dimethoxyphenyl)-2-isopropyl-5-((m-methoxyphenethyl)methylamino)valeronitrile
InChi Key
VMVKIDPOEOLUFS-UHFFFAOYSA-N
InChi Code
InChI=1S/C26H36N2O3/c1-20(2)26(19-27,22-11-12-24(30-5)25(18-22)31-6)14-8-15-28(3)16-13-21-9-7-10-23(17-21)29-4/h7,9-12,17-18,20H,8,13-16H2,1-6H3
SMILES Code
N#CC(C(C)C)(C1=CC=C(OC)C(OC)=C1)CCCN(CCC2=CC=CC(OC)=C2)C
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
424.59
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Schneider T, Regulla S, Hofmann F. The devapamil-binding site of the purified skeletal muscle receptor for organic-calcium channel blockers is modulated by micromolar and millimolar concentrations of Ca2+. Eur J Biochem. 1991 Aug 15;200(1):245-53. doi: 10.1111/j.1432-1033.1991.tb21073.x. PMID: 1652439.
2: Berjukov S, Aczel S, Beyer B, Kimball SD, Dichtl M, Hering S, Striessnig J. Extra- and intracellular action of quaternary devapamil on muscle L-type Ca(2+)-channels. Br J Pharmacol. 1996 Nov;119(6):1197-202. doi: 10.1111/j.1476-5381.1996.tb16022.x. PMID: 8937723; PMCID: PMC1915905.
3: Cheng RCK, Tikhonov DB, Zhorov BS. Structural model for phenylalkylamine binding to L-type calcium channels. J Biol Chem. 2009 Oct 9;284(41):28332-28342. doi: 10.1074/jbc.M109.027326. Epub 2009 Aug 21. PMID: 19700404; PMCID: PMC2788883.
4: Degtiar VE, Aczél S, Döring F, Timin EN, Berjukow S, Kimball D, Mitterdorfer J, Hering S. Calcium channel block by (-)devapamil is affected by the sequence environment and composition of the phenylalkylamine receptor site. Biophys J. 1997 Jul;73(1):157-67. doi: 10.1016/S0006-3495(97)78056-1. PMID: 9199780; PMCID: PMC1180917.
5: Erdmann R, Lüttgau HC. The effect of the phenylalkylamine D888 (devapamil) on force and Ca2+ current in isolated frog skeletal muscle fibres. J Physiol. 1989 Jun;413:521-41. doi: 10.1113/jphysiol.1989.sp017667. PMID: 2557440; PMCID: PMC1189114.
6: Wegener JW, Nawrath H. Extracellular site of action of phenylalkylamines on L-type calcium current in rat ventricular myocytes. Naunyn Schmiedebergs Arch Pharmacol. 1995 Sep;352(3):322-30. doi: 10.1007/BF00168564. PMID: 8584049.
7: Alican I, Toker F, Arbak S, Yegen BC, Yalçin AS, Oktay S. Gastric lipid peroxidation, glutathione and calcium channel blockers in the stress-induced ulcer model in rats. Pharmacol Res. 1994 Aug-Sep;30(2):123-35. doi: 10.1016/1043-6618(94)80004-9. PMID: 7816741.
8: Porzig H, Becker C. Potential-dependent allosteric modulation of 1,4-dihydropyridine binding by d-(cis)-diltiazem and (+/-)-verapamil in living cardiac cells. Mol Pharmacol. 1988 Aug;34(2):172-9. PMID: 2457793.
9: Schuster A, Lacinová L, Klugbauer N, Ito H, Birnbaumer L, Hofmann F. The IVS6 segment of the L-type calcium channel is critical for the action of dihydropyridines and phenylalkylamines. EMBO J. 1996 May 15;15(10):2365-70. PMID: 8665843; PMCID: PMC450166.
10: Ye Z, Van Dyke K. Reversal of chloroquine resistance in falciparum malaria by some calcium channel inhibitors and optical isomers is independent of calcium channel blockade. Drug Chem Toxicol. 1994;17(2):149-62. doi: 10.3109/01480549409014308. PMID: 8062642.
