Imolamine

Imolamine
Skeletal formula
Space-filling model
Clinical data
Trade namesAngolon, Angoril, Circuline, Irri-Cor, Irrigor, Coremax
ATC code
Identifiers
  • Diethyl[2-(5-imino-3-phenyl-4,5-dihydro-1,2,4-oxadiazol-4-yl)ethyl]amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.699 Edit this at Wikidata
Chemical and physical data
FormulaC14H20N4O
Molar mass260.341 g·mol−1
3D model (JSmol)
  • CCN(CC)CCN2C(=N)O\N=C2\c1ccccc1
  • InChI=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 X markN
  • Key:MGSPDRWOUCPKNZ-UHFFFAOYSA-N X markN
 X markNcheckY (what is this?)  (verify)

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.

Several patents describing its use have been issued.

Synthesis

Thieme Patent

The reaction of benzoylchloride oxime (2) with cyanamide (3) gives 3-phenyl-1,2,4-oxadiazol-5-amine (4). Alkylation with 2-chlorotriethylamine (5) in the presence of potassium hydroxide (KOH) occurs at the endocyclic ring nitrogen completing the synthesis of imolamine (6).

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

References

  1. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 547–. ISBN 978-3-88763-075-1.
  2. ↑ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 680–. ISBN 978-1-4757-2085-3.
  3. ↑ Anne Rolland, EP 0191253 (1986 to Laboratoires Albert Rolland SA).
  4. ↑ Anne Rolland, FR 2576789 (1986 to Laboratoires Albert Rolland SA).
  5. ↑ FR2023M idem J M D Aron-Samuel & J J Sterne, GB 1010231 (1965-11-17).