Imolamine

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 445965485

| IUPAC_name = Diethyl[2-(5-imino-3-phenyl-4,5-dihydro-1,2,4-oxadiazol-4-yl)ethyl]amine

| image = Imolamine.png

| width = 120px

| alt = Skeletal formula

| image2 = Imolamine-3D-spacefill.png

| alt2 = Space-filling model

| tradename = Angolon, Angoril, Circuline, Irri-Cor, Irrigor, Coremax

| pregnancy_AU =

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 318-23-0

| CAS_supplemental =
{{CAS|15823-89-9}} (HCl)

| ATC_prefix = C01

| ATC_suffix = DX09

| PubChem = 27501

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB09284

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104282

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = K5F4RU5VQJ

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07159

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 10669810

| C=14 | H=20 | N=4 | O=1

| smiles = CCN(CC)CCN2C(=N)O\N=C2\c1ccccc1

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C14H20N4O/c1-3-17(4-2)10-11-18-13(16-19-14(18)15)12-8-6-5-7-9-12/h5-9,15H,3-4,10-11H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = MGSPDRWOUCPKNZ-UHFFFAOYSA-N

}}

Imolamine (INN, BAN; brand names Angolon, Angoril, Circuline, Irri-Cor, Irrigor, Coremax) is a coronary vasodilator which is used in the treatment of angina pectoris and as a local anesthetic.{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA547|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=547–}}{{cite book | vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA680|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=680–}}

Use patents:Anne Rolland, {{Cite patent|EP|0191253}} (1986 to Laboratoires Albert Rolland SA).Anne Rolland, {{Cite patent|FR|2576789}} (1986 to Laboratoires Albert Rolland SA).

Synthesis

Butalamine has very similar synthesis but is alkylated on the alternate nitrogen position.

File:Imolamine synthesis.svg

The reaction of benzoylchloride oxime [698-16-8] (2) with Cyanamide (3) gives 3-Phenyl-1,2,4-oxadiazol-5-amine [3663-37-4] (4). Alkylation with 2-chlorotriethylamine [100-35-6] (5) in the presence of KOH base occurs at the endocyclic ring nitrogen completing the synthesis of imolamine (6).

EFforts towards [https://eprints.lincoln.ac.uk/id/eprint/28632/ Onepot method] (section 2.5 & 2.6).

References

{{Reflist}}

{{Vasodilators used in cardiac diseases}}

{{Local anesthetics}}

Category:Local anesthetics

Category:Oxadiazoles

Category:Vasodilators

Category:Diethylamino compounds

{{cardiovascular-drug-stub}}