Gallopamil

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 ; HCl: 16662-46-7 ;
PubChem CID	1234;
ChemSpider	1197 ;
UNII	39WPC8JHR8; HCl: VT4VR32A0T (HCl);
KEGG	D01969 ;
ChEMBL	ChEMBL51149 ;
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 ; Key:XQLWNAFCTODIRK-UHFFFAOYSA-N ;
	(what is this?) (verify)

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

Thieme ChemDrug Synthesis:^[2]^[3]^[4] Patent:^[5]^[6] Sep optical antipodes:^[7]

The alkylation between 3,4,5-Trimethoxyphenylacetonitrile [13338-63-1] (1)and 2-chloropropane [75-29-6] (2) gives 3-Methyl-2-(3,4,5-trimethoxyphenyl)butanenitrile [36622-33-0] (3). Treatment with N-Methyl-N-(3-Chloropropyl)Homoveratrylamine [36770-74-8] (4) completed the synthesis of Gallopamil (5).

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.
^ Mannhold, R.; Gallopamil Hydrochloride. Drugs Fut 1984, 9, 2, 108.
^ Theodore, Louis J.; Nelson, Wendel L. (1987). "Stereospecific synthesis of the enantiomers of verapamil and gallopamil". The Journal of Organic Chemistry. 52 (7): 1309–1315. doi:10.1021/jo00383a026.
^ https://caod.oriprobe.com/articles/28518495/Synthesis_of_Gallopamil_Hydrochloride.htm
^ Ferdinand Dengel, US4115432 (1978 to Knoll GmbH).
^ Werner Seitz, Klaus Scheib, & Alfred Michel, US4418017 (1983 to BASF SE).
^ Siegfried Herrling, US4305887 (1981 to BASF SE).

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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] Mannhold, R.; Gallopamil Hydrochloride. Drugs Fut 1984, 9, 2, 108.

[3] Theodore, Louis J.; Nelson, Wendel L. (1987). "Stereospecific synthesis of the enantiomers of verapamil and gallopamil". The Journal of Organic Chemistry. 52 (7): 1309–1315. doi:10.1021/jo00383a026.

[4] ttps://caod.oriprobe.com/articles/28518495/Synthesis_of_Gallopamil_Hydrochloride.htm

[5] Ferdinand Dengel, US4115432 (1978 to Knoll GmbH).

[6] Werner Seitz, Klaus Scheib, & Alfred Michel, US4418017 (1983 to BASF SE).

[7] Siegfried Herrling, US4305887 (1981 to BASF SE).

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