Gallopamil

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]

Gallopamil

Clinical data
Other names	Methoxyverapamil
AHFS/Drugs.com	International Drug Names
ATC code	C08DA02 (WHO)
Identifiers
IUPAC name (RS)-5-[2-(3,4-Dimethoxyphenyl)ethyl-methylamino]-2-propan-2-yl-2-(3,4,5-trimethoxyphenyl)pentanenitrile
CAS Number	16662-47-8 Y HCl: 16662-46-7 Y
PubChem CID	1234
ChemSpider	1197 Y
UNII	39WPC8JHR8 HCl: VT4VR32A0T Y (HCl)
KEGG	D01969 Y
ChEMBL	ChEMBL51149 Y
CompTox Dashboard (EPA)	DTXSID5045172
Chemical and physical data
Formula	C28H40N2O5
Molar mass	484.637 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES 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

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

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.