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 =

| pregnancy_US =

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| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

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| routes_of_administration =

| bioavailability =

| protein_bound =

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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

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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.{{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