Phenytoin-N,C , CAS No.78213-26-0

CAS: 78213-26-0 Cat. No.: P1423736 Summenformel: C₁₄₁₃CH₁₂₁₅N₂O₂ Molekulargewicht: 255.25

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

Phenytoin- 15 N 2 , 13 C is the 13 C and 15 N labeled Phenytoin. Phenytoin (5,5-Diphenylhydantoin) is a potent Voltage-gated Na+ channels (VGSCs) blocker. Phenytoin has antiepileptic activity and reduces breast tumour growth and metastasis in mice.

Specifications

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Namen und Kennungen

Molekulargewicht

255.25

Application Protocols

• No item-specific, validated application protocols are provided in the Product Data.
• General guidance for common research uses (non-validated; adapt to your lab’s SOPs)
  • Stock solutions: Prepare at 10–100 mM in anhydrous DMSO; filter through 0.22 μm PTFE if particulate is present. Store aliquots at −20 °C, protected from light and moisture.
  • LC–MS internal standard: Spike an appropriate concentration (e.g., 10–500 ng/mL, matrix- and method-dependent) into calibration and QC samples; verify recovery, matrix effects, and stability (bench-top, autosampler, freeze–thaw) per your validation plan.
  • Electrophysiology/biochemical assays: Dilute DMSO stocks into buffer or media keeping final DMSO ≤1–2% v/v; include vehicle controls. Confirm compound identity and purity before use.
• Important: The above are general recommendations for phenytoin-like small molecules and do not constitute validated protocols for SKU P1423736.

Biological Roles

• Scope and disclaimer
  • Information below reflects literature on the phenytoin scaffold and is provided for biochemical context only. This product is for research use only and not for human or veterinary applications.
• Mechanistic themes (literature/general)
  • Hydantoin derivatives, including phenytoin, are widely studied as modulators of voltage-gated ion channels, especially Na+ channels, affecting channel inactivation kinetics in cellular electrophysiology models.
  • The aromatic-imide framework contributes to membrane partitioning (logP ~2.5–2.9, literature) and target engagement in ion-channel binding sites.
  • Metabolic fate studies describe aromatic hydroxylation (e.g., p-hydroxylation on phenyl rings) and imide N-glucuronidation as phase I/II pathways (species- and system-dependent; literature).
• Research utilities
  • Isotopically labeled variants (if applicable to this SKU) are valuable as internal standards for quantitative LC–MS of exposure/turnover in microsomes, hepatocytes, or cell lysates, and for tracing biotransformation routes.
• Caution
  • Do not infer any therapeutic utility or dosing from this information. For experimental design, confirm the exact structure and labeling pattern on the CoA/SDS and adhere to institutional biosafety guidelines.

Buffer Applications

• This product is a small, largely non-ionic organic molecule (hydantoin scaffold) and is not used as a buffering agent.
• Practical note
  • If preparing aqueous solutions or assay media, solubilize first in a miscible organic co-solvent (e.g., DMSO or ethanol) before diluting into the buffer. Maintain final organic content at levels compatible with your biological/analytical system (commonly ≤1–2% v/v in biochemical assays).
• For pH-dependent solubility adjustments, mild basification (to deprotonate the imide N–H) can increase aqueous solubility, but strong base may promote side reactions; validate conditions for your application.

Green Alternatives

• Solvent and process optimization offer the most impactful greening for handling phenytoin-type compounds.

• Greener solvent choices (general)

  • Replace DMF/DMAc/NMP where feasible with ethyl acetate, 2-MeTHF, CPME, or MeCN for workups and some reactions.
  • Use water/ethanol cosolvent systems for recrystallization when solubility allows; employ pH adjustment to aid dissolution of the imide anion.

• Comparison (general guidance)

  • Conventional: DMF, DMSO, dichloromethane
  • Greener alternative: 2-MeTHF, CPME, ethyl acetate
  • Trade-offs: DMF/DMSO excel at solubilization but are challenging to remove; 2-MeTHF/CPME are less polar (may require higher temperature/longer time) but have improved EHS profiles.

• Energy and waste reduction

  • Favor high-solids reactions or mechanochemistry for N-alkylations (reported for imides) to cut solvent use.
  • Employ catalytic phase-transfer conditions (e.g., quaternary ammonium salts in biphasic systems) to reduce strong base loadings.

• Analytical greening

  • For LC methods, consider shorter columns, core–shell particles, and higher-temperature operation to lower solvent consumption. Replace acetonitrile with ethanol when method sensitivity allows.

• Note: Selection must still meet reaction/analytical performance. Validate greener substitutions with small-scale trials before scale-up.

Pharmaceutical Uses

• Item-specific status: Not specified for this item; refer to CoA/Spec Sheet.
• Context (general, non-clinical)
  • The phenytoin scaffold is the subject of numerous pharmacopeial and analytical monographs as an active pharmaceutical ingredient; however, SKU P1423736 is supplied strictly for research use only (not for formulation, therapeutic, or diagnostic use).
  • Isotopically labeled or specifically substituted variants (if applicable) are commonly employed as analytical reference standards in pharmaceutical development and quality control to support method validation, matrix effects studies, and mass-balance investigations.
• Formulation-related research considerations
  • Solubility enhancement strategies explored in pre-formulation research include salt formation (via imide deprotonation), co-solvents, cyclodextrin inclusion complexes, and solid dispersions; such findings can guide in vitro research but do not imply suitability of this item for clinical formulation.
• Compliance note
  • No pharmacopeial grade, GMP status, or excipient role is claimed for this item. Consult the CoA for purity and analytical characterization details if using as a research standard.

Physical Properties

• Item-specific properties
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Storage and shipping (from Product Data)
  • Storage: Store at −20 °C.
  • Shipping: Ice chest + ice pads.
• Safety-relevant handling property
  • Hygroscopicity/oxidation/peroxide-forming tendency: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/general values for the phenytoin scaffold (for orientation only; exact values for this SKU may differ if modified or isotopically labeled)
  • Molecular formula (phenytoin): C15H12N2O2 (literature)
  • Molecular weight (phenytoin): 252.27 g/mol (literature)
  • Melting point: ~295–298 °C, with decomposition (literature)
  • LogP (octanol/water): ~2.5–2.9 (literature; method-dependent)
  • pKa (imide N–H): ~8.3–8.5 (literature; aqueous, ionic strength dependent)
  • Solubility: sparingly soluble in water; soluble in polar organic solvents such as DMSO, DMF, ethanol, acetone (literature)
  • UV characteristics: intense aromatic absorption ~200–230 nm with weaker bands near 250–270 nm (literature; solvent-dependent)
• Critical note
  • Do not treat literature values as specifications for SKU P1423736. When preparing solutions or calibrations, confirm the exact identity and relevant physico-chemical data on the item’s CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• What to look for on the CoA/Spec Sheet for phenytoin-type materials
  • Identity confirmation: 1H/13C NMR, HRMS (pay attention to isotopic patterns if N/C labeling is intended), IR, and HPLC/UPLC purity. For isotopologues, atom% enrichment and labeling positions should be explicitly stated.
  • Purity metrics: area% by HPLC/UPLC, residual solvent content (GC), water by Karl Fischer, and limit tests for related substances. If the product is intended for LC–MS workflows, low non-volatile residues are advantageous.
  • Optical data: UV profile and extinction coefficients can assist in analytical method development; for labeled variants, these generally mirror the unlabeled chromophore.
• Grade context (general)
  • Research grade indicates suitability for laboratory research, method development, and screening; not for human or veterinary use.
  • If an “analytical standard” or “LC–MS grade” is stated on the CoA, expect tighter control of purity, counter-ions (if a salt), and documented stability.
• Stabilizers/additives
  • Not specified for this item; refer to CoA/Spec Sheet. If present, stabilizers should be disclosed and considered when preparing quantitative standards.

Reaction and Applications

• Research applications (general for phenytoin-type compounds)
  • Analytical: reference material or internal standard in metabolism, toxicology, and forensic method development (research use only).
  • Probe chemistry: hydantoin scaffold used in ion-channel pharmacology and SAR exploration; isotopic labels (if present) support tracer and mass-balance studies.
• Transformations on the hydantoin core (literature/general)
  • N-Functionalization: the imide N–H can be deprotonated (e.g., NaH, K2CO3/Cs2CO3) and alkylated or acylated to tune lipophilicity and binding.
  • Ring functionalization: electrophilic aromatic substitution on the phenyl rings (nitration, halogenation, sulfonylation) for late-stage diversification.
  • Hydrolysis/opening: strong basic or enzymatic conditions can open the imide ring to diamide/ureide derivatives; typically avoided unless targeted.
  • Metal complexation: the imide can weakly coordinate metals; derivatization to stronger chelating motifs is more common for labeling.
• Practical tips
  • Dry conditions: use anhydrous solvents and inert gas for base-mediated N-alkylations to minimize hydrolysis.
  • Monitoring: HPLC/UPLC with UV at 210–220 nm or 254–270 nm tracks progress; LC–MS provides unambiguous mass changes, useful for labeled variants.
  • Workup: quench bases carefully; partition between EtOAc and mildly acidic aqueous phases to recover the neutral imide.
• Item-specific manufacturer applications
  • Not provided in Product Data. If employing this SKU as a labeled standard or SAR intermediate, consult the CoA for exact labeling pattern and enrichment to design experiments appropriately.

Reaction Conditions

• General conditions for common transformations on hydantoin (literature guidance; adjust to your substrate and scale)
  • N-Alkylation: NaH (1.1–1.5 equiv) in dry DMF or THF at 0–25 °C, then add alkyl halide (1.1–1.5 equiv); typical reaction times 1–4 h. Work up by careful quench with MeOH/H2O, extract with EtOAc. Yields often 60–90% depending on sterics and base.
  • N-Acylation/Sulfonylation: K2CO3/Cs2CO3 (2–3 equiv) in MeCN or acetone with acyl/sulfonyl chloride (1.1–1.5 equiv), 20–50 °C, 2–8 h; include catalytic DMAP for acylations as needed.
  • Aromatic substitution: Electrophilic halogenation (e.g., NBS, NCS) on activated positions under controlled conditions; cross-coupling requires prefunctionalized aryl substrates (Pd-catalyzed Suzuki/Heck typical conditions, 60–120 °C in dioxane/EtOH/H2O).
  • Hydrolysis (if desired): Aqueous NaOH or KOH (1–3 M), reflux to open the imide; neutralize to isolate diamide/ureide products. Use caution to avoid over-degradation.
• Analytics and control
  • LC–MS with ESI provides clear mass tracking; UV detection at 210–220 or ~254–270 nm suitable for aromatic hydantoins.
  • For labeled materials, verify isotopic integrity by HRMS and, where applicable, 13C/15N NMR.
• Notes
  • Parameters above are representative literature guidance and not specifications for SKU P1423736. Optimize for your substrate. If this item is an isotopologue, minimize protic/base-catalyzed exchange that could scramble labels.

Safety and Handling

• Authoritative source: Always consult the product SDS for definitive hazard, first-aid, and disposal guidance.
• Item-specific hazard data (from Product Data)
  • Signal word: Not specified for this item; refer to SDS.
  • H-statements: Not specified for this item; refer to SDS.
  • GHS classification/pictograms: Not specified for this item; refer to SDS.
• General laboratory precautions for small organic solids (applicable to phenytoin-type compounds)
  • PPE: lab coat, nitrile gloves, safety glasses; use a certified fume hood to avoid dust inhalation.
  • Avoid generating dust/aerosols; employ local exhaust ventilation when weighing or transferring powders.
  • Incompatibilities: strong oxidizers and strong bases/acids may promote degradation or undesired reactions of imide functionality (general guidance).
  • Thermal stability: hydantoin derivatives often decompose upon strong heating; avoid temperatures near decomposition.
• First-aid overview (general)
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; obtain medical advice if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting unless directed by medical personnel; seek medical attention.
• Spill and disposal (general)
  • Avoid dust; dampen and collect with inert absorbent, place in sealed container for disposal per local regulations.
  • Waste handling: treat as organic laboratory chemical waste; follow institutional and regulatory requirements.
• Transportation/storage
  • Store at −20 °C in a tightly closed container, protected from light and moisture per Product Data.
  • Ship and unpack with cold packs; equilibrate in a desiccator if condensation is possible.

Solvent Selection

• Intended use context
  • As a hydantoin-based, aromatic small molecule, phenytoin-like compounds typically show low aqueous solubility but dissolve in polar aprotic and certain protic organic solvents.
• Practical solvent guidance (literature/general for the phenytoin scaffold)
  • High solubility: DMSO, DMF, NMP; suitable for stock solutions for bioassays and analytics.
  • Moderate solubility: ethanol, methanol, acetone, acetonitrile, ethyl acetate.
  • Low solubility: water and non-polar alkanes.
  • pH leverage: deprotonation of the imide N–H (pKa ~8.3–8.5, literature) increases aqueous solubility; avoid strong base if N-alkylation or hydrolysis is a concern.
• Selection tips
  • For LC–MS: use acetonitrile/water with 0.1% formic acid or ammonium formate; dissolve first in a small volume of DMSO or MeOH if needed, then dilute.
  • For N-alkylation chemistry: dry polar aprotics (DMF, DMSO) with non-nucleophilic base (NaH, Cs2CO3); inert atmosphere recommended.
  • For crystallization: ethanol/acetone or EtOAc/hexane systems can be tuned for slow crystallization of hydantoin derivatives.
• Comparison snapshot (general)
  • DMSO vs DMF: DMSO offers superior solubilization and is more benign toward glassware; DMF can be easier to remove but is more moisture sensitive in base-promoted reactions.
  • Alcohols vs acetonitrile: alcohols aid in proton transfers; acetonitrile is preferred for analytical compatibility.
• Note: Verify the exact form (free base/imide, salt, or labeled derivative) on the CoA, as salts or isotopic substitutions can subtly affect solubility.

Storage and Reconstitution

• Storage conditions (from Product Data)
  • Store at −20 °C in a tightly sealed container.
  • Shipped in an ice chest with ice pads; upon receipt, place immediately into −20 °C storage.
• Stability considerations
  • Protect from moisture and prolonged exposure to light and elevated temperatures. Allow vials to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation.
  • For isotopically labeled materials (if applicable), avoid strong basic or protic conditions that could promote label exchange or hydrolysis.
• Reconstitution and solution handling (general guidance)
  • Preferred solvents for stock: anhydrous DMSO or DMF. Typical research stocks: 10–100 mM depending on solubility.
  • For aqueous use, pre-dissolve in a small volume of organic solvent, then dilute into buffer. Adjust pH only as needed; excessive base may cause side reactions.
  • Filter sterilize solutions intended for cell-based assays with 0.22 μm PTFE or PES filters.
• Aliquoting and shelf life
  • Prepare single-use aliquots to minimize freeze–thaw. Store solutions at −20 °C (DMSO) or 2–8 °C (short-term) and verify stability by LC–MS/UPLC before critical experiments.
• Item-specific notes (if any)
  • Appearance, purity, and exact solubility: Not specified for this item; refer to CoA/Spec Sheet.
  • Always consult the SDS for additional handling and storage precautions.

Structure and Identity

• Item-specific identifiers
  • CAS: 78213-26-0 (per Product Data)
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• Naming note
  • The name “Phenytoin-N,C” suggests a phenytoin scaffold with N/C-specific modification (often used to denote positional or isotopic labeling). The exact substitution/labeling pattern for this SKU is not specified; consult the CoA/Spec Sheet for definitive structure.
• Structural context (literature/general chemistry, for the phenytoin scaffold)
  • Core scaffold: hydantoin (imidazolidine-2,4-dione) bearing two phenyl groups at C-5 (5,5-diphenylhydantoin).
  • Functional groups: cyclic imide (two carbonyls), one imide N–H (acidic), and two pendant phenyl rings.
  • 2D description: a five-membered imidazolidinedione ring (two carbonyls at C2 and C4), with both substituents at C5 being phenyl groups; one ring nitrogen is proton-bearing.
• Stereochemistry: phenytoin itself is achiral (meso-like substitution at C5). If N/C labeling or substitution is present, chirality remains unlikely unless asymmetry is introduced by substitution (not specified for this item).
• Please verify the exact identity (including any isotopic enrichment sites and atom% labeling, if applicable) on the product’s CoA prior to use in analytical or mechanistic studies.

Synthetic Utility

• Functional handles on the phenytoin core (literature/general)
  • Imide N–H (acidic): platform for N-alkylation, N-acylation, and sulfonylation to modulate physicochemical properties.
  • Aromatic rings: amenable to electrophilic substitution (e.g., halogenation, nitration) and cross-coupling after prefunctionalization (e.g., convert to aryl halides via directed methods on suitably substituted analogs).
  • Carbonyls: reduction or condensation is less common due to ring stability but can be leveraged in specialized transformations or ring-opening strategies.
• Retrosynthetic value
  • Hydantoin derivatives connect ureas and amino acid–like building blocks; ring closure strategies (Biltz/Bucherer–Bergs chemistry) enable scaffold diversification and isotope incorporation at N/C positions in synthetic planning.
• Applications
  • Synthesis of labeled internal standards: introduce 13C/15N at the imide carbonyls or ring nitrogens through labeled urea/CO2 precursors (general strategy; confirm labeling sites for this SKU on CoA).
  • Late-stage functionalization of the phenyl rings allows SAR series expansion while maintaining the hydantoin pharmacophore.
• Practical considerations
  • Employ strong, non-nucleophilic bases (NaH, KHMDS) for clean N-alkylation in dry polar aprotic solvents.
  • Monitor by LC–MS; isotopic labeling facilitates confirmation through exact mass shifts and isotopic patterns.
  • Protect the imide from hydrolysis under prolonged basic aqueous conditions.

Target Specificity

• Not applicable. This product is a small molecule, not an antibody or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity information applies.
• For biochemical studies, any discussion of protein targets (e.g., ion channels) is exploratory and literature-based; this SKU’s exact target interactions are not specified in the Product Data.