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Gallopamil

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Gallopamil
Clinical data
Other namesMethoxyverapamil
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • (RS)-5-[2-(3,4-Dimethoxyphenyl)ethyl-methylamino]-2-propan-2-yl-2-(3,4,5-trimethoxyphenyl)pentanenitrile
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H40N2O5
Molar mass484.637 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • N#CC(c1cc(OC)c(OC)c(OC)c1)(CCCN(CCc2ccc(OC)c(OC)c2)C)C(C)C
  • 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 checkY
  • Key:XQLWNAFCTODIRK-UHFFFAOYSA-N checkY

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

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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

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  1. ^ 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.
  2. ^ US patent 4115432, Dengel, Ferdinand, "Method for making basically-substituted phenylacetonitriles", issued 1978-09-19, assigned to Knoll GmbH 
  3. ^ 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.
  4. ^ "Gallopamil". Thieme. Retrieved 2024-07-02.