Methiocarb-d , CAS No.1581694-94-1

CAS: 1581694-94-1 Cat. No.: M1450765 Formule: C₁₁H₁₂D₃NO₂S Poids moléculaire: 228.33 Numéro CE: 808-689-7 PubChem CID: 117065427

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Vue d’ensemble

Methiocarb-d 3 is the deuterium labeled Methiocarb.

Specifications

Conditions de stockage de stockage

Store at -20°C

Expédié en

Ice chest + Ice pads

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Noms et identifiants

• Sourires canoniques: CC1=CC(=CC(=C1SC)C)OC(=O)NC
• IUPAC Name: (3,5-dimethyl-4-methylsulfanylphenyl) N-(trideuteriomethyl)carbamate
• InChIKey: YFBPRJGDJKVWAH-HPRDVNIFSA-N
• INCHI: 1S/C11H15NO2S/c1-7-5-9(14-11(13)12-3)6-8(2)10(7)15-4/h5-6H,1-4H3,(H,12,13)/i3D3
• Isomères SMILES: [2H]C([2H])([2H])NC(=O)OC1=CC(=C(C(=C1)C)SC)C
• PubChem CID: 117065427
• Poids moléculaire: 228.33

Application Protocols

No manufacturer-validated application protocols are provided for this item.

For general use as an internal standard in LC–MS/MS quantitation of methiocarb, refer to the Reaction & Applications and Reaction Conditions sections for high-level guidance, and consult your laboratory’s validated SOPs for details on calibration curve preparation, matrix-matched standards, and quality controls.

Biological Roles

Item-specific biological data are not provided. The following summarizes the parent compound’s roles (literature/general) to contextualize research uses of the deuterated analog.

• Mode of action (parent methiocarb): carbamate inhibitor of cholinesterases in invertebrates and vertebrates; reversible carbamylation of the active-site serine of acetylcholinesterase.
• Environmental behavior (general): moderately lipophilic aromatic carbamate; subject to hydrolysis and oxidative metabolism; transformation can yield phenolic and sulfoxide/sulfone derivatives.
• Biotransformation (general): oxidative S-oxidation (to sulfoxide/sulfone), O-dealkylation of the carbamate, and hydrolysis to give the corresponding phenol and methylamine derivatives.
• Analytical implication: deuterated methiocarb provides a mass-resolved internal standard for quantifying parent methiocarb in complex biological or environmental matrices, enabling normalization for recovery and matrix effects.

Caveat: This product is designated for research use only. No medical, diagnostic, or therapeutic applications are intended or implied.

Buffer Applications

This product is not a buffering agent. It does not form conventional laboratory buffer systems.

Practical note:

• When used as an analytical standard for LC–MS, prepare working solutions in LC-compatible mobile phases (e.g., water/ACN or water/MeOH with 0.1% formic acid or ammonium formate), after initial dissolution in organic solvent. Avoid high-pH buffers that can accelerate carbamate hydrolysis.

Green Alternatives

Greenness considerations center on solvent use and sample preparation, since the compound is an analytical standard rather than a bulk reagent.

Greener choices and tradeoffs (general guidance):

• LC–MS mobile phases/diluents: • Prefer methanol over acetonitrile when chromatographic performance permits; MeOH has lower life-cycle environmental impact and broader availability. Tradeoff: possible lower sensitivity or broader peaks for some analytes. • Use aqueous buffers with volatile, low-toxicity modifiers (e.g., formic acid, ammonium formate) at the lowest effective concentrations.

• Sample preparation: • Miniaturize extraction (µSPE, SPME) to reduce solvent volumes compared to traditional LLE. • Consider QuEChERS with reduced ACN volumes and salt loads; validate recovery and precision with the deuterated IS. • Explore alternative solvents (e.g., ethanol or ethyl acetate) for certain matrices where performance is acceptable.

• Waste minimization: • Prepare concentrated stocks and aliquot to extend life and reduce remake frequency. • Pool low-concentration wastes from calibration and rinse solutions for a single disposal stream.

Quick comparison (illustrative):

• Acetonitrile vs Methanol for standards • EHS profile: MeOH greener; ACN more hazardous and supply-sensitive. • Performance: ACN often superior peak shape/response for aromatic carbamates; MeOH acceptable with method tuning (column choice, temperature, gradient).

Overall: The most impactful “green” lever is reducing total organic solvent use via microextraction and efficient chromatographic methods, while maintaining data quality through isotope dilution.

Pharmaceutical Uses

No pharmacopeial or excipient roles are specified for this item. As a deuterated analog of a pesticide active, it is not used as a pharmaceutical ingredient.

Relevant research/manufacturing context (general):

• Serves as an internal standard for analytical quality control of residues in raw materials or process environments where pesticide contamination must be monitored.
• Can support method validation (specificity, linearity, precision, accuracy) in regulated laboratories; however, this listing provides no GMP or pharmacopeial compliance claims. Refer to your QA requirements and the item’s CoA for suitability.

Physical Properties

Item-specific specifications are not provided in the Product Data for this deuterated standard. Consult the CoA/Spec Sheet for definitive values.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Note: will exceed that of unlabeled methiocarb by the number of 2H atoms.)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. • Typical for unlabeled methiocarb (literature): solid, mp ~106–108 °C.
• Boiling point/decomposition: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable/Not specified for this item.
• pKa: Not applicable (carbamate; no strongly ionizable center in neutral range) – general statement.
• logP/logD: Not specified for this item; refer to CoA/Spec Sheet. • Unlabeled methiocarb is moderately lipophilic (literature, qualitative).
• Solubility (qualitative guidance): • Poorly soluble in water (literature, for parent). • Soluble in common organic solvents used for analytical standards (MeOH, acetonitrile, acetone, ethyl acetate) (literature, for parent).
• UV/Vis: Not specified for this item; refer to CoA/Spec Sheet. (Aromatic ring generally exhibits UV absorbance; deuteration negligibly alters λmax.)

Note: Deuteration has negligible effect on bulk physical behavior, but slightly shifts exact mass and sometimes vapor pressure/volatility; analytical retention can differ subtly from the unlabeled analog.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Considerations specific to deuterated analytical standards:

• Isotopic enrichment and labeling pattern: For quantitative LC–MS/GC–MS, high deuterium incorporation at defined positions minimizes bias from isotope effects. Verify isotopic purity (e.g., %D, pattern) on the CoA.
• Chemical purity: Residual unlabeled parent, positional isomers, or partially deuterated species can influence calibration accuracy. Review GC/LC purity and MS data on the CoA.
• Water and residual solvents: Moisture can promote carbamate hydrolysis; low water content is preferred for long-term stability. Exact limits are not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If present, stabilizers may influence UV background or MS ionization; account for them during method development.

What the grade typically implies (general guidance):

• Analytical/reference standard grade is optimized for trace analysis, with documentation of identity (NMR/MS), purity profile, and isotopic enrichment. Low, consistent background for LC–MS is expected.

Recommendation:

• For quantitative work, retain batch-specific CoA and, if needed, verify isotopic purity by HRMS. Prepare calibration solutions gravimetrically using an internal standard approach.

Reaction and Applications

Primary application domain (for deuterated methiocarb): quantitative analytical chemistry.

• Isotope-dilution mass spectrometry (IDMS): • Serves as an internal standard to correct for matrix effects, ion suppression, and extraction losses when quantifying methiocarb in environmental, food, or biological samples. • Ideal for LC–ESI–MS/MS with multiple reaction monitoring (MRM). Deuterium labels shift precursor/product m/z without changing fragmentation pathways.

• Method development and validation: • Calibration: prepare multi-level external calibrators of unlabeled methiocarb and spike a constant amount of Methiocarb-d to each level and samples; regress analyte/IS area ratios. • Recovery and matrix studies: spike pre- and post-extraction to assess extraction efficiency and matrix suppression.

• Tracer studies (general): • Can support adsorption/partitioning or degradation studies by enabling unambiguous mass-resolved tracking of the labeled species relative to background.

• Practical tips: • Use dry solvents and minimize exposure to strong acids/bases; carbamate hydrolysis yields phenolic and amine fragments that confound quantitation. • Confirm that the deuteration pattern avoids exchangeable positions under your mobile phase conditions; if exchangeable, consider temperature and aqueous content to limit D/H back-exchange. • Evaluate co-elution of labeled and unlabeled peaks; partial separation is acceptable in MS, but identical chromatography simplifies matrix compensation.

Note: Synthetic/transformational chemistry applications are limited; this material is typically not used as a reagent but as a labeled reference standard.

Reaction Conditions

No item-specific reaction conditions are provided since the product is an analytical standard rather than a reagent. The following general conditions pertain to analytical use and to parent-compound behavior.

Analytical preparation (general guidance):

• Stock solutions: 0.1–1.0 mg/mL in acetonitrile or methanol; prepare under dry conditions; store at −20 °C in amber vials with minimal headspace.
• Working solutions: dilute into mobile phase (e.g., 50:50 water:ACN + 0.1% formic acid) immediately prior to analysis.

LC–MS/MS (literature-informed, general for methiocarb):

• Ionization: ESI+ often yields strong response; monitor protonated molecule and characteristic fragments. ESI− may also be feasible depending on method.
• Chromatography: C18 or phenyl-hexyl columns; gradients from 20–90% organic (ACN or MeOH) over 5–15 min; column temp 30–40 °C.
• Sample preparation: QuEChERS extraction for food matrices; SPE (C18, HLB) for water/biological matrices. Spike Methiocarb-d prior to extraction to track recoveries.

Chemical transformations (parent compound, literature):

• Hydrolysis: accelerated under alkaline or strong acidic conditions (e.g., pH > 9 or strong mineral acid) with increased temperature and water activity.
• Oxidation: thioether oxidizes with peracids or H2O2 catalysts to sulfoxide/sulfone; avoid oxidizing environments during storage/analysis.

Note: Validate all conditions for your specific instruments and matrices. The above are general guidelines, not item specifications.

Safety and Handling

Safety data for this specific item are not provided; consult the SDS for authoritative guidance. As a deuterated analog of methiocarb (a carbamate pesticide), apply stringent laboratory hygiene and controls.

• GHS classification, pictograms, H-statements: Not specified for this item; refer to SDS.
• Signal word: Not specified for this item; refer to SDS.

General hazards (literature/parent compound):

• Carbamate esters can inhibit cholinesterase enzymes. Avoid inhalation, ingestion, and skin/eye contact. Handle in a fume hood with appropriate containment.

Recommended PPE and controls:

• Use lab coat, nitrile gloves (change frequently), splash goggles. For weighing solids/particulates, use a balance enclosure or glovebox as appropriate.
• Employ closed-transfer techniques for stock solutions; avoid aerosolization.

Storage incompatibilities and stability:

• Store segregated from strong acids/bases and oxidizers. Carbamates can hydrolyze under strongly acidic/basic or high-moisture conditions; keep containers tightly closed.
• Avoid prolonged exposure to light and elevated temperatures.

First-aid overview (general):

• Skin/eye contact: Immediately rinse with water for ≥15 min; remove contaminated clothing; seek medical attention per SDS guidance.
• Inhalation: Move to fresh air; monitor; obtain medical attention.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Waste and decontamination:

• Collect as hazardous organic waste. Decontaminate surfaces with appropriate organic solvent followed by detergent wash, observing institutional EHS procedures.

Always defer to the item-specific SDS and institutional policies.

Solvent Selection

Methiocarb-d is a moderately nonpolar/aromatic carbamate that behaves similarly to the unlabeled parent in solvent choice. For analytical standards, solvent selection balances solubility, stability, and MS compatibility.

• Primary diluents (analytical practice): • Acetonitrile (ACN): excellent for LC–MS; low viscosity, strong elution strength; good stability of carbamates; miscible with water. • Methanol (MeOH): LC–MS compatible; slightly protic; can modestly accelerate hydrolysis under strong base; generally acceptable for short-term standards. • Acetone or ethyl acetate: good solubility; not preferred as long-term LC–MS diluents due to volatility or background.
• Water: poor solubility expected (literature, for parent). Use aqueous mixtures only after dissolving in organic solvent.
• Dielectric/polarity (general): parent methiocarb is moderately lipophilic; deuteration does not materially change solvent affinity.

Selection tips:

• For stock standards (e.g., 0.1–1 mg/mL), use dry ACN or MeOH; purge with inert gas, and store at −20 °C in amber vials with PTFE-lined caps.
• For working solutions, match the instrument mobile phase (e.g., 50:50 ACN:H2O + 0.1% formic acid) to minimize solvent effects on peak shape.
• Avoid high-pH aqueous media which can promote carbamate cleavage.

Comparison (general):

• ACN vs MeOH: ACN often yields sharper peaks and slightly higher MS response for aromatic carbamates; MeOH may offer better solubility for some matrices but can broaden peaks in high aqueous phases.

Storage and Reconstitution

• Storage conditions (item-specific): Store at −20 °C.
• Shipping (item-specific): Shipped in an ice chest with ice pads to maintain cold chain.
• Container: Keep tightly closed in amber, chemically resistant vials with PTFE-lined caps to minimize permeation and adsorption.

Reconstitution and handling (general guidance):

• Initial dissolution: Use dry acetonitrile or methanol to prepare a concentrated stock solution. Sonication may aid dissolution if solid.
• Aliquoting: Dispense single-use aliquots to minimize freeze–thaw cycles and headspace; backfill with inert gas if feasible.
• Working solutions: Prepare immediately before use by diluting into LC–MS mobile phase or sample prep solvent. Avoid high-pH media that may accelerate carbamate hydrolysis.
• Stability: Item-specific stability data are not provided; refer to the CoA/Spec Sheet. As general practice, store stocks at −20 °C and protect from light and moisture; monitor by LC–MS for degradation (new peaks, loss of response).

Research Use Note: For research use only. Not for human or veterinary use.

Structure and Identity

Overview: Methiocarb-d is a deuterium-labeled analog of the carbamate pesticide methiocarb, intended for research and analytical use (e.g., isotope-dilution LC–MS/MS). The exact deuteration pattern is not specified for this item.

• SKU: M1450765
• Product name: Methiocarb-d (deuterium-labeled methiocarb)
• CAS: 1581694-94-1 (item-specific)
• PubChem CID: 117065427 (item-specific)
• InChIKey: 435647 (item-specific; truncated/short form as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural description (general, literature):

• Parent scaffold: methiocarb is an O-aryl N-methylcarbamate derived from a substituted phenol.
• Aromatic ring: 3,5-dimethyl-4-(methylthio)phenyl moiety linked via an O–carbamate to an N-methyl group.
• Functional groups: aryl thioether (–S–CH3), two ring methyl substituents, phenoxy carbamate (–O–C(=O)–N–CH3).
• Isotopic labeling: deuterons (2H) replace one or more hydrogen atoms on the parent structure (sites not specified for this product). This preserves core connectivity while shifting exact mass and improving isotope-dilution quantitation.

Stereochemistry: None inherent in the parent methiocarb core (achiral as a single molecule); deuteration does not introduce stereocenters when installed at non-stereogenic positions.

Synthetic Utility

As a deuterium-labeled analog intended for analytical use, Methiocarb-d is not commonly employed as a synthetic reagent. Nevertheless, a few research-oriented utilities exist:

• Isotope-tracing in degradation pathways: Use in controlled hydrolysis or oxidation studies to confirm product identities (e.g., whether deuterium resides on the aromatic ring or N-methyl group) by MS isotopologue analysis.
• Internal standard in multistep sample preparation: Deuterated internal standard normalizes losses during solid-phase extraction, liquid–liquid extraction, or QuEChERS cleanups, indirectly supporting synthetic/derivatization workflows (e.g., pre-column derivatization for GC when applied to related carbamates).

Functional group perspective (general, parent compound):

• Aryl carbamate: susceptible to base- or acid-catalyzed cleavage; stable under neutral, anhydrous conditions.
• Thioether: oxidizable to sulfoxide/sulfone, enabling mechanistic oxidation studies.

Conclusion: Select this product for isotope-dilution analytics and mechanistic tracing, not as a building block or reagent in preparative synthesis.

Target Specificity

Not applicable. This product is a small-molecule analytical standard, not a biological targeting reagent (e.g., antibody, enzyme inhibitor standard with defined target binding data). No antigen/epitope, clone, isotype, or species reactivity information applies.