Triamterene-d5 - ≥99% , CAS No.1189922-23-3

CAS: 1189922-23-3 Cat. No.: T651384 Summenformel: C₁₂H₆D₅N₇ Molekulargewicht: 258.29

GRADE & PURITY ≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

Triamterene-d 5 is deuterium labeled Triamterene, which can block epithelial Na+ channel (ENaC) in a voltage-dependent manner, which used as a mild diuretic.

Form:Solid

Specifications

Spezifikationen & Reinheit

≥99%

Biochemische und physiologische Mechanismen

Triamterene-d 5 is deuterium labeled Triamterene, which can block epithelial Na+ channel (ENaC) in a voltage-dependent manner, which used as a mild diuretic.

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

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

Reinheit

≥99%

Namen und Kennungen

Kanonisches Lächeln

NC1=NC2=NC(N)=NC(N)=C2N=C1C3=C([2H])C([2H])=C([2H])C([2H])=C3[2H]

Molekulargewicht

258.29

Application Protocols

• Not applicable for immunoassay formats (WB, IHC, IF, FC) as this is a small-molecule standard.
• Analytical protocol outline (general, LC–MS/MS)
  • Prepare a primary stock in methanol or DMSO (e.g., 1 mg/mL). Serially dilute with methanol:water (1:1) containing 0.1% formic acid to prepare calibration working solutions.
  • Spike a fixed amount of Triamterene-d5 into all calibration standards, QCs, and samples prior to extraction.
  • Extract by protein precipitation (3 volumes ACN), vortex 1 min, centrifuge (≥12,000 × g, 10 min), transfer supernatant, dilute with water, and inject 1–10 µL.
  • Quantify using MRM with the internal standard response ratio (analyte/IS). Validate linearity, accuracy, precision, recovery, matrix effect, and stability per your laboratory SOPs. Note: The above is general guidance; adapt to your method and regulatory framework. Item-specific tested applications are not provided for this product.

Biological Roles

• Item-specific biological data: Not specified for this item; refer to primary literature if needed.
• Context (general, non-clinical)
  • Triamterene is a well-known small molecule; the deuterated analog (Triamterene-d5) is used as a tracer/internal standard in bioanalytical chemistry. The deuterium label is biologically silent—no change in target binding or mechanism is intended or relied upon for research uses.
• Use in biochemistry workflows (analytical)
  • Quantification of triamterene in plasma, urine, or tissue homogenates by isotope-dilution LC–MS/MS.
  • Assessment of extraction recovery, matrix effects, and stability in ADME sample processing. Spiking Triamterene-d5 before sample workup enables accurate correction for losses and ion suppression/enhancement.
• Metabolic considerations (general)
  • Deuterium is located on non-exchangeable aromatic positions in typical d5 analogs, minimizing back-exchange in biological matrices. Consequently, the internal standard tracks the analyte through extraction, chromatographic separation, and ionization.
• Notes
  • No biological activity claims are made for this product. For research use only, consistent with the product’s Research Use Note.

Buffer Applications

• This compound is not a buffering agent and is not typically used to prepare pH buffer systems.
• Practical analytical note
  • For LC–MS/MS assays, common mobile phase buffers/acids are volatile additives such as formic acid (0.1% v/v) or ammonium formate/acetate (2–20 mM) to enhance ionization and chromatographic performance of triamterene-class analytes. Select additive strength to balance sensitivity and peak shape.
• Preparation tip
  • Dissolve Triamterene-d5 in an organic cosolvent (e.g., methanol or DMSO) before dilution into buffered aqueous mobile phases to avoid precipitation.

Green Alternatives

• Context
  • As an isotopically labeled analytical standard, the main “green” considerations involve solvent choice, scale minimization, and waste handling rather than replacing the compound itself.
• Greener solvent strategies (general)
  • Prefer methanol over acetonitrile when chromatographic performance allows; MeOH is generally considered a greener protic solvent with lower life-cycle impact.
  • Use water-rich mobile phases where solubility and retention permit; optimize gradient to minimize organic consumption.
  • For sample prep, consider aqueous protein precipitation (MeOH:water) or micro-SPE formats to reduce solvent volumes.
• Process and waste minimization
  • Work at the lowest effective concentrations and volumes for calibration curves (e.g., microliter aliquots for ng/mL standards).
  • Adopt 96-well microplate workflows and evaporate under nitrogen at ambient or mild temperatures to reduce energy use.
• Materials selection
  • Utilize recyclable polypropylene vials and low-dead-volume inserts to cut plastic waste; avoid PTFE where not essential.
• Trade-offs
  • Methanol can increase ion suppression in some matrices relative to acetonitrile; perform matrix-effect assessments. Water-rich phases may reduce solubility; balance greenness with method robustness and quantitative performance.

Pharmaceutical Uses

• This product is supplied for research use only. No therapeutic or clinical use is claimed or implied.
• Typical roles in pharmaceutical R&D and QC (general)
  • Stable-isotope internal standard for method development and validation in bioanalysis (nonclinical and clinical sample testing conducted by qualified laboratories), dissolution testing, and stability studies of dosage forms containing triamterene.
  • System-suitability and performance tracking in LC–MS/MS assays: response factor monitoring, retention time locking, and recovery correction across batches and instruments.
  • Reference material in impurity profiling, forced-degradation studies, and extractables/leachables assessments where coelution and ionization parity are advantageous.
• Documentation
  • For regulated environments, maintain full chain-of-custody and characterization package (CoA including isotopic enrichment, purity, and identity by MS/NMR). Establish storage and handling SOPs for isotope-labeled standards to ensure data integrity.
• Compendial status
  • No pharmacopeial monograph is expected for the d5 analog. Use against internally qualified acceptance criteria. The unlabeled API may have compendial references; the isotope standard serves as an auxiliary analytical material.

Physical Properties

• Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/general properties for the non-deuterated parent (Triamterene) — deuteration minimally alters these bulk properties but increases exact mass:
  • Appearance: yellow to orange crystalline solid (literature, parent compound).
  • Melting point: high, reported >300 °C with decomposition (literature, parent compound). Exact value varies by source; handle as a thermally robust, decomposing solid.
  • Solubility: practically insoluble in water; soluble in polar aprotic organics such as DMSO and DMF; sparingly to moderately soluble in methanol and ethanol with heat/sonication (literature trends, parent compound). For LC–MS use, stocks are commonly prepared in MeOH or DMSO.
  • Acid–base: weakly basic/anilino nitrogens; multiple ring nitrogens reduce overall basicity (literature, parent compound). Apparent pKa values depend on site; expect limited ionization at neutral pH.
  • LogP/logD: moderate lipophilicity reported for parent scaffold (literature, parent compound); deuteration has negligible effect on partitioning within experimental error.
  • UV–vis: conjugated heteroaromatic chromophore with UV absorbance in near-UV range (literature, parent compound); useful for HPLC–UV tracking, but LC–MS/MS is preferred for quantitative work. Note: Treat all numerical values as literature guidance for the non-deuterated parent. For this specific lot’s definitive specifications, consult the CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Isotopic labeling considerations (general for “-d5” analytes)
  • Isotopic enrichment and labeling pattern: For quantitative LC–MS/MS, a high deuterium incorporation and a defined labeling site (often phenyl-d5 for aromatic drugs) are desirable to ensure coelution and similar ionization as the analyte. Actual enrichment level and labeling map are item-specific: Not specified for this item; refer to CoA/Spec Sheet.
  • Residual protium content and potential H/D exchange: Deuteriums on non-exchangeable aromatic carbons are stable under typical analytical conditions; ensure mobile phases lack strong acids/bases that could promote exchange at any labile sites (if present).
• Analytical suitability
  • Stable-isotope internal standards are typically supplied at high chemical purity with low levels of isobaric interferences to support MRM quantitation. For this item, detailed impurity/assay data are Not specified; refer to CoA.
• Documentation and release testing
  • Request CoA for: chemical purity (%), isotopic enrichment (%D), residual solvents, identification (NMR/MS), and chromatographic profile (LC–MS/HPLC). If performing regulated bioanalysis, ensure qualification against acceptance criteria (matrix-matched recovery, relative response factor, and stability).

Reaction and Applications

• Primary application (analytical chemistry)
  • Triamterene-d5 is principally used as a stable-isotope internal standard for quantitative determination of triamterene in biological fluids, environmental samples, and dosage forms by LC–MS/MS. The d5 label closely tracks chromatographic behavior and ionization efficiency, enabling accurate isotope-dilution assays.
• LC–MS/MS method notes (general)
  • Ionization: positive-mode ESI typically affords strong [M+H]+ signals for triamterene-class compounds.
  • Transitions: choose MRM transitions shifted by +5 Da relative to the analyte. Optimize collision energies empirically to avoid overlap with natural isotopic envelope.
  • Sample prep: protein precipitation (MeOH or ACN), SPE on mixed-mode cation-exchange cartridges, or dilute-and-shoot for clean matrices. Spike internal standard prior to extraction to correct recovery.
• Other laboratory uses
  • Metabolic stability and permeability assays as a tracer molecule; matrix effect evaluation and instrument performance checks.
• Synthetic chemistry context (secondary)
  • As a polyaminated heteroaromatic, the scaffold can undergo acylation/alkylation of exocyclic amines under mild base and coupling conditions; however, the d5 material is rarely used for synthetic transformations due to its analytical value.
• Practical guidance
  • Prepare single-use aliquots to preserve isotopic integrity. Confirm absence of in-source H/D exchange under your LC–MS conditions by monitoring mass shifts across pH/mobile phase variants.

Reaction Conditions

• Not typically used as a synthetic reagent. This section provides general analytical-method conditions relevant to the compound’s most common use (LC–MS/MS internal standard):
• LC–MS/MS (general literature practice)
  • Mobile phases: A = water + 0.1% formic acid (or 2–10 mM ammonium formate, pH ~3–4); B = acetonitrile or methanol.
  • Gradient: start 10–30% B, ramp to 70–95% B over 2–6 min depending on column and desired retention; re-equilibrate adequately.
  • Column: C18 or phenyl-hexyl, 2.1 × 50–100 mm, 1.7–3 µm. Column temp 30–50 °C.
  • Flow rate: 0.2–0.5 mL/min (UHPLC 2.1-mm ID).
  • Detection: ESI(+), monitor MRM transitions offset by +5 Da from triamterene. Optimize declustering potential and collision energy empirically.
• Sample preparation (general)
  • Spike Triamterene-d5 before extraction. Perform protein precipitation with 3–4 volumes of cold ACN or MeOH; vortex, centrifuge, and collect supernatant. Optionally, SPE (mixed-mode cation exchange) to improve cleanliness.
  • Working solution stability: assess at room temperature (bench-top), autosampler (4–10 °C), and freeze–thaw over at least 3 cycles. Note: Numerical instrument parameters and transitions should be optimized in your lab; values above are general guidance, not item-specific specifications.

Safety and Handling

• GHS/Classification (item-specific): Not specified for this item; refer to SDS for authoritative hazard information.
• General handling guidance (good laboratory practice)
  • Avoid inhalation of dust and contact with skin/eyes. Use in a fume hood or ventilated enclosure when weighing powders.
  • Personal protective equipment: lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid generating aerosols; use antistatic tools for microgram/milligram handling.
  • Hygiene: wash hands after handling; do not eat or drink in the lab.
• Storage incompatibilities and precautions (general)
  • Store tightly sealed, protected from moisture. Aromatic amines/heteroaromatics can exhibit light sensitivity; store in amber containers or protect from strong light as a precaution.
  • Separate from strong oxidizers and strong acids. Avoid prolonged elevated temperatures.
• First-aid overview (general, not a substitute for SDS)
  • Inhalation: move to fresh air; seek medical advice if symptoms persist.
  • Skin/eye contact: rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
• Deuterated materials
  • Isotopic substitution does not materially change acute hazards relative to the unlabeled analog. Treat as you would the parent compound, following the SDS.

Solvent Selection

• Polarity/behavior (general, based on parent scaffold)
  • Aromatic, heteroatom-rich base with very low water solubility. Best handled in polar aprotic organics.
• Recommended solvents for stock solutions (analytical use)
  • DMSO: excellent solvating power; prepare concentrated stocks (e.g., 1–10 mg/mL) and dilute into sample diluent.
  • Methanol or acetonitrile: suitable for LC–MS/MS working solutions; may require sonication or gentle warming to fully dissolve.
  • DMF: strong solvent for difficult dissolutions; follow with dilution into LC-compatible media.
• Miscibility and sample-compatibility notes
  • For biological matrices, final organic content is typically kept ≤30–50% to prevent precipitation during spiking. Use methanol:water or acetonitrile:water with 0.1% formic acid for positive-ion ESI methods (general LC–MS practice).
• When to choose alternatives
  • If adsorption losses are observed at low ng/mL, add small amounts of organic modifier or BSA-free carrier, or use silanized glass/PP vials. If matrix effects are severe, consider matrix-matched calibration with the same internal standard.
• Practical tips
  • Filter working solutions (0.2 µm PTFE) if particulates form. Avoid aqueous-only vehicles due to poor solubility of the parent scaffold. Verify solution clarity before quantitative use.

Storage and Reconstitution

• Item-specific storage and shipping
  • Storage Conditions: Store at -20°C (item-specific).
  • Shipped In: Ice chest + Ice pads (item-specific), to maintain low temperature during transit.
• General handling and reconstitution
  • Allow the sealed container to equilibrate to room temperature before opening to minimize moisture condensation.
  • Reconstitution solvents: methanol, acetonitrile, or DMSO are recommended for stock solutions. Water alone is not recommended due to low solubility of the parent scaffold.
  • Suggested stock concentrations (general): 1–10 mg/mL. Filter if particulates remain (0.2 µm PTFE) and verify clarity.
  • Aliquoting: prepare single-use aliquots in amber vials to avoid repeated freeze–thaw and potential light exposure.
• Stability guidance (general)
  • Store solid at -20°C in a desiccated, light-protected environment. For solutions, refrigerate (2–8 °C) for short-term autosampler use and freeze (-20 °C) for longer-term storage; confirm stability under your conditions.
  • Avoid repeated freeze–thaw cycles; discard aliquots that show precipitation or degradation by LC–MS.
• Documentation
  • Label all aliquots with concentration, solvent, and preparation date. For this specific item’s shelf life and solution stability, Not specified; refer to CoA/Spec Sheet.
• Research Use Note: For research use only (item-specific).

Structure and Identity

• Item-specific identifiers
  • CAS: 1189922-23-3 (item-specific)
  • SKU: T651384 (item-specific)
  • 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.
• Compound type and scaffold (general/literature)
  • Triamterene is a pteridine-derived, polyaminated heteroaromatic bearing a substituted anilide/phenyl moiety. The “-d5” denotes a deuterium-labeled analog (typically ring-deuterated on the phenyl substituent) used as a stable-isotope internal standard.
  • Core functional groups (parent scaffold): diaminopteridine ring system (multiple ring nitrogens, two exocyclic amines) conjugated to a para-substituted phenyl bearing additional amino substitution. The framework is highly heteroatom-rich and weakly basic due to ring nitrogens and anilino amines.
• Stereochemistry (general)
  • No stereogenic centers; planar, conjugated, polyaza aromatic system with an appended phenyl ring.
• 2D structural description (general)
  • A bicyclic pteridine nucleus (fused 1,3,5-triazine–pyrazine-like arrangement) substituted with exocyclic –NH2 groups and connected via a C–C bond to a para-aminophenyl ring. The deuterated analog replaces five protium atoms (commonly on the phenyl ring) with deuterium, preserving electronic structure while increasing exact mass by ~5 Da (literature).

Synthetic Utility

• General reactivity (based on parent scaffold)
  • Polyaminated, electron-deficient heteroaromatic (pteridine-like) framework with exocyclic anilino amines. Potential transformations include selective N-acylation/alkylation, diazotization of anilines under strongly acidic conditions (controlled), and electrophilic substitution on the phenyl ring (less activated due to anilino substitution and conjugation).
  • Metal-catalyzed cross-couplings are not typical for this fully formed scaffold; functionalization usually targets the amine groups if derivatization is required.
• Relevance to the d5 analog
  • Because Triamterene-d5 is primarily an analytical standard, it is rarely subjected to synthetic modification. Any chemical derivatization risks scrambling or diluting isotopic labeling and is generally avoided.
• Retrosynthetic perspective (general)
  • Construction of the parent scaffold involves condensation routes to the pteridine core followed by introduction of the anilino moiety. For labeled analogs, the deuterium is commonly introduced via use of a pre-deuterated aryl precursor (e.g., phenyl-d5) to ensure non-exchangeable labeling.
• Practical note
  • If chemical modification is necessary (e.g., to create calibration surrogates), validate isotopic integrity post-reaction by high-resolution MS and 2H NMR.

Target Specificity

• Not applicable. This product is a small-molecule chemical standard, not an antibody or affinity reagent. No antigen, clone, isotype, or species reactivity data apply.