Ritodrine HCl - 10mM in DMSO , CAS No.23239-51-2

CAS: 23239-51-2 Cat. No.: R408588 Formula: C₁₇H₂₁NO₃·HCl Peso molecolare: 323.81 Numero EC: 245-514-8 PubChem CID: 31728

GRADE & PURITY 10mM in DMSO

Synonyms

NSC 291565 | (αS)​-​rel-4-​hydroxy-​α-​[(1R)​-​1-​[[2-​(4-​hydroxyphenyl)​ethyl]​amino]​ethyl]​-benzenemethanol, hydrochloride (1:1)

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Panoramica

Information

Ritodrine HCl (NSC 291565) is a hydrochloride salt of ritodrine which is a β-2 adrenergic receptor agonist.
In vitro

In vivo

Cell Data

cell lines：

Concentrations：

Incubation Time：

Powder Purity:≥99%

Specifications

Sinonimi

NSC 291565 | (αS)​-​rel-4-​hydroxy-​α-​[(1R)​-​1-​[[2-​(4-​hydroxyphenyl)​ethyl]​amino]​ethyl]​-benzenemethanol, hydrochloride (1:1)

Specifiche e purezza

10mM in DMSO

Meccanismi biochimici e fisiologici

Ritodrine HCl (NSC 291565) is a hydrochloride salt of ritodrine which is a β-2 adrenergic receptor agonist.

Condizioni di conservazione di stoccaggio

Store at -80°C

Spedito in

Dry ice packs + Cold packs

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Nomi e identificatori

Isomeri SMILES

C[C@@H]([C@@H](C1=CC=C(C=C1)O)O)NCCC2=CC=C(C=C2)O.Cl

WGK Germania

3

RTECS

DO6524000

CAS alternativo

26652-09-5

PubChem CID

31728

Peso molecolare

323.81

Reaxy-Rn

5321399

Proprietà chimiche e fisiche

• Solubilità: Solubility (25°C) In vitro DMSO: 33 mg/mL (199.72 mM); Ethanol: 33 mg/mL (199.72 mM); Water: Insoluble
• Punto di fusione (°C): 195°C(dec.)(lit.)

Application Protocols

No manufacturer-validated application protocols are provided for this SKU. The following are example research workflows (literature, general) to guide in-house method development. Adjust to your system.

1. cAMP accumulation assay (cell-based):

• Prepare a 10 mM DMSO stock; serially dilute in assay buffer to 0.1 nM–10 µM.
• Plate ADRB2-expressing cells, equilibrate in HBSS/HEPES with 0.5 mM IBMX.
• Add ligand dilutions, incubate 10–30 min at 37°C.
• Quantify cAMP via HTRF/EIA per kit instructions. Analyze EC50 and Emax.

2. Radioligand binding (membrane prep):

• Use [3H]-dihydroalprenolol or other β-AR radioligand.
• Incubate membranes with fixed radioligand and varying unlabeled ligand concentrations for 60 min at 25°C in Tris/Mg2+ buffer.
• Separate bound/free via rapid filtration; count radioactivity to generate competition curves (Ki by Cheng–Prusoff).

3. LC–MS calibration curve (analytical):

• Prepare standards 1–1000 ng/mL in 0.1% formic acid in water/MeOH (80:20).
• Inject onto C18 column; mobile phase water/MeOH with 0.1% formic acid; monitor [M+H]+.
• Evaluate linearity (R2), LOD/LOQ, precision, and recovery in matrix.

Note: These are non-validated examples for research only. Optimize parameters for your instruments and biosystems.

Biological Roles

Ritodrine (as hydrochloride) is an arylethanolamine ligand used as a research tool to probe adrenergic receptor biology (literature, general). The following information is provided for biochemical context only.

• Primary molecular target: β-adrenergic receptors, with reported preference toward the β2-adrenergic receptor (ADRB2) class in literature for related structures.
• Mechanistic theme: Agonist binding stabilizes active receptor conformations, typically leading to Gs protein coupling, adenylyl cyclase activation, and cAMP accumulation. Downstream signaling can include PKA activation and modulation of Ca2+ handling in excitable and smooth muscle cells (research context).
• Structure–activity relationships (SAR): β-agonist activity depends on the β-amino alcohol motif, aromatic substitution pattern, and amine substituents that tune β2 selectivity (literature, class-level SAR).
• Transport/metabolism: Cationic amines may interact with organic cation transporters (OCTs); phenolic/catecholic groups, if present, can undergo phase II conjugation (sulfation/glucuronidation) in biological systems (literature, general). Actual pathways should be confirmed experimentally for this compound.
• Experimental uses: benchmarking receptor activation, studying desensitization/internalization of ADRB2, and characterizing downstream cAMP/PKA signaling cascades in cell lines or tissue preparations.

Note: No medical or clinical claims are made. Use strictly for research applications under appropriate institutional approvals.

Buffer Applications

While Ritodrine HCl is not a buffer component, its ionization state and stability are influenced by buffer conditions—important for reproducible assays.

• pH considerations (literature, general): Secondary amines in arylethanolamines are protonated under acidic to neutral conditions (pH < ~9), maximizing aqueous solubility. Work near pH 5.5–7.4 for biological assays to balance solubility and physiological relevance.
• Common buffers: phosphate-buffered saline (PBS), HEPES, or Tris can be used. Avoid high-pH Tris (>8.5) if degradation is observed. Include 0.1% carrier protein (e.g., BSA) only if compatible with readouts to minimize adsorption at very low concentrations.
• Stock preparation: Prepare concentrated stocks in water (with 0.1% formic or acetic acid if needed) or DMSO, then dilute into buffer. Filter 0.2 µm if particulate forms.
• Ionic strength: Elevated ionic strength can affect receptor binding kinetics and LC retention; keep salt concentration consistent across experiments.
• Analytical buffers (LC–MS): Use volatile systems (e.g., 5–20 mM ammonium formate/acetate, 0.1% formic acid) for positive ESI. Control pH to maintain the protonated form for robust ionization.

Item-specific buffer compatibility and pH stability: Not specified for this item; refer to CoA/Spec Sheet and perform pilot stability checks.

Green Alternatives

As a defined bioactive analyte rather than a process solvent or reagent, "green alternatives" focuses on solvent and workflow choices to reduce environmental impact while preserving data quality.

Greener handling choices (general):

• Prefer water or buffered aqueous media for working solutions whenever compatible with your assay.
• If high-concentration stocks are required, DMSO is typically favored over DMF or NMP for toxicity and handling reasons.
• Minimize organic solvent volumes during method development; adopt micro-scale assays and 96/384-well formats to reduce waste.
• For chromatography, use UPLC with smaller columns and lower flow rates; consider ethanol or methanol in place of acetonitrile when method performance allows.

Comparison (literature, general):

• DMSO vs DMF/NMP: lower chronic toxicity and better biodegradation profile; broad solubilizing power for salts.
• Aqueous buffers vs neat organics: reduced VOC emissions; may require pH control to keep the amine protonated and soluble.

Trade-offs:

• Replacing ACN with MeOH can change selectivity and increase backpressure; method re-optimization is required.
• Aqueous systems can promote hydrolysis/oxidation; employ antioxidants, deoxygenation, or low-temperature storage as needed.

Conclusion: Optimize solvent systems toward water-rich media and DMSO stocks, scale down experiments, and implement modern LC methods to improve sustainability without altering the compound itself.

Pharmaceutical Uses

This product is supplied strictly for research use. No medical or clinical use is intended or implied.

Relevant to formulation science and quality control (non-clinical, literature/general):

• Reference standard: may be employed as a system suitability or calibration standard in analytical methods that quantify arylethanolamine β-agonists in research samples.
• Salt selection insights: The hydrochloride counterion is commonly chosen to enhance aqueous solubility and crystallinity of amine-containing APIs; researchers can compare salt forms to study physicochemical properties without implying therapeutic use.
• Preformulation studies: solubility profiling across pH, hygroscopicity assessment, and solid-state characterization (XRPD/DSC/TGA) can be conducted for material science understanding.
• Impurity profiling: forced degradation under oxidative, thermal, and photolytic conditions to elucidate degradation pathways; develop stability-indicating methods.

Regulatory/compendial status specific to this SKU: Not specified for this item; refer to CoA/Spec Sheet and applicable pharmacopeial resources if needed for method transfer or cross-reference as a research standard.

Physical Properties

Only item-specific figures that appear on the CoA/Spec Sheet should be used for specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (MW): Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (salts of arylethanolamines typically show well-defined MPs; literature values vary by crystal form)
• Boiling point: Not applicable to the salt in practice (decomposes); Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility:
  • Water: high aqueous solubility is typical for hydrochloride salts of arylethanolamines (literature, qualitative). Exact solubility: Not specified for this item; refer to CoA/Spec Sheet.
  • DMSO: generally soluble (literature, qualitative). Exact solubility: Not specified for this item; refer to CoA/Spec Sheet.
  • Alcohols/buffers: often soluble depending on pH and ionic strength (literature, qualitative).
• pKa (amine): arylethanolamine secondary amines typically pKa ~9–10 (literature, general); exact value for this item: Not specified.
• LogP/LogD: cationic at physiological pH leading to low LogD7.4 (literature, qualitative); specific values for this item: Not specified.
• Refractive index/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Notes (general): As a protonated hydrochloride, the compound is hygroscopic tendencies may be formulation-dependent; confirm handling characteristics on receipt.

Quality and Grades

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

Context for small-molecule bioactives (general guidance):

• Research/analytical grade materials are typically qualified by NMR/LC–MS/HRMS and chromatographic purity (e.g., HPLC area %). For receptor pharmacology and cell studies, low-level inorganic/organic impurities and residual solvents can confound bioassays; consult the CoA for purity metrics and impurity thresholds.
• Salt content and counterion equivalence: For hydrochloride salts, assay content is often reported as % on anhydrous basis and may include residual water and counterion content; these affect molar calculations. If not specified, determine assay by quantitative NMR or titration.
• Stabilizers: No stabilizers are listed in Product Data. If present, stabilizers or water of crystallization would be declared on the CoA; absence here does not imply absence—verify on documentation.
• UV/fluorescence background: For analytical uses (HPLC/UPLC standards), low UV-absorbing impurities and baseline stability are important. If HPLC grade or reference standard grade is required, confirm with Technical Support/CoA.

Bottom line: Use the CoA/Spec Sheet as the authoritative source for purity, salt form confirmation, residual solvent/water, and assay; do not assume values not documented.

Reaction and Applications

This product is primarily a bioactive small molecule standard rather than a synthetic reagent. Accordingly, its most relevant laboratory applications are in analytical and biological assay contexts:

• Reference/Calibration standard: for LC–MS or HPLC method development/validation in matrices relevant to adrenergic ligand analyses (literature, general). Optimize mobile phase pH to maintain protonation and sharp peaks.
• Pharmacology: tool compound for β-adrenergic receptor activation studies (binding assays, functional cAMP readouts) in recombinant or native systems (literature). Avoid therapeutic interpretations; research use only.
• Transport/metabolism studies: substrate in investigations of catecholamine-mimetic metabolism (e.g., COMT/MAO considerations depend on structure; confirm experimentally) and uptake/efflux transporter assays (literature, general).
• Stability studies: evaluate pH- and temperature-dependent degradation kinetics of arylethanolamine salts; support forced-degradation profiling for method robustness.

Practical tips:

• Prepare concentrated DMSO stocks (e.g., 10–50 mM) or aqueous acidic stocks to enhance stability; aliquot to minimize freeze–thaw.
• Protect from light and moisture; catechol/phenolic motifs are susceptible to oxidative darkening—include antioxidant only if compatible and documented for your workflow.
• For LC–MS, use volatile acids (0.1% formic acid) for positive ESI response; monitor for in-source fragments typical of β-amino alcohols.

Note: Not generally used as a coupling partner or reagent in synthetic transformations.

Reaction Conditions

This section provides general laboratory conditions for preparing and using Ritodrine HCl solutions in research assays; it is not a catalog of chemical reactions.

• Stock solutions: Common practice is 10–50 mM in DMSO or 1–10 mg/mL in water with 0.1% acid (formic/acetic) to ensure complete dissolution (literature, general). Item-specific solubility limits are Not specified; confirm experimentally.
• Working concentrations: For receptor assays, working ranges often span nM–µM depending on system sensitivity (literature). Define dynamic range by preliminary titration.
• Temperature: Prepare and store solutions at 2–8°C short-term during the day; for long-term, aliquot and freeze per Storage guidance.
• Light/oxygen: Protect from light and minimize air exposure; consider degassed buffers if oxidative discoloration is observed.
• Materials: Use low-bind plastics or silanized glass for low-concentration work to minimize adsorption; pre-rinse syringes/filters with solution to condition surfaces.
• Analytical detection: Positive-ion ESI-MS typically gives strong response with 0.1% formic acid; monitor single protonated species and characteristic fragments for identity/quantitation.

Note: Numerical “expected yields” and catalyst/temperature parameters for chemical synthesis do not apply here given the compound’s role as a bioactive standard rather than a reagent.

Safety and Handling

Safety data for this specific lot/formulation should be taken from the SDS.

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

General laboratory precautions (good practice):

• PPE: lab coat, nitrile gloves, and safety glasses. Avoid inhalation of dust and contact with skin or eyes. Use in a chemical fume hood when weighing/handling powders or preparing solutions.
• Incompatibilities (general): strong oxidizers; strong bases/acids may alter salt form and stability. Avoid prolonged exposure to elevated temperatures, moisture, and light.
• First aid (overview): in case of skin or eye contact, rinse with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested or in case of any exposure concerns, seek medical attention. Always follow institutional safety protocols.
• Spill/cleanup: avoid dust generation; gently sweep/collect and place in appropriate waste container. Decontaminate surfaces with water/compatible solvent.
• Waste disposal: treat as organic laboratory chemical waste; follow local regulations.

Special note: As a bioactive adrenergic ligand, avoid accidental exposure. Handle minimal quantities and label clearly. Defer to the product SDS for authoritative hazard classification and exposure controls.

Solvent Selection

Ritodrine HCl is a protonated arylethanolamine salt; solvent choice is driven by desired assay conditions and solubility.

• Polarity/miscibility (general):
  • Water: typically freely soluble for HCl salts; suitable for most biochemical assays.
  • DMSO: broadly miscible and commonly used for high-concentration stock solutions for screening.
  • Alcohols (MeOH, EtOH): moderate-to-good solubility expected; may be used for analytical standards.
  • Buffers: soluble in common biological buffers; pH can modulate ionization and solubility.
• Dielectric considerations: As a cationic compound, high-dielectric solvents (water, formamide) and polar aprotic media (DMSO) support dissolution (literature, general).
• When to choose what:
  • Choose water or buffer when organic cosolvents interfere with biology or analytics.
  • Choose DMSO for concentrated master stocks (e.g., 10–50 mM), then dilute into assay buffer keeping final DMSO ≤0.1–1% v/v as tolerated.
  • Choose MeOH/ACN for LC methods or preparing external standards; verify detector response and stability.
• Compatibility notes:
  • Avoid strong base in aqueous media to prevent degradation of β-amino alcohols.
  • Filtration through 0.2 µm PTFE or PES is generally compatible; confirm adsorption losses if working at low µM levels.

Always confirm actual solubility and stability empirically with your lot; item-specific solubility is Not specified for this item; refer to CoA/Spec Sheet.

Storage and Reconstitution

• Storage conditions (as supplied): Store at -80°C (Product Data). Protect from light and moisture. Keep container tightly closed.
• Shipping: Shipped on dry ice packs + cold packs (Product Data) to maintain low temperature and integrity.
• Stability: Item-specific shelf-life and stability data are Not specified for this item; refer to CoA/Spec Sheet. As a general practice for arylethanolamine salts, avoid repeated warming and moisture exposure.

Reconstitution (general guidance for research use):

• Allow vial to equilibrate to room temperature in a desiccated environment before opening to prevent condensation.
• For stock solutions, dissolve in DMSO (e.g., 10–50 mM) or water (optionally acidified with 0.1% formic or acetic acid) to ensure full solubility. Exact solubility for this item is Not specified.
• Filter sterilize (0.2 µm) if sterility is required for cell-based assays.
• Aliquot stocks into single-use volumes; store aliquots at -80°C. Avoid multiple freeze–thaw cycles; thaw on ice and use promptly.
• For short-term working solutions, store at 2–8°C and use within 24–48 h, monitoring for precipitation or discoloration.

Always consult the CoA/SDS for item-specific instructions on storage and handling, and validate solution stability under your laboratory conditions.

Structure and Identity

Ritodrine HCl is a small-molecule bioactive in the phenethylamine/arylethanolamine class supplied as the hydrochloride salt for research use.

• CAS: 23239-51-2 (product-specific)
• PubChem CID: 31728 (literature)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (general literature identifies ritodrine hydrochloride as the protonated salt of a chiral arylethanolamine)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (literature, general):

• Core scaffold: arylethanolamine (phenethylamine) containing a secondary amino alcohol (β-amino alcohol) motif typical of adrenergic ligands.
• Aromatic substituents: substituted phenyl ring bearing phenoxy/alkyl substituents consistent with β2-adrenergic preference.
• Stereochemistry: contains a single chiral center at the β-carbon (the carbon bearing the hydroxyl group). Commercial materials may be racemic unless specified otherwise.
• Salt form: provided as a hydrochloride to enhance aqueous solubility and handling stability.

2D description in words (literature): an aromatic ring connected through a short aliphatic linker to a chiral carbon bearing a hydroxyl group and a side-chain secondary amine; the amine is protonated in the HCl salt.

Synthetic Utility

Ritodrine HCl is a finished bioactive small molecule and is not typically used as a building block. For completeness, the functional groups present suggest potential reactivity in a purely synthetic/academic context (literature, general):

• β-Amino alcohol: can undergo protection (e.g., Boc on amine), oxidation of the alcohol, or intramolecular transformations under activating conditions; however, these are not common uses for a final analyte.
• Aromatic substituents: phenolic groups (if present in the particular structure) are susceptible to ether formation, acylation, or oxidative coupling. Exercise caution to avoid undesired modification during handling.
• Salt form: the hydrochloride facilitates handling but may require basification to access the free base if synthetic derivatization were intended.

Typical use in the lab is as a tool compound/standard, not as a reagent. If synthetic derivatization or metabolite synthesis is desired, it is generally preferable to start from simpler arylethanolamine precursors rather than from the final hydrochloride salt.

Target Specificity

Target information is provided as general literature context for research planning; this SKU’s item-specific bioactivity panel is not provided.

• Primary target class: G protein-coupled receptors (GPCRs), β-adrenergic receptors.
• Selectivity: Literature on related arylethanolamines indicates preferential activity at β2-adrenergic receptors (ADRB2). Exact Ki/EC50 values and β1/β2 selectivity ratios for this item are Not specified; consult primary literature and perform in-house benchmarking.
• Functional readouts: cAMP accumulation assays, CRE-reporter assays, PKA substrate phosphorylation, and smooth muscle tension measurements (organ bath) are typical endpoints in research.
• Off-target considerations: At higher concentrations, adrenergic ligands may interact with other aminergic GPCRs or monoamine transporters (literature, general). Define concentration windows to minimize off-target effects.

Item-specific potency/purity data: Not specified for this item; refer to CoA/Spec Sheet or test under your assay conditions.