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DESCRIPTION
DM Hydantoin refers to a compound used in various industries, including pharmaceuticals and cosmetics.
It is derived from hydantoin, which is a heterocyclic organic compound containing both nitrogen and oxygen atoms.
Hydantoin derivatives, like DM Hydantoin, are commonly employed as intermediates in the synthesis of medications or as preservatives in personal care products.
Cas Number: 160-70-7
SYNONYMS
6440-58-0,1,3-Bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione,DMDM Hydantoin,Dimethyloldimethyl hydantoin,Glydant,Dmdmh,1,3-Bis(hydroxymethyl)-5,5-dimethylhydantoin,1,3-Dimethylol-5,5-dimethylhydantoin,Dantoin-DMDMH,Glycoserve-DMDMH,Dantoin dmdmh 55,Dimethylol-5,5-dimethylhydantoin,Dmdmh 55,Caswell No. 273AB,2,4-Imidazolidinedione, 1,3-bis(hydroxymethyl)-5,5-dimethyl-,dimethyloldimethylhydantoin,UNII-BYR0546TOW,EINECS 229-222-8,BYR0546TOW,EPA Pesticide Chemical Code 115501,1,3-Bis(hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedione,BRN 0882348,DTXSID8035217,HSDB 7488,1,3-Di(hydroxymethyl)-5,5-dimethylhydantoin,MFCD00467199,DTXCID6015217,1,3-DIMETHYLOL-5,5-DIMETHYL-HYDANTOIN,EC 229-222-8,Hydantoin, 1,3-bis(hydroxymethyl)-5,5-dimethyl-,DMDM HYDANTOIN (II),DMDM HYDANTOIN [II],Dantoguard,1,3-DIHYDROXYMETHYL-5,5-DIMETHYLHYDANTOIN,Dantion DMDMH 55,DMDM HYDANTION,1,3-Dihydroxylmethyl-5,5-dimethylhydantoin,SCHEMBL69185,DMDM HYDANTION [VANDF],DMDM HYDANTOIN [VANDF],DDAC0.6%,DDAC0.15%,Tox21_303842,AKOS006345746,n,n'-dimethylol-5,5-dimethylhydantoin,CS-W021276,USEPA/OPP Pesticide Code: 115501,NCGC00356947-01,AS-10924,SY101650,CAS-6440-58-0,NS00007210,H11751,Q5205613,W-104844,1,3-DIMETHYLOL-5,5-DIMETHYLHYDANTOIN [HSDB],1,3-Bis (hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione,1,3,BIS(HYDROXYMETHYL)-5,5-,DIMETHYLHYDANTOINDIMETHYLHYDANTOIN,1,3 BIS(HYDROXYMETHYL)-5,5,DIMETHYLHYDANTOINDIMETHYLHYDANTOIN,1 pound not3-Bis(hydroxymethyl)-5 pound not5,dimethylimidazolidine-2 pound not4-dione
In a pharmaceutical context, DM Hydantoin can be involved in producing anticonvulsants or used in medicinal chemistry for developing drugs targeting neurological conditions.
In cosmetics, it might be used as a stabilizing agent or preservative in formulations.
Definition and Chemical Structure of DM Hydantoin:
DM Hydantoin, or Dimethylhydantoin, is a derivative of hydantoin, a five-membered heterocyclic compound.
It has the molecular formula C5H8N2O2, and the key structural feature includes two methyl groups (-CH3) attached to nitrogen atoms in the hydantoin ring.
This modification alters the chemical properties of the molecule, enhancing its utility in pharmaceutical and industrial applications.
The molecule can be represented as:
C5H8N2O2C5H8N2O2
Overview of its Synthesis and Early Discovery:
Hydantoins were first synthesized in the 19th century, with DM Hydantoin emerging as a more modern derivative due to its enhanced properties.
Early research focused on improving the stability and bioavailability of hydantoin compounds, and DM Hydantoin was identified as a compound with potential therapeutic properties.
Importance and Uses in Pharmaceutical and Industrial Applications:
DM Hydantoin is widely used in the pharmaceutical industry as an anticonvulsant agent.
Additionally, it has applications in the production of various polymers, resins, and coatings, thanks to its stability and chemical versatility.
Chemical Properties of DM Hydantoin
Molecular Formula, Molecular Weight, and Key Chemical Properties:
DM Hydantoin’s molecular weight is approximately 128.13 g/mol.
The compound is relatively stable under standard conditions, though it can decompose under extreme conditions of heat or in the presence of strong acids or bases.
It exhibits weak basicity due to the nitrogen atoms in its heterocyclic ring structure.
Solubility, Stability, and Reactivity:
DM Hydantoin is moderately soluble in water and organic solvents like ethanol and acetone.
Its stability is maintained in neutral to slightly acidic conditions but can be affected by exposure to strong acids or alkalis.
In terms of reactivity, it undergoes typical nucleophilic substitution reactions due to the presence of nitrogen atoms, which can serve as electrophilic sites.
Comparison with Other Hydantoin Derivatives:
Compared to other hydantoin derivatives, DM Hydantoin has a higher degree of lipophilicity due to the methyl groups, which enhance its penetration across lipid membranes.
This property makes it more effective in biological systems.
Synthesis and Manufacturing
Synthetic Pathways for DM Hydantoin:
DM Hydantoin can be synthesized from hydantoin itself via alkylation reactions, in which methylating agents like dimethyl sulfate (DMS) or methyl iodide (CH3I) react with hydantoin under basic conditions.
The process involves the introduction of two methyl groups into the hydantoin ring structure, resulting in DM Hydantoin.
Chemical Reactions Involved in its Production:
The synthesis typically begins with the deprotonation of hydantoin, followed by nucleophilic substitution where the methyl group from the methylating agent attaches to one of the nitrogen atoms in the ring.
The process is typically performed in the presence of a base like sodium hydroxide (NaOH).
Industrial Methods and Scale-up Processes:
In industrial-scale manufacturing, the reaction is carried out under controlled conditions of temperature and pressure to optimize yield.
Solvent extraction is used to purify the product, and recrystallization may be used to further purify the DM Hydantoin.
Mechanisms of Action
Pharmacodynamics of DM Hydantoin:
DM Hydantoin acts primarily as an anticonvulsant by inhibiting the activity of sodium channels in neurons.
This inhibition reduces the ability of neurons to fire action potentials, thereby controlling abnormal electrical activity in the brain.
Additionally, it may have sedative properties by modulating GABAergic (gamma-aminobutyric acid) systems.
How it Interacts with Biological Systems:
DM Hydantoin interacts with ion channels and enzymes involved in neurotransmission.
Its binding to sodium channels helps stabilize cell membranes, preventing the hyperexcitability that can lead to seizures.
Enzyme Inhibition and Receptor Interactions:
Apart from sodium channel blockade, DM Hydantoin may have mild interactions with enzymes like cytochrome P450, affecting its own metabolism and the metabolism of co-administered drugs.
Biological Effects and Therapeutic Applications
Specific Medical Conditions Treated with DM Hydantoin:
DM Hydantoin is most commonly used for treating generalized tonic-clonic seizures and partial seizures in epilepsy.
It has also been investigated in the treatment of anxiety disorders, although its use for this purpose is less widespread.
Mechanisms Behind Its Therapeutic Effects:
As discussed earlier, DM Hydantoin’s anticonvulsant effect is largely due to its ability to inhibit sodium channels and stabilize neuronal membranes.
The sedative effects are believed to be mediated through GABAergic mechanisms, though this is less well-established.
Case Studies and Clinical Trials:
Studies have shown that DM Hydantoin can be effective in managing seizures, particularly when other anticonvulsant drugs fail.
However, its use is less common in modern clinical practice due to the availability of newer drugs with fewer side effects.
Environmental Impact and Industrial Use
Role in Industrial Applications:
DM Hydantoin is used in the production of polymers, resins, and coatings due to its chemical stability and ability to enhance the properties of materials.
It can also act as a crosslinking agent in certain formulations.
Environmental Safety and Biodegradation:
The environmental impact of DM Hydantoin is relatively low, but concerns arise in the context of industrial waste.
Studies suggest that while DM Hydantoin is not highly toxic to aquatic life, its slow degradation in the environment warrants caution.
Regulatory Standards for Industrial Use:
In industrial applications, DM Hydantoin is subject to various safety and environmental regulations.
For instance, handling and disposal procedures must be in accordance with guidelines to minimize exposure and contamination.
Research and Advances in DM Hydantoin
Ongoing Studies and Novel Research Directions:
Research is ongoing into the potential use of DM Hydantoin in treating new indications, such as chronic pain and psychiatric disorders.
Novel formulations that reduce side effects and improve bioavailability are also being investigated.
Future Potential Uses in Medicine, Materials Science, and Biotechnology:
DM Hydantoin may have applications in targeted drug delivery systems, as its ability to cross biological membranes could make it useful in advanced pharmaceutical delivery techniques.
Cutting-Edge Formulations and Analogs:
New analogs of DM Hydantoin are being developed to enhance selectivity for specific sodium channels, thereby reducing off-target effects and improving therapeutic efficacy.
Conclusion
Summary of DM Hydantoin’s Importance and Versatility:
DM Hydantoin is a versatile compound with significant potential in both medical and industrial fields.
While its clinical use has been somewhat overshadowed by newer anticonvulsants, it remains an important part of the pharmacological toolkit for treating certain seizure disorders.
Final Thoughts on Its Future in Research and Applications:
The future of DM Hydantoin may lie in its refined application in niche medical conditions, as well as in its continued use in industrial applications.
Ongoing research will likely unveil new possibilities for its use, both in therapeutic contexts and in advanced materials.
SAFETY INFORMATION ABOUT DMDM HYDANTOIN (DMDMH)
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
