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Imolamine

Clinical data
Trade names	Angolon, Angoril, Circuline, Irri-Cor, Irrigor, Coremax
ATC code	C01DX09 (WHO)
Identifiers
IUPAC name Diethylamine
CAS Number	318-23-0 15823-89-9 (HCl)
PubChem CID	27501
DrugBank	DB09284
ChemSpider	10669810
UNII	K5F4RU5VQJ
KEGG	D07159
ChEMBL	ChEMBL2104282
CompTox Dashboard (EPA)	DTXSID00861870
ECHA InfoCard	100.005.699
Chemical and physical data
Formula	C14H20N4O
Molar mass	260.341 g·mol
3D model (JSmol)	Interactive image
SMILES CCN(CC)CCN2C(=N)O\N=C2\c1ccccc1
InChI 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 Key:MGSPDRWOUCPKNZ-UHFFFAOYSA-N
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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.

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Synthesis

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

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 KOH base occurs at the endocyclic ring nitrogen completing the synthesis of imolamine (6).

EFforts towards Onepot method (section 2.5 & 2.6).

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).

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