Gallopamil
Calcium channel blocker drug
- C08DA02 (WHO)
- (RS)-5-[2-(3,4-Dimethoxyphenyl)ethyl-methylamino]-2-propan-2-yl-2-(3,4,5-trimethoxyphenyl)pentanenitrile
- 16662-47-8
Y
- HCl: 16662-46-7
Y
- 1234
- 1197
Y
- 39WPC8JHR8
- HCl: VT4VR32A0T
Y (HCl)
- D01969
Y
- ChEMBL51149
Y
- DTXSID5045172
- Interactive image
- N#CC(c1cc(OC)c(OC)c(OC)c1)(CCCN(CCc2ccc(OC)c(OC)c2)C)C(C)C
InChI
- InChI=1S/C28H40N2O5/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
Y
- Key:XQLWNAFCTODIRK-UHFFFAOYSA-N
Y
Gallopamil (INN) is an L-type calcium channel blocker that is an analog of verapamil. It is used in the treatment of abnormal heart rhythms.[1]
Synthesis
The alkylation reaction of 3,4,5-trimethoxyphenylacetonitrile (1) and isopropyl chloride (2), using sodium amide as base gives the intermediate nitrile (3). A second alkylation with a specific alkyl chloride (4) yields gallopamil.[2][3][4]
References
- ^ Sewing KF, Hannemann H (1983). "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. doi:10.1159/000137824. PMID 6310646.
- ^ US patent 4115432, Dengel, Ferdinand, "Method for making basically-substituted phenylacetonitriles", issued 1978-09-19, assigned to Knoll GmbH
- ^ Theodore LJ, Nelson WL (1987). "Stereospecific synthesis of the enantiomers of verapamil and gallopamil". The Journal of Organic Chemistry. 52 (7): 1309–1315. doi:10.1021/jo00383a026.
- ^ "Gallopamil". Thieme. Retrieved 2024-07-02.
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VGKCsTooltip Voltage-gated potassium channels |
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IRKsTooltip Inwardly rectifying potassium channel |
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KCaTooltip Calcium-activated potassium channel |
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K2PsTooltip Tandem pore domain potassium channel |
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VGSCsTooltip Voltage-gated sodium channels |
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ENaCTooltip Epithelial sodium channel |
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ASICsTooltip Acid-sensing ion channel |
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CaCCsTooltip Calcium-activated chloride channel |
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CFTRTooltip Cystic fibrosis transmembrane conductance regulator |
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Unsorted |
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TRPsTooltip Transient receptor potential channels |
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LGICsTooltip Ligand gated ion channels |
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See also: Receptor/signaling modulators • Transient receptor potential channel modulators
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