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Imolamine

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Chemical compound

Pharmaceutical compound

Imolamine
Clinical data


Trade names	Angolon, Angoril, Circuline, Irri-Cor, Irrigor, Coremax
ATC code	C01DX09 (WHO)
Identifiers
IUPAC name Diethyl[2-(5-imino-3-phenyl-4,5-dihydro-1,2,4-oxadiazol-4-yl)ethyl]amine
CAS Number	318-23-0^N 15823-89-9 (HCl)
PubChemCID	27501
DrugBank	DB09284^Y
ChemSpider	10669810^N
UNII	K5F4RU5VQJ
KEGG	D07159^Y
ChEMBL	ChEMBL2104282^N
CompTox Dashboard(EPA)	DTXSID00861870
ECHA InfoCard	100.005.699
Chemical and physical data
Formula	C₁₄H₂₀N₄O
Molar mass	260.341 g·mol⁻¹
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^N Key:MGSPDRWOUCPKNZ-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

Imolamine (INN,BAN; brand namesAngolon,Angoril,Circuline,Irri-Cor,Irrigor,Coremax) is acoronary vasodilator which is used in the treatment ofangina pectoris and as alocal anesthetic.^[1]^[2]

Use patents:^[3]^[4]

Synthesis

[edit]

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

The reaction of benzoylchloride oxime [698-16-8] (2) withCyanamide (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 towardsOnepot method (section 2.5 & 2.6).

References

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^Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 547–.ISBN 978-3-88763-075-1.
^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.
^Anne Rolland,EP 0191253 (1986 to Laboratoires Albert Rolland SA).
^Anne Rolland,FR 2576789 (1986 to Laboratoires Albert Rolland SA).
^FR2023M idem J M D Aron-Samuel & J J Sterne,GB 1010231 (1965-11-17).

v t e Vasodilators used incardiac diseases (C01D)
Nitrovasodilators	Nitroglycerin # Isosorbide dinitrate # Isosorbide mononitrate Itramin tosilate Linsidomine Molsidomine Nicorandil Pentaerythritol tetranitrate Propatylnitrate Tenitramine Trolnitrate
Quinolone vasodilators	Flosequinan^‡
Others	Benziodarone Carbocromen Cinepazet Cloridarol Dilazep Efloxate Etafenone Gapicomine Heptaminol Hexobendine Imolamine Levosimendan Nesiritide Nicorandil Oxyfedrine Pimobendan Prenylamine Serelaxin Trapidil Vericiguat
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Local anesthetics(primarilysodium channel blockers) (N01B)

Esters by acid

Aminobenzoic	Benzocaine Benzonatate Butacaine Butamben Chloroprocaine Dimethocaine Lucaine Meprylcaine Metabutethamine Metabutoxycaine Nitracaine Orthocaine Propoxycaine Procaine (Novocaine) Proxymetacaine Risocaine Tetracaine
Benzoic	Amylocaine Cocaine Cyclomethycaine α-Eucaine β-Eucaine Hexylcaine Isobucaine Piperocaine
ArCO2- (not para-amino or Ph)	Amoproxan (3,4,5-Trimethoxybenzoyl) 3-(p-Fluorobenzoyloxy)tropane

Amides

Combinations

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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