gallopamil
{{Short description|Calcium channel blocker drug}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| IUPAC_name = (RS)-5-[2-(3,4-Dimethoxyphenyl)ethyl-methylamino]-2-propan-2-yl-2-(3,4,5-trimethoxyphenyl)pentanenitrile
| image = Gallopamil.png
| chirality = Racemic mixture
| tradename =
| Drugs.com = {{drugs.com|international|gallopamil}}
| pregnancy_AU =
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| index2_label = HCl
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 16662-47-8
| CAS_number2_Ref = {{cascite|correct|CAS}}
| CAS_number2 = 16662-46-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 39WPC8JHR8
| UNII2_Ref = {{fdacite|correct|FDA}} (HCl)
| UNII2 = VT4VR32A0T
| ATC_prefix = C08
| ATC_suffix = DA02
| ATC_supplemental =
| PubChem = 1234
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D01969
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 51149
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1197
| smiles = N#CC(c1cc(OC)c(OC)c(OC)c1)(CCCN(CCc2ccc(OC)c(OC)c2)C)C(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XQLWNAFCTODIRK-UHFFFAOYSA-N
| synonyms = Methoxyverapamil
| chemical_formula =
| C=28 | H=40 | N=2 | O=5
}}
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.{{cite journal | vauthors = Sewing KF, Hannemann H | title = Calcium channel antagonists verapamil and gallopamil are powerful inhibitors of acid secretion in isolated and enriched guinea pig parietal cells | journal = Pharmacology | volume = 27 | issue = 1 | pages = 9–14 | year = 1983 | pmid = 6310646 | doi = 10.1159/000137824 | url = http://content.karger.com/ProdukteDB/produkte.asp?Aktion=ShowAbstractBuch&ArtikelNr=137824&ProduktNr=236614) }}
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.{{cite patent |country=US |number=4115432 |title=Method for making basically-substituted phenylacetonitriles |inventor=Dengel, Ferdinand |status=patent |gdate=1978-09-19 |fdate=1977-07-05 |assign1=Knoll GmbH }}{{cite journal |doi=10.1021/jo00383a026 |title=Stereospecific synthesis of the enantiomers of verapamil and gallopamil |date=1987 | vauthors = Theodore LJ, Nelson WL |journal=The Journal of Organic Chemistry |volume=52 |issue=7 |pages=1309–1315 }}{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-07-0006 |title=Gallopamil |publisher=Thieme |access-date=2024-07-02}}
References
{{reflist}}
{{Calcium channel blockers}}
Category:Calcium channel blockers
Category:Methoxyphenethylamines
{{cardiovascular-drug-stub}}