Product Name

  • Name

    Molsidomine

  • EINECS 247-207-4
  • CAS No. 25717-80-0
  • Article Data3
  • CAS DataBase
  • Density 1.3186 (rough estimate)
  • Solubility
  • Melting Point 140-141 °C
  • Formula C9H14N4O4
  • Boiling Point 385.05°C (rough estimate)
  • Molecular Weight 242.235
  • Flash Point
  • Transport Information
  • Appearance colorless or white crystalline powder
  • Safety 36
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 25717-80-0 (Molsidomine)
  • Hazard Symbols HarmfulXn
  • Synonyms Sydnoneimine, N-(ethoxycarbonyl)-3-(4-morpholinyl)-;Sydnone imine, N-carboxy-3-morpholino-,ethyl ester (8CI);CAS 276;Corraton;Coruno;Corvasal;Corvaton;Molsidolat;1,2,3-Oxadiazolium,5-[(ethoxycarbonyl)amino]-3-(4-morpholinyl)-, inner salt;Morial;Morsydomine;Motazomin;N-(Ethoxycarbonyl)-3-morpholinosydnone imine;N-Ethoxycarbonyl-3-morpholinosydnonimine;SIN 10;SIN 10 (pharmaceutical);Sydnopharm;
  • PSA 82.09000
  • LogP -0.43350

Synthetic route

4-lithiomolsidomine

4-lithiomolsidomine

molsidomine
25717-80-0

molsidomine

Conditions
ConditionsYield
With water100%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

Linsidomine hydrochloride
16142-27-1

Linsidomine hydrochloride

molsidomine
25717-80-0

molsidomine

Conditions
ConditionsYield
With sodium hydrogencarbonate
molsidomine
25717-80-0

molsidomine

4-lithiomolsidomine

4-lithiomolsidomine

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran; tetrahydrofuran-d8 Inert atmosphere;100%
sulfur
10544-50-0

sulfur

molsidomine
25717-80-0

molsidomine

mercury dichloride

mercury dichloride

bis((6-ethoxycarbonyl-3-morpholinyl-sydnone imine-4-yl)thio)mercury(II)

bis((6-ethoxycarbonyl-3-morpholinyl-sydnone imine-4-yl)thio)mercury(II)

Conditions
ConditionsYield
Stage #1: molsidomine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: sulfur In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #3: mercury dichloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;		88%
...Expand
triphenylborane
960-71-4

triphenylborane

molsidomine
25717-80-0

molsidomine

(5-ethylcarbamate-3-morpholinyl-1,2,3-oxadiazolium-4-yl)triphenylborate

(5-ethylcarbamate-3-morpholinyl-1,2,3-oxadiazolium-4-yl)triphenylborate

Conditions
ConditionsYield
Stage #1: molsidomine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: triphenylborane In tetrahydrofuran at -10 - 20℃; for 4h; Inert atmosphere;		87%
molsidomine
25717-80-0

molsidomine

methyl iodide
74-88-4

methyl iodide

6-ethoxycarbonyl-4-methylthio-3-morpholinyl sydnone imine

6-ethoxycarbonyl-4-methylthio-3-morpholinyl sydnone imine

Conditions
ConditionsYield
Stage #1: molsidomine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With sulfur In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #3: methyl iodide In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere;		85%
molsidomine
25717-80-0

molsidomine

mercury dichloride

mercury dichloride

bis(6-ethoxycarbonyl-3-morpholinyl-sydnone imine-4-yl)mercury(II)

bis(6-ethoxycarbonyl-3-morpholinyl-sydnone imine-4-yl)mercury(II)

Conditions
ConditionsYield
Stage #1: molsidomine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: mercury dichloride In tetrahydrofuran at 0 - 20℃; for 3.5h; Inert atmosphere;		78%
molsidomine
25717-80-0

molsidomine

ethyl-N-(1-morpholinyl-1-thioxo-ethan-2-one)carbamate

ethyl-N-(1-morpholinyl-1-thioxo-ethan-2-one)carbamate

Conditions
ConditionsYield
Stage #1: molsidomine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With sulfur In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere;
Stage #3: With water In tetrahydrofuran Inert atmosphere;		63%
sulfur
10544-50-0

sulfur

(triphenylphosphine)gold(I) chloride
14243-64-2

(triphenylphosphine)gold(I) chloride

molsidomine
25717-80-0

molsidomine

((6-ethoxycarbonyl-3-morpholinyl-sydnone imine-4-yl)thio)(triphenylphosphine)gold(I)

((6-ethoxycarbonyl-3-morpholinyl-sydnone imine-4-yl)thio)(triphenylphosphine)gold(I)

Conditions
ConditionsYield
Stage #1: molsidomine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: sulfur In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #3: (triphenylphosphine)gold(I) chloride In tetrahydrofuran at 0 - 20℃; for 3.5h; Inert atmosphere;		36%
...Expand
molsidomine
25717-80-0

molsidomine

morpholine
110-91-8

morpholine

Conditions
ConditionsYield
In methanol for 0.166667h; Product distribution; Kinetics; Irradiation; var. of solvent, also additives;
molsidomine
25717-80-0

molsidomine

peracetylated β-cyclodextrin
23739-88-0

peracetylated β-cyclodextrin

C9H14N4O4*C84H112O56

C9H14N4O4*C84H112O56

Conditions
ConditionsYield
With carbon dioxide at 45℃; under 258776 Torr; for 0.5h;
molsidomine
25717-80-0

molsidomine

trans-chloro(N3-morpholinyl-N6-ethylestersydnonimine-4-yl)bis(triphenylphosphine)palladium(II)

trans-chloro(N3-morpholinyl-N6-ethylestersydnonimine-4-yl)bis(triphenylphosphine)palladium(II)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hexamethyldisilazane / tetrahydrofuran-d8; tetrahydrofuran / Inert atmosphere
2: tetrahydrofuran / -50 - 20 °C / Inert atmosphere
View Scheme
molsidomine
25717-80-0

molsidomine

C9H13(2)HN4O4

C9H13(2)HN4O4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hexamethyldisilazane / tetrahydrofuran-d8; tetrahydrofuran / Inert atmosphere
2: [D3]acetonitrile / 20 °C
View Scheme
molsidomine
25717-80-0

molsidomine

4-(methylseleno)molsidomine

4-(methylseleno)molsidomine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran-d8; tetrahydrofuran / Inert atmosphere
2.1: selenium / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
2.2: 0 - 20 °C / Inert atmosphere
View Scheme
molsidomine
25717-80-0

molsidomine

(N3-morpholinyl-N6-ethoxycarbonyl-sydnonimine-4-yl)(triphenylphosphine)gold(I)

(N3-morpholinyl-N6-ethoxycarbonyl-sydnonimine-4-yl)(triphenylphosphine)gold(I)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hexamethyldisilazane / tetrahydrofuran-d8; tetrahydrofuran / Inert atmosphere
2: tetrahydrofuran / -50 - 20 °C / Inert atmosphere
View Scheme
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

molsidomine
25717-80-0

molsidomine

4-[(4'-chlorophenyl)hydroxymethyl]-3-morpholyl-N6-ethoxycarbonylsydnone imine

4-[(4'-chlorophenyl)hydroxymethyl]-3-morpholyl-N6-ethoxycarbonylsydnone imine

Conditions
ConditionsYield
Stage #1: molsidomine With n-butyllithium In tetrahydrofuran; hexane at -80 - 20℃; for 0.35h;
Stage #2: 4-chlorobenzaldehyde In tetrahydrofuran; hexane at 20℃; for 0.333333h; Reagent/catalyst; Time;
1-methoxy-N,N-dimethylmethanaminium methylsulphate

1-methoxy-N,N-dimethylmethanaminium methylsulphate

molsidomine
25717-80-0

molsidomine

4-formyl-3-morpholino-N6-ethoxycarbonylsydnone imine

4-formyl-3-morpholino-N6-ethoxycarbonylsydnone imine

Conditions
ConditionsYield
Stage #1: molsidomine With n-butyllithium In tetrahydrofuran; hexane at -80 - 20℃; for 0.183333h; Inert atmosphere;
Stage #2: 1-methoxy-N,N-dimethylmethanaminium methylsulphate In tetrahydrofuran; hexane; N,N-dimethyl-formamide at 20℃; for 0.333333h; Reagent/catalyst; Inert atmosphere;		66 %Spectr.

Molsidomine Chemical Properties

Structure of Molsidomine (CAS NO.25717-80-0):

IUPAC Name: (1E)-1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate
Molecular Formula: C9H14N4O4
Molar mass: 242.2319 g/mol
Melting Point: 140-141 °C
Storage Temp.: 2-8 °C
XLogP3-AA: 2.2
H-Bond Acceptor: 7
Rotatable Bond Count: 4
Exact Mass: 242.101505
MonoIsotopic Mass: 242.101505
Topological Polar Surface Area: 87
Heavy Atom Count: 17 
Canonical SMILES: CCOC(=NC1=C[N+](=NO1)N2CCOCC2)[O-]
Isomeric SMILES: CCO/C(=N/C1=C[N+](=NO1)N2CCOCC2)/[O-]
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
InChIKey: XLFWDASMENKTKL-UHFFFAOYSA-N
EINECS: 247-207-4
Product Categories: Nitric Oxide

Molsidomine Uses

 Molsidomine (CAS NO.25717-80-0) is an orally active, long acting vasodilating drug. It is metabolized in the liver to the active metabolite SIN-1. Molsidomine is applicable in the treatment of angina pectoris, myocardial infarction (acute phase excluded), chronic conditions such as coronary insufficiency.

Molsidomine Toxicity Data With Reference

1.    

orl-rat LD50:1050 mg/kg

     NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),858.
2.    

ipr-rat LD50:1250 mg/kg

     MEIEDD    Merck Index. 10 (1983),892.
3.    

scu-rat LD50:1360 mg/kg

     MEIEDD    Merck Index. 10 (1983),892.
4.    

ivn-rat LD50:800 mg/kg

     MEIEDD    Merck Index. 10 (1983),892.
5.    

orl-mus LD50:830 mg/kg

     NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),858.

Molsidomine Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 22 
R22:Harmful if swallowed.
Safety Statements: 36 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: WU7677400
Moderately toxic by ingestion, intravenous, intraperitoneal, and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx.

Molsidomine Specification

 Molsidomine (CAS NO.25717-80-0) also can be called BRN 3999414 ; Corvaton ; Covarsal ; Molsidolat ; Molsidomina ; Molsidomina [INN-Spanish] ; Molsidominum ; Molsidominum [INN-Latin] ; Morial ; Morsydomine ; Motazomin ; N-(Ethoxycarbonyl)-3-(4-morpholinyl)sydnone imine ; N-Carboxy-3-morpholinosydnone imine ethyl ester ; N-Carboxy-3-morpholinosydnonimine ethyl ester ; N-Ethoxycarbonyl-3-morpholinosydnonimine ; SIN-10 ; UNII-D46583G77X . Molsidomine (CAS NO.25717-80-0) is colorless or white crystalline powder. It is easily soluble in chloroform, soluble in dilute hydrochloric acid, ethanol, ethyl acetate, insoluble in water, benzene, acetone and extremely difficult soluble in ether.

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