7261-97-4

Basic information

• Product Name: Dantrolene
• Synonyms: DANTRILENE;1-{(5-(4-NITROPHENYL)-2-FURANYL)METHYLENE}AMINO-2,4-IMIDAZOLIDENEDIONE;1-[[[5-(4-Nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidinedione;1-[5-(4-Nitrophenyl)-2-furylmethyleneamino]imidazolidine-2,4-dione;C06939;Dantrolene (200 mg)
• CAS NO: 7261-97-4
• Molecular Formula: C₁₄H₁₀N₄O₅
• Molecular Weight: 314.256
• EINECS: 230-684-8
• Mol File: 7261-97-4.mol

Chemical Properties

• Melting Point: 279-280°
• Boiling Point: 453.94°C (rough estimate)
• Appearance: /
• Density: 1.3452 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• PKA: 7.68±0.10(Predicted)
• CAS DataBase Reference: Dantrolene(CAS DataBase Reference)
• NIST Chemistry Reference: Dantrolene(7261-97-4)
• EPA Substance Registry System: Dantrolene(7261-97-4)

Safety Data

• Hazardous Substances Data: 7261-97-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Dantrolene is used as a muscle relaxant for the treatment of spasticity and muscle stiffness associated with various conditions such as multiple sclerosis, cerebral palsy, and spinal cord injuries. Its mechanism of action involves the inhibition of Ca2+ release through ryanodine receptor channels, leading to a reduction in muscle contractions and spasticity.

Therapeutic Function

Muscle relaxant

Air & Water Reactions

Slightly water soluble. Dantrolene may be sensitive to heat and air .

Health Hazard

SYMPTOMS: When ingested, symptoms of exposure may include drowsiness, dizziness, weakness, general malaise, fatigue, diarrhea, constipation, gastrointestinal bleeding, anorexia, abdominal cramps, hepatitis, speech disturbance, seizure, headache, light-headedness, insomnia, tachycardia, phlebitis, mental depression, mental confusion, nervousness, abdominal hair growth, rash, sweating, backache, chills and fever.

Fire Hazard

Flash point data for Dantrolene are not available. Dantrolene is probably combustible.

InChI:InChI=1/C14H10N4O5/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+

Upstream product

• 7147-77-5 5-(4-nitrophenyl)-2-furaldehyde 
• 2827-56-7 1-aminohydantoin hydrochloride 
• 98-01-1 furfural 
• 586-78-7 para-nitrophenyl bromide 
• 14663-23-1 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt 
• 100-00-5 4-chlorobenzonitrile 
• 6301-02-6 1-aminohydantoin 

Downstream Products

• 14663-23-1 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt 
• 62452-00-0 3-<3-(N-tert-butoxycarbonylamino)-1-oxopropyl-1-<<5-(4-nitrophenyl)-2-furanyl>methylene>amino>-2,4-imidazolidinedione 

Relevant articles and documents

Mechanochemical Preparation of Protein : hydantoin Hybrids and Their Release Properties

Mechanochemistry is a versatile methodology that can be employed both for covalent bond formation in organic synthesis as well as a mediator to allow preparation novel colloidal dispersions for drug delivery. Herein, ball-milling was employed for the solid-state preparation of fluorescent hydrophobic hydantoins, followed by the unprecedented mechanochemically-mediated complexation of hydrophobic hydantoins within hydrophilic protein β-lactoglobulin (BLG) and BLG nanofibrils (BLGNFs). These hydantoin:protein materials were in turn incorporated into hydrogels. The effect of incorporation of hydantoins into proteins, as well as the effect of protein structure, on the release properties were then investigated. The conversion of BLG to BLGNFs led to a more sustained release demonstrating that heat treatment of BLG into BLGNFs could be employed to modify release properties. To the best of our knowledge, this is the first example where protein : hydantoin complexes were prepared by mechanochemical methodology and mechanochemistry was combined with self-assembly in order to prepare protein nanomaterials for drug-delivery applications. In addition, the use of the developed protein materials is not limited to delivery of drugs but can for example be employed as components of smart food (delivery of nutrients) or release systems of pesticides.

Direct (Hetero)arylation of Heteroarenes Catalyzed by Unsymmetrical Pd-PEPPSI-NHC Complexes under Mild Conditions

With the aim of developing a facile and efficient method to access structurally intriguing and valuable functionalized (hetero)aryls, two unsymmetrical Pd-PEPPSI-type NHC complexes (PEPPSI, pyridine-enhanced precatalyst preparation, stabilization, and initiation; NHC, N-heterocyclic carbene) were designed and synthesized to catalyze the direct arylation of heteroarenes with (hetero)aryl bromides. The results demonstrated that the utilization of this "unsymmetrical"strategy led to much higher efficiency in comparison to the commonly used C2-symmetric Pd-PEPPSI-type NHC complexes. Furthermore, a broad range of heteroaromatics and (hetero)aryl bromide partners with a wide variety of functional groups were all amenable to the developed protocol even at as low as 0.05 mol % catalyst loading and under aerobic conditions. More importantly, along with our study, we also found that the present protocol could provide expedient access to the gram-scale synthesis of the muscle relaxant drug dantrolene and conjugated mesopolymers.

Dantrolene prodrug and method for using same

The disclosure is directed to a dantrolene prodrug, a composition thereof, and a method of using the dantrolene prodrug in the treatment of disease.

Continuous Visible-Light Photoflow Approach for a Manganese-Catalyzed (Het)Arene C?H Arylation

Manganese photocatalysts enabled versatile room-temperature C?H arylation reactions by means of continuous visible-light photoflow, thus allowing for efficient C?H arylations in 30 minutes with ample scope. The robustness of the manganese-catalyzed photoflow strategy was shown by visible light-induced gram-scale synthesis, clearly outperforming the batch performance.

Blue light mediated C-H arylation of heteroarenes using TiO2 as an immobilized photocatalyst in a continuous-flow microreactor

Titanium dioxide was applied as an immobilized photocatalyst in a microstructured falling film reactor for the continuous-flow C-H arylation of heteroarenes with aryldiazonium salts as the starting material. Detailed investigations of the catalyst and a successful long-term run proved its excellent usability for this process. Very good yields up to 99% were achieved with broad substrate scope and were compared with batch synthesis. The transfer to the continuous-flow mode revealed an impressive boost in reactor performance solely resulting from the improved irradiation and contact of the catalyst, substrate and light.

Direct C–H Arylation of Heteroarenes with Aryl Chlorides by Using an Abnormal N-Heterocyclic-Carbene–Palladium Catalyst

Herein, we report a versatile catalytic system for the direct C–H arylation of heteroarenes with activated aryl chloride substrates. The catalyst works successfully for a variety of heteroarenes and aryl chloride coupling partners under very low catalyst-loading conditions. We have successfully performed the direct C–H arylations of 1-methylpyrrole, 1-methylindole, furan, thiophene, furfural, and N-benzyl-1,2,3-triazole with aryl chloride partners in good yields without the use of any additives. Furthermore, we used this catalytic process to develop a one-pot synthetic protocol for the muscle relaxant dantrolene on a gram scale. Additionally, the present catalytic system can be used to perform consecutive arylations in one pot.

Ascorbic acid as an initiator for the direct C-H arylation of (hetero)arenes with anilines nitrosated in situ

Ascorbic acid (vitaminC) has been used as a radical initiator in a metal-free direct C-H arylation of (hetero)arenes. Starting from an aniline, the corresponding arenediazonium ion is generated in situ and immediately reduced by vitaminC to an aryl radical that undergoes a homolytic aromatic substitution with a (hetero)arene. Notably, neither heating nor irradiation is required. This procedure is mild, operationally simple, and constitutes a greener approach to arylation. Copyright