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Dantrolene sodium salt, also known as Dantrium, is an anhydrous sodium salt derived from dantrolene, a compound that acts as an inhibitor of calcium release from the sarcoplasmic reticulum. It possesses the ability to bind to sarcoplasmic reticulum vesicles and reduce the frequency and amplitude of calcium waves, making it a potent skeletal muscle relaxant.

14663-23-1

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14663-23-1 Usage

Uses

Used in Pharmaceutical Industry:
Dantrolene sodium salt is used as a skeletal muscle relaxant for the treatment of malignant hyperthermia, a potentially life-threatening condition characterized by rapid and uncontrolled muscle contractions. It works by inhibiting intracellular Ca2+ release from the sarcoplasmic reticulum, thus reducing the magnitude of electrically stimulated twitch tensions in muscles.
Additionally, Dantrolene sodium salt is used as a blocker of Ca2+ release, which can help in managing muscle spasms and other related conditions by reducing the frequency and amplitude of calcium waves in the presence of calmodulin in isolated cardiomyocytes.

Biological Activity

Inhibits release of Ca 2+ from sarcoplasmic reticulum via inhibition of ryanodine receptor (RYR) channels. Displays selectivity for RYR1 and RYR3 over RYR2. Protective against the effects of a variety of conditions and agents, including excitatory amino acids. Skeletal muscle relaxant and neuroprotectant.

References

1) Zhao?et al.?(2001),?Dantrolene inhibition of ryanodine receptor Ca2+ release channels. Molecular mechanism and isoform selectivity; J. Biol. Chem.,?276?13810 2) Frandsen and Schousboe (1992),?Mobilization of dantrolene-sensitive intracellular calcium pools is involved in the cytotoxicity induced by quisqualate and N-methyl-D-aspartate but not by 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionate and kainite in cultured cerebral cortical neurons; Proc. Natl. Acad. Sci. USA,?89?2590 3) Muehlschlegel and Sims (2009),?Dantrolene: mechanisms of neuroprotection and possible clinical applications in the neurointensive care unit; Neuro. Crit. Care,?10?103 4) Lu?et al.?(2014),?A calcium-dependent protease as a potential therapeutic target for Wolfram syndrome; Proc. Natl. Acad. Sci. USA,?111?E5292

Check Digit Verification of cas no

The CAS Registry Mumber 14663-23-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,6,6 and 3 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 14663-23:
(7*1)+(6*4)+(5*6)+(4*6)+(3*3)+(2*2)+(1*3)=101
101 % 10 = 1
So 14663-23-1 is a valid CAS Registry Number.
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);/b15-7+;

14663-23-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Price
  • Detail

  • TCI America

  • (D3996)  Dantrolene Sodium Salt Hydrate  >98.0%(HPLC)(T)

  • 14663-23-1

  • 1g

  • 690.00CNY

  • Detail

  • TCI America

  • (D3996)  Dantrolene Sodium Salt Hydrate  >98.0%(HPLC)(T)

  • 14663-23-1

  • 5g

  • 2,150.00CNY

  • Detail

  • Sigma

  • (D9175)  Dantrolenesodiumsalt  

  • 14663-23-1

  • D9175-100MG

  • 836.55CNY

  • Detail

  • Sigma

  • (D9175)  Dantrolenesodiumsalt  

  • 14663-23-1

  • D9175-250MG

  • 1,854.45CNY

  • Detail

  • Sigma

  • (D9175)  Dantrolenesodiumsalt  

  • 14663-23-1

  • D9175-1G

  • 5,054.40CNY

  • Detail

14663-23-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name dantrolene sodium (anhydrous)

1.2 Other means of identification

Product number -
Other names 1-[5-(4-Nitrophenyl)furfurylideneamino]hydantoin Sodium Salt Hydrate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14663-23-1 SDS

14663-23-1Synthetic route

dantrolene
7261-97-4

dantrolene

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
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%
5-(4-nitrophenyl)-2-furaldehyde
7147-77-5

5-(4-nitrophenyl)-2-furaldehyde

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
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
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

dantrolene
7261-97-4

dantrolene

Conditions
ConditionsYield
With acetic acid In N,N-dimethyl-formamide at 20℃;98%
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

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

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%
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

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

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%
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

di-tert-butyl chloromethyl phosphate
229625-50-7

di-tert-butyl chloromethyl phosphate

C23H29N4O9P

C23H29N4O9P

Conditions
ConditionsYield
With sodium iodide In N,N-dimethyl-formamide at 0 - 20℃; for 64h; Temperature;45%
N-[(1,1-dimethylethoxy)carbonyl]glycine chloromethyl ester
34573-36-9

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

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C22H23N5O9

C22H23N5O9

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

tert-butyl chloromethyl butanedioate

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C23H24N4O9

C23H24N4O9

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 20h;20%
1-benzyl-4-(2-hydroxyethyl)piperazine
3221-20-3

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

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

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%
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

2-bromoethanol
540-51-2

2-bromoethanol

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

(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;
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 20 °C
2: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C
3: potassium carbonate / N,N-dimethyl-formamide / 20 °C
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C20H21N5O5

C20H21N5O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C21H23N5O5

C21H23N5O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 20 °C
2: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C
3: potassium carbonate / N,N-dimethyl-formamide / 20 °C
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C15H12N4O6

C15H12N4O6

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid / N,N-dimethyl-formamide / 20 °C
2: potassium carbonate / water / 24 h / 20 °C
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C15H11ClN4O5

C15H11ClN4O5

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid / N,N-dimethyl-formamide / 20 °C
2: potassium carbonate / water / 24 h / 20 °C
3: phosphorus trichloride / N,N-dimethyl-formamide; acetone / 2.16 h / 0 - 20 °C
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C21H21N5O8

C21H21N5O8

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid / N,N-dimethyl-formamide / 20 °C
2: potassium carbonate / water / 24 h / 20 °C
3: triethylamine / N,N-dimethyl-formamide / 60 °C
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C21H21N5O8*ClH

C21H21N5O8*ClH

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid / N,N-dimethyl-formamide / 20 °C
2: potassium carbonate / water / 24 h / 20 °C
3: triethylamine / N,N-dimethyl-formamide / 60 °C
4: hydrogenchloride / water; 1,4-dioxane / 2 h / 20 °C
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C29H33N5O8Si

C29H33N5O8Si

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid / N,N-dimethyl-formamide / 20 °C
2: potassium carbonate / water / 24 h / 20 °C
3: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C23H19N5O8

C23H19N5O8

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid / N,N-dimethyl-formamide / 20 °C
2: potassium carbonate / water / 24 h / 20 °C
3: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C
4: toluene-4-sulfonic acid / 1,4-dioxane; methanol / 16 h / 20 °C
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C27H23N5O11

C27H23N5O11

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: acetic acid / N,N-dimethyl-formamide / 20 °C
2: potassium carbonate / water / 24 h / 20 °C
3: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C
4: toluene-4-sulfonic acid / 1,4-dioxane; methanol / 16 h / 20 °C
5: toluene-4-sulfonic acid / 1,4-dioxane; m-xylene / 16 h / Molecular sieve; Reflux
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C27H23N5O11*C4H11NO3

C27H23N5O11*C4H11NO3

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: acetic acid / N,N-dimethyl-formamide / 20 °C
2: potassium carbonate / water / 24 h / 20 °C
3: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C
4: toluene-4-sulfonic acid / 1,4-dioxane; methanol / 16 h / 20 °C
5: toluene-4-sulfonic acid / 1,4-dioxane; m-xylene / 16 h / Molecular sieve; Reflux
6: water / 3 h / 20 °C
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

C15H11N4O9P(2-)*2Na(1+)

C15H11N4O9P(2-)*2Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium iodide / N,N-dimethyl-formamide / 64 h / 0 - 20 °C
2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
2.2: 20 °C / pH 8.5
View Scheme
1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt
14663-23-1

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

dantrolene sodium trihemihydrate

dantrolene sodium trihemihydrate

Conditions
ConditionsYield
With water In methanol at 20 - 30℃; for 6h;

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