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Dantrolene sodium salt

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Name

Dantrolene sodium salt

EINECS 238-706-8
CAS No. 14663-23-1 Density N/A
PSA 127.05000 LogP 1.71410
Solubility N/A Melting Point N/A
Formula C14H9N4O5Na Boiling Point 85°C 4mm
Molecular Weight 336.239 Flash Point 283.1oC
Transport Information N/A Appearance COA
Safety 22-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 14663-23-1 (Dantrolene sodium salt) Hazard Symbols N/A
Synonyms

2,4-Imidazolidinedione,1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-, sodium salt (9CI);Hydantoin, 1-[[5-(p-nitrophenyl)furfurylidene]amino]-, sodium salt (8CI);Dantrium;Dantrolene sodium;F 440;Sodium dantrolene;

Article Data 1

Dantrolene sodium salt Synthetic route

7261-97-4

dantrolene

14663-23-1

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 3h;100%
7147-77-5

5-(4-nitrophenyl)-2-furaldehyde

14663-23-1

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 81 percent / H2O; dimethylformamide
2: 100 percent / CH3ONa / methanol / 3 h / 20 °C
View Scheme
14663-23-1

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt

7261-97-4

dantrolene

Conditions
ConditionsYield
With acetic acid In N,N-dimethyl-formamide at 20℃;98%
14663-23-1

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt

89151-46-2

tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

3-{[(1-tert-butoxycarbonyl)piperidin-4-yl]ethyl}-1-{[5-(4-nitrophenyl)furfurylidene]amino}imidazolidine-2,4-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;96.4%
14663-23-1

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt

145508-94-7

tert-butyl 4-(iodomethyl)piperidine-1-carboxylate

3-{[(1-tert-butoxycarbonyl)piperidin-4-yl]methyl}-1-{[5-(4-nitrophenyl)furfurylidene]amino}imidazolidine-2,4-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;51.6%
14663-23-1

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt

229625-50-7

di-tert-butyl chloromethyl phosphate

C23H29N4O9P

Conditions
ConditionsYield
With sodium iodide In N,N-dimethyl-formamide at 0 - 20℃; for 64h; Temperature;45%
34573-36-9

N-[(1,1-dimethylethoxy)carbonyl]glycine chloromethyl ester

14663-23-1

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt

C22H23N5O9

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 110h;27%
432037-43-9

tert-butyl chloromethyl butanedioate

14663-23-1

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt

C23H24N4O9

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 20h;20%
3221-20-3

1-benzyl-4-(2-hydroxyethyl)piperazine

14663-23-1

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt

3-[(4-benzylpiperizin-1-yl)ethyl]-1-{[5-(4-nitrophenyl)furfurylidene]amino}imidazolidine-2,4-dione

Conditions
ConditionsYield
Stage #1: 1-benzyl-4-(2-hydroxyethyl)piperazine With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 0.333333h; Mitsunobu Displacement;
Stage #2: 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt In tetrahydrofuran at 60℃;
5.7%
14663-23-1

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt

540-51-2

2-bromoethanol

(2-(2-hydroxyethoxy)-1-(((5-(4-nitrophenyl)furan-2-yl)methylene)amino)-1,5-dihydro-4H-imidazole-4-one)

Conditions
ConditionsYield
Stage #1: 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt With potassium carbonate In tetrahydrofuran; water for 0.5h;
Stage #2: 2-bromoethanol In tetrahydrofuran; water at 20℃; for 24h;

Dantrolene sodium salt Chemical Properties

Molecular Structure of Dantrolene sodium salt (CAS NO.14663-23-1):

IUPAC Name: Sodium  3-[(E)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]-5-oxo-4H-imidazol-2-olate
Molecular Formula: C14H9N4O5Na
Molecular Weight: 336.26g/mol
EINECS: 238-706-8
Boiling Point: 544.5 °C at 760 mmHg
Flash Point: 283.1 °C
Properties: solid
 Freely Rotating Bonds: 4 
Polar Surface Area: 124.22 Å2 
Polarizability: 10-24 cm3 
Enthalpy of Vaporization: 86.63 kJ/mol  
Vapour Pressure: 1.09E-12 mmHg at 25°C  
InChI
InChI=1/C14H10N4O5.Na/c19-13-8-17(14(20)16-13)15-7-11-5-6-12(23-11)9-1-3-10(4-2-9)18(21)22;/h1-7H,8H2,(H,16,19,20);/q;+1/p-1/b15-7+;
Smiles
N1(CC([NH-]C1=O)=O)\N=C\c1oc(cc1)c1ccc(cc1)[N+](=O)[O-].[Na+]
The chemical synonyms of Dantrolene sodium salt (CAS NO.14663-23-1) are Sodium dantrolene ; Dantrium ; Dantrolene na ; Dantrolene sodium salt ; 1-[[[5-(4-Nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolinedione sodium salt ; 1-[[[5-(4-Nitrophenyl)-2-furanyl]-methylene]imino]2,4-imidazolidinedione sodium salt ; 1-[(5-[p-Nitrophenyl]furfurylidene)-amino]hydantoin sodium salt ; 1-((5-(p-Nitrophenyl)furfurylidene)amino)hydantoinsodium .
Product categories: Pharmacetical ; API's ; InsP3/Ryanodine receptor .The molecular structure of Dantrium

Dantrolene sodium salt Toxicity Data With Reference

1.    

orl-hmn TDLo:320 mg/kg:BAH,GIT

    JAMAAP    JAMA, Journal of the American Medical Association. 231 (1975),662.
2.    

orl-wmn LDLo:600 mg/kg:GIT,SYS

    NYSJAM    New York State Journal of Medicine. 77 (1977),1759.
3.    

orl-rat LD50:7431 mg/kg

    IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 12 (1981),668.
4.    

ipr-rat LD50:413 mg/kg

    IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 12 (1981),668.
5.    

orl-mus LD50:1188 mg/kg

    JPMSAE    Journal of Pharmaceutical Sciences. 69 (1980),327.
6.    

ipr-mus LD50:534 mg/kg

    IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 12 (1981),668.

Dantrolene sodium salt Safety Profile

Moderately toxic by intraperitoneal and ingestion routes. Human systemic effects by ingestion: anorexia (human), hepatitis, nausea or vomiting, somnolence. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx and Na2O.
Safety Statements: 22-24/25
22:  Do not breathe dust 
24/25:  Avoid contact with skin and eyes
WGK Germany: 2
RTECS: MU3875000

Dantrolene sodium salt Specification

  In order to capture and identify key molecules that regulate the release of Ca(2+) from the sarcoplasmic reticulum (SR) of skeletal muscle, we designed specific photoaffinity probes based on the structural modification of dantrolene. Thus, GIF-0082 and GIF-0276 possessing azido- and trifluoromethyldiazirinyl-benzyl groups, respectively, at the hydantoin moiety were found to have a highly selective inhibitory effect on physiological Ca(2+) release without affecting Ca(2+)-induced Ca(2+) release (CICR). Successful realization of the sharp discrimination between PCR and CICR has led to the creation of [(125)I]GIF-0082 and [(125)I]GIF-0276, which were synthesized by substituting a stannyl group with (125)I in the corresponding phenylstannane precursors. It is a muscle relaxation drug for treatment of diseases associated with spastic paralysis.

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