6-Hydroxynaloxone-d , CAS No.H1440413

CAS: H1440413 Cat. No.: H1440413 Formula: C₁₉H₂₀D₃NO₄ Molecular Weight: 332.41

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

6-Hydroxynaloxone-d 3 is deuterated labeled 6-Hydroxynaloxone.

Specifications

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

Molecular Weight

332.41

Application Protocols

No manufacturer-validated protocols are provided for this item. The following are general, literature/practice-based suggestions for using deuterated small-molecule internal standards in LC–MS/MS. Adapt to your specific methods and validation requirements.

Suggested workflow (research use):

• Stock preparation: dissolve at 0.5–1 mg/mL in methanol or acetonitrile. Sonicate briefly if needed. Record exact concentration gravimetrically.
• Aliquoting: dispense single-use aliquots (e.g., 50–200 µL) in amber vials; store at −20 °C.
• Working internal standard: dilute with water/0.1% formic acid or 10–50% MeOH/ACN to target concentration (e.g., low ng/mL to µg/mL depending on assay).
• Sample spiking: add ILIS to each sample, calibration standard, and QC before protein precipitation (ACN or MeOH) or SPE. Maintain constant ILIS concentration across the batch.
• LC–MS/MS setup: monitor MRM transitions that reflect the deuterated mass shift; verify absence of cross-talk with the native analyte’s isotopic envelope.
• Quality controls: include matrix-matched QCs at multiple levels; assess carryover and matrix effects per standard bioanalytical guidance.

Documentation: capture preparation records, lot numbers, and stability checks. All steps should be performed under approved institutional SOPs.

Biological Roles

Contextual, literature-based description for the 6‑hydroxynaloxone chemotype; not product-specific claims.

• Structural/functional class: morphinan-derived opioid receptor ligand, bearing a tertiary amine and phenolic functionality. The 6‑hydroxy substitution increases polarity relative to naloxone.
• Biochemical relevance: phenolic morphinans interact with opioid receptors (mu, kappa, delta). Hydroxylated metabolites are often monitored in research to elucidate metabolic pathways, phase II conjugation (e.g., glucuronidation), and structure–activity relationships.
• Metabolism context: in vitro systems (microsomes, hepatocytes) can yield 6‑hydroxylated products via oxidative biotransformation; deuterated analogs serve as mass spectrometric surrogates for accurate quantitation of these metabolites in complex matrices.
• Transport/ADME considerations (general): tertiary amine protonation at physiological pH influences distribution and potential transporter interactions; phenolic OH can undergo conjugation, altering clearance pathways.

Important notes:

• This item is provided strictly for research use only.
• No medical, diagnostic, or therapeutic claims are made or implied for this product.
• Actual receptor affinity, intrinsic activity, and biological potency for the specific deuterated species are not specified for this item; consult primary literature if such data are required for your study design.

Buffer Applications

This product is a small-molecule reference standard rather than a buffering agent. It is not used to establish or maintain pH.

Practical note for analytical workflows:

• When preparing working solutions, volatile, MS-compatible buffers (e.g., 5–10 mM ammonium formate/acetate, 0.1% formic acid) are commonly employed to support LC–MS analysis of phenolic/amine-containing small molecules. Select buffer strength and pH to optimize chromatographic retention and ionization of your target analyte.

For buffer recipes, use dedicated buffering reagents (e.g., phosphate, acetate, formate) rather than this compound.

Green Alternatives

For deuterated analytical standards, environmental impact is dominated by solvent selection and sample preparation rather than reagent choice. Greener practices focus on minimizing solvent volumes, choosing less hazardous solvents, and optimizing workflows.

Greener choices and trade-offs (general guidance):

• Replace acetonitrile with methanol/water when chromatographic selectivity allows.
• Use aqueous buffers at low ionic strength (e.g., 5–10 mM ammonium formate/acetate) to maintain MS compatibility while reducing salt load.
• Miniaturize: adopt microelution SPE or 96‑well protein precipitation to reduce solvent usage per sample.
• Explore core–shell or sub‑2 µm columns to shorten run times and reduce solvent consumption without compromising separation.
• Avoid halogenated solvents entirely for solution prep and cleanup.

Comparison snapshot (literature/practice-based; not specifications):

• Methanol: lower toxicity profile, renewable feedstock potential, excellent ESI performance; may require higher pressures or temperature to match ACN elution strength.
• Acetonitrile: strong eluotropic strength and narrow peaks; higher waste impact and supply volatility.
• Water with 0.1% formic acid: simplest, greenest diluent for working standards; ensure compound stability against acid-catalyzed changes.

Operational tips:

• Prepare concentrated stocks to limit repeat solvent use; aliquot and store at −20 °C to extend life.
• Validate shorter gradients and multiplexed injections to decrease total solvent per sample while maintaining data quality.

Pharmaceutical Uses

This listing is for a research-use-only deuterated reference standard and is not intended for human or veterinary use. No clinical or therapeutic claims are made.

Relevant roles in pharmaceutical R&D and QC (general context):

• Reference standard: used to support method development and validation for quantitation of 6‑hydroxylated naloxone species in nonclinical studies, formulation investigations, and stability-indicating assays.
• Process/impurity tracking: assists in identifying and tracking hydroxylated impurities or degradation products in synthetic or formulated materials of related chemotypes.
• Calibration and system suitability: deuterated internal standards are widely applied in LC–MS/MS calibration curves, QC samples, and system suitability checks to ensure method robustness and instrument performance.
• Biosample analysis: supports pharmacokinetic and metabolism research by correcting for matrix effects and extraction recovery in bioanalytical workflows (research context).

Documentation expectations:

• Batch-specific CoA detailing chemical purity, isotopic enrichment, and identification data.
• Storage and stability information to define re-test periods and solution shelf life.

Any references to pharmacopeial status, compendial monographs, or acceptance criteria are Not specified for this item; refer to your internal method validation and regulatory guidance as applicable.

Physical Properties

Only limited item-specific properties are provided in the product data. Do not treat literature values as product specifications.

Item-specific:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Typical/literature properties for 6‑hydroxylated naloxone analogs (for context; not specifications):

• Form: usually a solid or film-forming solid for reference standards; often provided neat or as a film in amber vials (literature/general handling practice)
• Ionization: tertiary amine pKa typically in the 8–9 range; phenolic OH pKa typically ~9–10, supporting good solubility as salts in aqueous acidic media and moderate solubility in polar organics (literature for naloxone-like compounds)
• LogP/logD: neutral base cLogP commonly in the ~2–3 range; logD at pH 7.4 reduced due to partial protonation (literature/analogue comparison)
• Solubility (qualitative): readily soluble in methanol, acetonitrile, and DMSO; increased aqueous solubility upon acidification (e.g., 0.1% formic acid) due to amine protonation (general practice in LC–MS)
• UV absorbance: aromatic system provides UV activity in the 210–230 nm and 270–285 nm regions; exact ε not specified (literature observation)

Note: Exact melting point, water content, refractive index, and other analytical attributes are Not specified for this item; refer to CoA/Spec Sheet and SDS for authoritative data.

Quality and Grades

Item-specific grade/purity are not provided in the product data.

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

Interpretation and best practices for deuterated reference standards (general guidance):

• Chemical purity versus isotopic purity: For isotopically labeled standards, two metrics are typically reported. Chemical purity (e.g., HPLC/UPLC assay, residual solvents) and isotopic enrichment (e.g., D-content at specified sites). The latter directly affects mass spectral separation from unlabeled analyte.
• Residual unlabeled analog: Low levels of unlabeled 6‑hydroxynaloxone may bias quantitation; consult the CoA for isotopic distribution (e.g., %D0, %D1, %D2…).
• Counterion/form: Reference standards may be supplied as free base or as a salt (e.g., HCl). The form influences solubility and exact formula/MW; check the CoA.
• Trace-level attributes: Water content, residual solvents, and related substances (desalkylation/oxidation products) are often controlled; for this item they are Not specified; refer to CoA/Spec Sheet.
• Intended use: Provided for research use only; not intended for human or veterinary use, diagnostic procedures, or household use.

Documentation you should expect for rigorous workflows:

• CoA with batch-specific purity, isotopic enrichment, and identity data (NMR, MS, HPLC).
• Guidance on suitable dissolution solvents and recommended storage temperatures.
• Stability statement or re-test date for the batch.

Reaction and Applications

Primary application domain: isotopically labeled internal standard (ILIS) for quantitative LC–MS/MS of 6‑hydroxynaloxone and related metabolites in research matrices (plasma, tissue homogenates, microsomes). This section expands on common analytical workflows rather than synthetic reactions, which are not the principal use for this item.

Analytical applications (general/literature-based):

• Internal standardization: corrects for extraction recovery variability, ion suppression/enhancement, and instrument drift in targeted assays of naloxone metabolites.
• Metabolic studies: tracking formation/clearance of 6‑hydroxylated species in in vitro systems (hepatocytes, liver microsomes, S9), enabling kinetic parameter estimation (e.g., intrinsic clearance) when coupled to appropriate calibration.
• Stability studies: assess analyte stability in biological matrices (bench‑top, freeze–thaw) using ILIS to control for processing artifacts.
• Method validation: used in linearity, accuracy, precision, matrix effect, and carryover assessments per common regulatory guidance for bioanalytical methods (research context).

Practical tips:

• Spike ILIS early: add to samples before protein precipitation or SPE to normalize losses.
• Isotopic distance: ensure sufficient mass shift from native analyte to avoid overlap of isotopic envelopes; confirm absence of D/H exchange under your conditions.
• Chromatography: phenolic/amine functionality typically benefits from acidic mobile phases (e.g., 0.1% formic acid) and reversed-phase columns with embedded polar groups or phenyl phases for better retention/selectivity.

Note: No manufacturer-provided synthetic or catalytic reaction use cases for this item.

Reaction Conditions

No manufacturer reaction conditions are provided, and this item is primarily intended as an LC–MS/MS internal standard rather than a synthetic reagent. The following guidance pertains to analytical handling and is literature/practice-based, not product specifications.

Typical preparation for LC–MS/MS:

• Stock solutions: 0.1–1.0 mg/mL in methanol, acetonitrile, or DMSO. Vortex until fully dissolved.
• Working solutions: dilute stocks with water containing 0.1% formic acid or 5–10 mM ammonium formate/acetate, often 10–50% organic co-solvent.
• Spiking: add internal standard to samples prior to extraction (protein precipitation or SPE) at a constant concentration suitable for the assay dynamic range.

Chromatography and MS (general):

• Columns: C18, phenyl‑hexyl, or polar‑embedded RP phases can improve retention of phenolic/amine analytes.
• Mobile phase: acidic conditions (e.g., 0.1% formic acid) typically enhance ESI+ response for protonated molecules; consider ammonium buffers for volatility.
• Temperatures: ambient to 40 °C to improve peak shape and reproducibility.
• Injection solvent: match to initial mobile phase to mitigate peak distortion.

Stability considerations:

• Protect from light and moisture; maintain at −20 °C.
• Minimize freeze–thaw cycles by aliquoting.
• Evaluate short-term stability (autosampler at 4–10 °C) as part of method validation in your lab.

Safety and Handling

GHS/SDS details are not provided in the product data. Always review the SDS before use.

Item-specific hazard data:

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

General safety considerations for small-molecule opioid-receptor ligands and analytical standards (general guidance):

• Avoid inhalation, ingestion, and skin contact; handle in a certified chemical fume hood or ventilated enclosure, especially when weighing powders or opening ampules/films.
• PPE: lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Consider double-gloving and dedicated tools to minimize contamination.
• Incompatibilities: strong oxidizers; store away from reactive acids/bases. Keep solutions in compatible, well-closed containers.
• First aid (overview; defer to SDS): move exposed person to fresh air if inhaled; rinse skin with water for 15 minutes if contacted; flush eyes with water for at least 15 minutes; if swallowed, rinse mouth—seek medical attention in all cases.
• Spill response: absorb small spills with inert material while minimizing dust/aerosol; dispose in accordance with institutional hazardous waste procedures.
• Environmental: prevent release to drains; collect waste and contaminated disposables in labeled containers.

Special handling:

• Use single-use aliquots for standards to reduce handling frequency.
• Deuterated reference standards should be protected from light and moisture to preserve isotopic integrity.

Solvent Selection

As an isotopically labeled small-molecule standard with a protonatable tertiary amine and phenolic OH, 6‑Hydroxynaloxone‑d dissolves well in polar organic solvents. When preparing stock solutions for LC–MS/MS, solvent choice impacts stability, ionization efficiency, and adsorption losses.

General solvent compatibility and selection (literature/practice-based):

• Strong solvents for stocks (typical): methanol, acetonitrile, DMSO. All three generally provide rapid dissolution at 0.1–10 mg/mL. DMSO maximizes solubility but may be less MS-friendly at higher percentages.
• Working diluents: water with 0.1% formic acid or 5–20 mM ammonium formate/acetate, often with 10–50% MeOH or ACN to mitigate adsorption and improve chromatographic behavior.
• Aqueous buffers: protonate the amine to enhance solubility; avoid high pH (>9) to limit base-catalyzed degradation of phenolic structures.
• Adsorption control: add small amounts of organic modifier (e.g., 5–20% MeOH) or 0.1 mg/mL BSA when working at sub‑ng/mL levels in polypropylene; glass silanization can reduce surface loss (general analytical practice).

Comparison notes:

• Methanol: good solubility, favorable ESI response, greener than ACN.
• Acetonitrile: strong protein precipitation performance for plasma prep; excellent LC eluent strength but higher environmental/handling burden than MeOH.
• DMSO: useful for concentrated stocks and freezer stability; keep final DMSO ≤1–2% in LC–MS to maintain spray stability.

Always filter mobile phases (0.2 µm) and use LC–MS grade solvents to minimize background.

Storage and Reconstitution

Item-specific storage and shipping conditions from Product Data:

• Storage: Store at −20 °C.
• Shipped in: Ice chest + ice pads.

Additional best practices (general guidance; not specifications):

• Protect from light and moisture; keep containers tightly closed under inert headspace if possible.
• After first opening, promptly prepare single-use aliquots of stock solutions to avoid repeated freeze–thaw cycles.
• Preferred solvents for reconstitution: methanol or acetonitrile for concentrated stocks; dilute into aqueous, volatile buffers (e.g., 0.1% formic acid or 5–10 mM ammonium formate/acetate) for working solutions compatible with LC–MS.
• Solution stability: verify short‑ and long‑term stability under your conditions (bench‑top, autosampler at 4–10 °C, and frozen at −20 °C). Include freeze–thaw stability in your method validation.
• Container selection: use amber glass vials with PTFE-lined caps to minimize adsorption and permeation; for very low concentrations, consider low‑bind plastics and addition of minimal organic modifier to reduce surface loss.

Disposal: discard unused materials and solutions according to institutional hazardous chemical waste protocols. This product is for research use only.

Structure and Identity

Item-specific identifiers provided for this listing are limited. Where not provided, consult the CoA/Spec Sheet for definitive identity data.

• Compound type: deuterium-labeled small-molecule; phenolic, tertiary-amine morphinan framework consistent with 6-hydroxylated naloxone analogs (general chemistry/literature description)
• Deuteration: “-d” indicates one or more deuterium atoms incorporated for use as an isotopically labeled internal standard in bioanalytical assays (general)
• 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.
• CAS: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general, based on 6-hydroxynaloxone chemotype):

• Tetracyclic morphinan core with a bridgehead tertiary amine and an allyl N-substituent typical of naloxone-like antagonists
• Phenolic 3‑OH and an additional 6‑OH (increases polarity versus naloxone); one or more deuterium atoms located at specified positions depending on isotopic design (location not specified for this item)
• Contains an aryl ether/phenol, tertiary amine (protonatable), and allylic/olefinic functionality (literature description)

2D structural description (general): a fused tricyclic phenanthrene-like aromatic/partially saturated system bearing a phenolic OH on the A‑ring, bridged to a saturated nitrogen-containing ring (morphinan), with an allyl group on nitrogen and a hydroxyl at C‑6. Exact isotopic labeling pattern is not specified for this item.

Synthetic Utility

While the principal utility of 6‑Hydroxynaloxone‑d is as an isotopically labeled analytical standard, limited synthetic considerations can be noted for the general chemotype.

General considerations (literature/chemotype-based):

• Functional group handles: phenolic OH (can undergo O‑alkylation/acylation under mild conditions), tertiary amine (salt formation, quaternization), and allylic moiety (selective hydrogenation/functionalization). Deuterium incorporation sites are typically selected to resist exchange under analytical conditions; avoid strongly acidic/basic conditions that could promote H/D exchange, especially at heteroatom-adjacent carbons.
• Protection strategies: for derivatization or immobilization studies, transient protection of the phenol (e.g., benzyl, silyl) and amine (e.g., Boc) can be employed; ensure deprotection does not induce H/D scrambling.
• Conjugation chemistry: phenolic coupling to activated carbonates or carbodiimide-mediated linkers enables tag attachment for mechanistic probes; however, such transformations are outside the typical use of a quantified reference standard.

Caution: If using the material in chemical transformations, confirm isotopic location by NMR/MS post-reaction, as some conditions can cause partial deuterium loss. No manufacturer-provided synthetic application data are available for this item.

Target Specificity

Not applicable. This product is a small-molecule standard and not a biological macromolecule or antibody. No antigen/epitope, clone, isotype, or species reactivity information applies.

If studying receptor interactions, consult primary literature for opioid receptor binding characteristics of 6‑hydroxylated naloxone analogs. Such data are not provided for this item.

Frequently Asked Questions

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is H1440413, the molecular formula is C19H20D3NO4, and the molecular weight is 332.41 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.