Moexipril-d , CAS No.1356929-49-1

CAS: 1356929-49-1 Cat. No.: M1416725 Formula: C₂₇H₂₉D₅N₂O₇ Molecular Weight: 503.6 PubChem CID: 45039952

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Moexipril-d 5 is the deuterium labeled Moexipril. Moexipril hydrochloride is a potent orally active non-sulfhydryl angiotensin converting enzyme (ACE) inhibitor, which is used for the treatment of hypertension and congestive heart failure.

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

• Canonical Smiles: CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CC3=CC(=C(C=C3CC2C(=O)O)OC)OC
• IUPAC Name: (3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-(2,3,4,5,6-pentadeuteriophenyl)butan-2-yl]amino]propanoyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
• InChIKey: UWWDHYUMIORJTA-SBCWFVTISA-N
• INCHI: 1S/C27H34N2O7/c1-5-36-27(33)21(12-11-18-9-7-6-8-10-18)28-17(2)25(30)29-16-20-15-24(35-4)23(34-3)14-19(20)13-22(29)26(31)32/h6-10,14-15,17,21-22,28H,5,11-13,16H2,1-4H3,(H,31,32)/t17-,21-,22-/m0/s1/i6D,7D,8D,9D,10D
• Isomeric SMILES: [2H]C1=C(C(=C(C(=C1[2H])[2H])CC[C@@H](C(=O)OCC)N[C@@H](C)C(=O)N2CC3=CC(=C(C=C3C[C@H]2C(=O)O)OC)OC)[2H])[2H]
• PubChem CID: 45039952
• Molecular Weight: 503.6

Application Protocols

No assay-specific, item-validated protocols are provided in the Product Data. The following is general guidance for LC–MS internal standard use; adjust to your method and instrumentation.

• Stock preparation:
  • Weigh accurately in a dry environment. Prepare a 1–10 mg/mL stock in DMSO or MeOH. Record exact concentration and date.
• Working solutions:
  • Dilute stock into MeOH/H2O or MeCN/H2O with 0.1% formic acid or 5–10 mM ammonium formate/acetate. Keep final organic content ≥10% to prevent precipitation.
• Spiking:
  • Add a fixed concentration of Moexipril-d to all calibrators, QCs, and study samples prior to extraction to correct for recovery and matrix effects (isotope-dilution principle).
• LC–MS/MS acquisition:
  • Optimize MRM transitions based on the item’s isotopic mass shift (consult CoA for D count/positions). Verify minimal cross-talk with the analyte channel.
• Stability:
  • Assess bench-top, autosampler (4–10 °C), freeze–thaw, and long-term storage stability as part of method validation.

Note: Exact dilution factors, injection volumes, and transitions are method-dependent and should be empirically optimized.

Biological Roles

General, literature-based background (not item-specific):

• Moexipril is a prodrug that, upon hydrolysis to moexiprilat, inhibits angiotensin-converting enzyme (ACE) by chelating the active-site Zn2+ and blocking the conversion of angiotensin I to angiotensin II. This is a biochemical mechanism description and not a therapeutic claim.
• Structural pharmacophore: a proline-derived scaffold with a secondary amine and diacid motif (in the active form) enables binding to the ACE catalytic pocket.
• Metabolism: prodrug ester hydrolysis (carboxylesterases) generates the active diacid; additional Phase I/II metabolism (e.g., oxidation, conjugation) may occur depending on species and conditions.
• Deuterated analogs like Moexipril-d are used as biochemical probes or internal standards to trace absorption, distribution, metabolism, and excretion (ADME) pathways without altering target engagement significantly.

Use limitations and scope

• This product is designated for research use only. It is not intended for human or animal administration, diagnostic, or clinical purposes.
• When used in cell or tissue studies, ensure vehicle controls and assess potential solvent effects (e.g., DMSO at ≤0.1–0.5% v/v to limit cytotoxicity), recognizing that the prodrug’s intracellular hydrolysis may vary by system.

Buffer Applications

This small-molecule reference standard is not itself a buffering agent and is not used to establish pH. Brief, practical notes for analytical workflows:

• For LC–MS, volatile aqueous buffers (e.g., ammonium formate or ammonium acetate, pH 3–6) are commonly employed to improve peak shape and ionization of analytes like moexipril.
• Avoid highly basic buffers if ester stability is a concern; base can accelerate hydrolysis to moexiprilat.
• Maintain consistent buffer ionic strength and pH across calibrators and samples when performing isotope-dilution quantitation with Moexipril-d.

No standard buffer recipes are provided for this compound; select buffer systems based on your chromatographic method and analyte stability.

Green Alternatives

For preparation of stocks and LC–MS workflows with Moexipril-d, solvent choices drive the environmental profile.

Greener solvent considerations (general):

• Prefer methanol over acetonitrile where performance allows; MeOH is renewable-derived and has lower life-cycle impact in many assessments.
• Use water-rich mobile phases with volatile buffers (formate/acetate) to reduce organic solvent consumption.
• Minimize DMSO volumes to what is necessary for solubilization; although low-toxicity, it can complicate aqueous waste streams.

Comparison (general guidance)

• Parameter | MeOH | MeCN | DMSO
• ----------|------|------|-----
• EHS profile | Lower toxicity, biodegradable (relative) | Toxicity/HCN risk in synthesis, higher environmental burden | Low volatility, low flammability; difficult to remove
• MS compatibility | Excellent (ESI-friendly) | Excellent | Good at low %; can suppress at high %
• Evaporation | Easy | Very easy | Difficult
• Green preference | Often preferred | Use when necessary | Limit use

Operational practices

• Scale down calibration series and use automated diluters to reduce solvent volumes.
• Implement closed-waste collection for organic solvents and segregate halogen-free streams for optimized disposal.
• Consider on-instrument mixing (bi-solvent pumps) to cut solvent prep waste.

Pharmaceutical Uses

No therapeutic or clinical use is claimed for this catalog item. Guidance below pertains to research, analytical, and manufacturing control contexts only.

• Analytical reference standard: Moexipril-d can serve as an internal standard in pharmaceutical quality control assays (e.g., assay/potency, related substances, stability-indicating HPLC–MS) for drug substance or finished product testing of moexipril-containing materials.
• Process development support: Use during formulation or process stress studies to differentiate analyte responses from matrix effects owing to excipients and to correct for extraction recoveries in sample-prep validation.
• Regulatory documentation: Deuterated internal standards are commonly cited in method validation reports (e.g., specificity/selectivity, accuracy, precision). Ensure retention of CoA, isotopic enrichment documentation, and storage records.

Pharmacopeial status, excipient roles, and compendial references are not specified for this item; consult current pharmacopeias and your quality unit if required.

Physical Properties

Item-specific properties (from Product Data)

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

Thermophysical/chemical data

• Melting point (literature, parent moexipril or salts): values vary with salt form; solid-state data are formulation-dependent. Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable for typical solid API analogs; decomposition may occur before boiling. Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• LogP/logD (literature, parent): prodrug esters are moderately lipophilic relative to active diacids; exact value depends on ionization state. Not specified for this item; refer to CoA/Spec Sheet.
• pKa (literature, parent): multiple ionizable groups (carboxylate and secondary amine) lead to amphoteric behavior; precise values vary by form. Not specified for this item; refer to CoA/Spec Sheet.
• Solubility profile (general guidance):
  • Often sparingly soluble in water at neutral pH (prodrug ester); solubility increases in polar aprotic solvents (e.g., DMSO) and in aqueous buffers when ionized (salts, higher pH).
  • For LC–MS stock solutions, DMSO or MeOH are commonly used, followed by dilution into aqueous mobile phases.
• Optical rotation/refractive index: Not applicable/Not specified for this item; refer to CoA/Spec Sheet.

Note: Because this is a deuterated analog, most bulk physical constants closely track the non-deuterated compound, with small mass-dependent shifts (literature).

Quality and Grades

Item-specific quality information (from Product Data)

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

Guidance on deuterated reference standards (general)

• Deuterated small molecules such as Moexipril-d are commonly supplied as analytical reference materials for LC–MS/GC–MS quantification, offering a defined mass shift relative to the non-deuterated analyte and closely matched chromatographic behavior.
• Typical quality attributes for such materials include: high chemical purity, defined isotopic enrichment and labeling pattern, and low levels of residual solvents/inorganics. These parameters, along with identity confirmation (NMR, HRMS), are specified on the CoA.
• Stabilizers: Not specified for this item. If present, stabilizers will be declared on the CoA; their presence can influence UV detection/background and should be factored into method validation.
• Documentation: For regulated bioanalytical workflows, retain CoA and, if available, isotopic distribution data and impurity profiles to support method validation (selectivity/matrix effects).

If your application requires particular specifications (e.g., minimum isotopic enrichment, residual solvent limits, salt form), please confirm against the item’s CoA/Specification Sheet prior to use.

Reaction and Applications

This product is primarily intended as a deuterated analytical standard rather than a synthetic reagent. Typical research applications include:

• LC–MS/LC–MS/MS internal standard for quantitation of moexipril in pharmacokinetic, metabolism, or stability studies. The deuterium label provides a consistent mass offset, minimizing matrix effects due to coelution with the analyte.
• Metabolic mapping: comparison of fragmentation pathways between moexipril and Moexipril-d can reveal sites of biotransformation (literature), aiding in metabolite identification strategies.
• Isotope-dilution assays: enables absolute quantitation with high accuracy/precision when spiked at a fixed concentration across calibrators and samples.
• Stability-indicating methods: track degradation (e.g., ester hydrolysis to moexiprilat) using Moexipril-d as a process/control standard.

Practical tips

• Confirm the labeling pattern and isotopic enrichment from the CoA to select appropriate SRM/MRM transitions (avoid channels with H/D exchange susceptibility).
• For ESI–MS, monitor both protonated molecular ion and key product ions; validate that the deuterium label remains intact under source/fragmentation conditions.
• Avoid protic/acidic conditions that can promote H/D back-exchange at exchangeable positions (if applicable to the specific labeling sites).

Note: If you intend to use this compound in chemical reactions, treat it like the non-deuterated prodrug ester—sensitive to hydrolysis and aminolysis—while recognizing that kinetic isotope effects are usually minor for non-exchangeable D labels.

Reaction Conditions

As an analytical standard, Moexipril-d is typically not subjected to preparative reactions. General, literature-based conditions related to the chemotype are provided for method-development and stability studies:

• Hydrolysis (ester to diacid): Aqueous base (e.g., NaOH, pH > 10) or enzymatic (esterases) at ambient to 40 °C accelerates conversion to the active diacid; acid-catalyzed hydrolysis proceeds more slowly but is possible under strong acids. Monitor by LC–MS/MS.
• Salt formation: Dissolve in minimal alcohol or acetone and treat with mineral or organic acids to obtain hydrochloride or other salts; conditions vary with counterion and solvent.
• Stability studies: Conduct stress testing per ICH-like paradigms (acid/base, oxidative, thermal, photolytic). Use Moexipril-d as an internal or system-suitability standard to track recovery and matrix effects.
• Chromatography: Reversed-phase C18 with aqueous formate/acetate buffers (pH 3–5) and MeOH/MeCN gradients commonly resolve prodrug and diacid forms. Validate that the deuterium label does not alter retention factors significantly at your gradient and pH.

Expected yields, rates, or exact kinetic parameters are not specified for this item; consult the literature for parent-compound studies if needed.

Safety and Handling

GHS and hazard information (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 (good practice; defer to SDS for authoritative guidance)

• Handle in a well-ventilated fume hood, minimizing dust/aerosol generation.
• Recommended PPE: lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Avoid skin/eye contact and inhalation of particulates.
• Incompatibilities: strong oxidizers and strong acids/bases may effect degradation or hydrolysis of ester/amide functionalities (general for this chemotype). Avoid moisture for accurate weighing and to prevent hydrolysis of prodrug esters.
• First aid (overview):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical evaluation as needed.
  • Ingestion: rinse mouth; do not induce vomiting unless directed by medical personnel.
• Spill response: avoid raising dust; collect using damp disposable towels or HEPA-filtered vacuum; dispose per institutional and local regulations.
• Fire safety: use CO2, dry chemical, or foam. Combustion may generate COx and nitrogen-containing vapors; firefighters should wear SCBA.

Always consult the product-specific SDS for definitive hazard classification, exposure limits, and disposal instructions.

Solvent Selection

Moexipril-d, as a deuterated prodrug analog, is typically handled as a solid reference material for LC–MS.

• Primary stock solvents (practice-based guidance):
  • DMSO: excellent solvency and chemical stability; compatible with LC–MS after dilution. Common for 1–10 mg/mL stocks.
  • Methanol (MeOH) or Acetonitrile (MeCN): suitable for LC–MS standards; may be preferable for direct spiking into aqueous mobile phases.
  • Water/buffer: solubility often limited at neutral pH for the prodrug ester; salt forms or adjusted pH may improve solubility (item-specific behavior not specified).
• Miscibility and dilution: Prepare concentrated stocks in DMSO/MeOH, then dilute into aqueous mobile phase containing volatile buffers (e.g., formate/acetate) to minimize precipitation. Keep final organic fraction ≥10–20% during dilution to prevent out-of-solution losses.
• Adsorption and carryover: Use low-bind plastics or silanized glass for low-concentration standards; pre-rinse vials with working solvent to minimize adsorption to surfaces.

Small comparison (general)

• DMSO vs MeOH:
  • DMSO: higher solvency, better for long-term concentrated stocks; may suppress ESI at high %.
  • MeOH: volatile, MS-friendly; slightly lower solvency; ideal for calibration working solutions.
• MeCN: strong eluent strength in reversed-phase LC; rapid evaporation; good for short-term standards.

Storage and Reconstitution

Item-specific storage/shipping (from Product Data)

• Storage conditions: Store at -20°C.
• Shipped in: Ice chest + Ice pads.

Handling and stability guidance

• Upon receipt, allow the sealed container to equilibrate to room temperature before opening to prevent moisture condensation. Reseal promptly under dry air or inert gas with desiccant if available.
• For long-term storage, keep tightly capped, protected from light and moisture. Divide into single-use aliquots to avoid repeated freeze–thaw and adsorption losses at low concentrations.
• Reconstitution: Prepare concentrated stock solutions in DMSO or methanol; filter if needed through a 0.2 µm PTFE syringe filter. Record solvent, date, and calculated concentration on the vial.
• Solution storage: Store aliquots at -20°C (or per your method validation) in amber vials. Avoid extended storage in aqueous media to limit hydrolysis of ester functionalities. Verify concentration periodically by LC–MS using response factors.

Shelf-life and exact stability parameters are not specified for this item; refer to the CoA/SDS and confirm suitability in your specific application.

Structure and Identity

Item-specific identifiers (from Product Data)

• Product name: Moexipril-d (deuterated moexipril; exact labeling positions not specified)
• SKU: M1416725
• CAS: 1356929-49-1
• PubChem CID: 45039952
• InChIKey: 371240 (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.

General structural notes (literature, for context only — not item-specific)

• Moexipril is a prodrug angiotensin-converting enzyme (ACE) inhibitor structurally related to diacidic proline-derived inhibitors. It typically contains: an ester prodrug moiety (hydrolyzable), a secondary amine, and two carboxylate equivalents in the active form (moexiprilat).
• The “-d” suffix denotes incorporation of one or more deuterium (²H, D) atoms; common practice is placement at metabolically labile C–H positions to create a mass shift for LC–MS quantitation. Exact number and positions of D are not specified for this item.
• 2D depiction (literature, descriptive): a bicyclic proline-like core joined via an amide/secondary amine linkage to a substituted aliphatic chain bearing an ethyl ester; multiple stereocenters are present in the parent drug. Stereochemistry and deuterium placement for this catalog item are not specified.

Synthetic Utility

While supplied primarily as a deuterated analytical standard, the underlying chemotype offers insights for synthetic chemists (general, literature-based):

• Functional groups: secondary amine, amide/peptidic linkage, and an ester prodrug moiety; these enable transformations such as hydrolysis to the active diacid, salt formation, or coupling at the amine.
• Label retention: If deuterium is installed at non-exchangeable aliphatic positions, it generally persists through neutral and mildly acidic/basic manipulations; exchange-prone sites (O–D, N–D, α-heteroatom) may scramble under protic or strongly basic conditions.
• Retrosynthetic elements: moexipril scaffolds are accessible by coupling a protected proline-derived bicyclic fragment with a suitably functionalized side chain, followed by esterification and deprotection steps; deuterium can be introduced via labeled building blocks or reduction/hydrogenation with D2/deuterated hydrides.
• Applications: use as a tracer in reaction monitoring (e.g., track selective hydrolysis or aminolysis) to quantify conversion and discriminate product/impurity pathways by MS.

Note: If synthetic modification is intended, verify the exact D-labeling positions from the CoA to avoid undesired label loss or migration during the planned steps.

Target Specificity

This product is a small-molecule reference standard and not a biological macromolecule or antibody. Therefore, parameters such as antigen/epitope, species reactivity, clone, and isotype are not applicable.

For biochemical context (literature, non-item-specific): the parent active form (moexiprilat) binds the zinc-dependent catalytic site of ACE. However, no target-binding specifications are provided or claimed for this item.