Molsidomine

Molsidomine

Names
IUPAC name 1-Ethoxy-N-(3-morpholino-5-oxadiazol-3-iumyl)methanimidate
Identifiers
CAS Number	25717-80-0 Y
ChEMBL	ChEMBL1256353 N
ChemSpider	4090 Y
Jmol 3D model	Interactive image
KEGG	D01320 Y
PubChem	5353788
UNII	D46583G77X Y
InChI InChI=1S/C9H14N4O4/c1-2-16-9(14)10-8-7-13(11-17-8)12-3-5-15-6-4-12/h7H,2-6H2,1H3 Y Key: XLFWDASMENKTKL-UHFFFAOYSA-N Y InChI=1/C9H14N4O4/c1-2-16-9(14)10-8-7-13(11-17-8)12-3-5-15-6-4-12/h7H,2-6H2,1H3 Key: XLFWDASMENKTKL-UHFFFAOYAC
SMILES [O-]C(OCC)=Nc2on[n+](N1CCOCC1)c2
Properties
Chemical formula	C9H14N4O4
Molar mass	242.23 g/mol
Pharmacology
ATC code	C01DX12
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Molsidomine is an orally active, long acting vasodilating drug. Molsidomine is metabolized in the liver to the active metabolite linsidomine. Linsidomine is an unstable compound that releases nitric oxide (NO) upon decay as the actual vasodilating compound.

Release of nitric oxide

File:Activation of molsidomine.svg

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Chemistry

Molsidomine as well as linsidomine are sydnone imines, a class of mesoionic heterocyclic aromatic chemical compounds.

Synthesis

A mesoionic sydnone is active as an antianginal agent.

File:Molsidomine synthesis.svg

Molsidomine synthesis:

Its synthesis starts by reacting 1-aminomorpholine with formaldehyde and hydrogen cyanide to give 2. Nitrosation gives the N-nitroso analog (3) which cyclizes to the sydnone (4) on treatment with anhydrous acid. Formation of the ethyl urethane is then made possible by reacting Linsidomine with Ethyl chloroformate.

See also

• Nitric oxide
• Nitrate (pharmacology)
• Vasodilator