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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| protein_bound =
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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.
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:Diethylamino compounds
{{cardiovascular-drug-stub}}