Phenyltoloxamine - Moligand™,≥98% , CAS No.92-12-6

CAS: 92-12-6 Cat. No.: P1369338 Fórmula: C₁₇H₂₁NO Peso molecular: 255.35 Número CE: 202-127-9

GRADE & PURITY Moligand™, ≥98%

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Specifications

Especificações e pureza

Moligand™,≥98%

Condições de armazenamento de armazenamento

Store at -20°C,Argon charged

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Grau

Moligand™

Tipo de ação

INHIBITOR

Pureza

≥98%

Nomes e identificadores

Sorrisos canónicos

CN(C)CCOC1=CC=CC=C1CC2=CC=CC=C2

IUPAC Name

2-(2-benzylphenoxy)-N,N-dimethylethanamine

InChIKey

IZRPKIZLIFYYKR-UHFFFAOYSA-N

INCHI

1S/C17H21NO/c1-18(2)12-13-19-17-11-7-6-10-16(17)14-15-8-4-3-5-9-15/h3-11H,12-14H2,1-2H3

Peso molecular

255.35

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Diphenylmethanes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Diphenylmethanes
• Intermediate Tree Nodes: Not available
• Direct Parent: Diphenylmethanes
• Alternative Parents: Phenoxy compounds Phenol ethers Alkyl aryl ethers Trialkylamines Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Diphenylmethane - Phenoxy compound - Phenol ether - Alkyl aryl ether - Tertiary aliphatic amine - Tertiary amine - Ether - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Amine - Aromatic homomonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propriedades químicas e físicas

• Peso molecular: 255.350 g/mol
• XLogP3: 3.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 255.162 Da
• Monoisotopic Mass: 255.162 Da
• Topological Polar Surface Area: 12.500 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 235.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No item-specific, vendor-validated application protocols (e.g., WB, IHC, IF, FC) are provided for this small-molecule ligand.

General guidance for use as a research tool compound (literature-informed; adapt to your system):

• Stock solution: prepare 10–50 mM in dry DMSO. Aliquot under inert gas to minimize oxidation/moisture uptake and store at −20 °C.
• In vitro receptor assays: perform serial dilutions in assay buffer containing 0.1–1% DMSO (final). Include vehicle controls to correct for solvent effects. Equilibrate sufficiently based on expected receptor kinetics.
• Binding assays: verify nonspecific binding by including high-concentration known antagonist. Assess potential interference with detection (e.g., fluorescence quenching) due to aromatic chromophores.
• Cell-based assays: confirm absence of precipitation/micelles by visual inspection or nephelometry after dosing. Consider slightly acidic buffer to enhance solubility via protonation (if viable for the biology).
• Analytical use: for LC–MS calibration, prepare a multi-point curve (≥6 points) bracketing expected concentrations. Use an internal standard and evaluate carryover due to lipophilicity.

These are generic suggestions; develop and validate your own SOPs. For any detailed, item-specific protocol, refer to lab-validated methods and the CoA/SDS for handling constraints.

Biological Roles

General literature context (not item-specific; no clinical claims):

• Pharmacological class: ethanolamine-ether antihistamine. Compounds of this chemotype act as inverse agonists/antagonists at the histamine H1 receptor (H1R) in vitro, stabilizing the inactive receptor conformation and preventing histamine-mediated signaling.
• Polypharmacology: Like other lipophilic tertiary amines, related structures can exhibit ancillary interactions with muscarinic acetylcholine receptors and other CNS-relevant targets in binding assays, reflecting their cationic amphiphile character (literature observations). Such findings underscore the need for cross-target profiling when used as tool compounds.
• Ionization and membranes: The basic tertiary amine (protonated near physiological pH) leads to pH-partitioning behavior, lysosomal sequestration, and potential phospholipidosis signals in cell systems at higher exposures (class effect; literature). Careful dosing and control experiments are recommended.
• ADME-relevant traits (in vitro): Rapid on–off kinetics at H1R are typical within the ethanolamine class; high plasma protein binding and significant microsomal metabolism (O-dealkylation, N-dealkylation) are commonly reported for analogs (literature).
• Research uses:
  • Benchmark antagonist in receptor-binding competition assays and functional H1R readouts (e.g., calcium mobilization in engineered cell lines).
  • Reference standard in analytical panels screening first-generation antihistamines.

Notes and cautions:

• For research use only. Not for human or veterinary use.
• Always confirm the salt/counterion and exact concentration in biological media; adsorption to plastics and precipitation upon dilution can confound results.

Buffer Applications

This product is not a buffering reagent. It does not constitute a classical acid–base buffer system with a defined buffering range. Accordingly:

• Typical buffer preparation guidance (e.g., phosphate, HEPES, Tris) is not applicable.
• For assay work, prepare stock solutions in DMSO or ethanol and dilute into the desired biological buffer immediately before use. Mild acidification of the buffer (pH 5–6) may enhance solubility by protonating the tertiary amine (general literature guidance), provided this is compatible with the biological system.

For practical buffer selection, prioritize the requirements of the biological assay (ionic strength, pH stability, metal chelation) rather than properties of this ligand. Validate clarity and absence of precipitation after dosing into buffer.

Green Alternatives

As a small-molecule ligand/research standard, this product itself is not a consumable solvent or reagent typically replaced for greener process mass improvements. However, greener practice considerations apply to its handling and solution preparation:

• Preferred solvents for stock solutions:

  • Use ethanol or water (with mild acidification to solubilize the amine) where feasible, instead of high-toxicity dipolar aprotics (e.g., DMF, NMP). DMSO remains widely accepted for screening; manage volumes to keep final assay solvent ≤1–2% v/v.

• Waste minimization:

  • Prepare concentrated master stocks to reduce total solvent usage; aliquot to avoid repeated thawing and disposal of expired solutions.
  • Employ microscale assays and high-throughput formats to lower per-experiment consumption.

• Comparative considerations (general):

  • DMF vs. ethanol/DMSO: DMF offers strong solvation but higher toxicity and environmental burden; ethanol or DMSO are generally preferred in biological testing.
  • Chlorinated solvents: avoid for routine solution prep; reserve for necessary analytical extractions, substituting with ethyl acetate or isopropanol where compatible.

• Packaging/handling:

  • Use amber vials and inert headspace (as provided) to extend shelf life, reducing the need for repeated resynthesis and associated environmental impact.

Note: No claims are made regarding the inherent “greenness” of the active itself; guidance focuses on solvent choice and laboratory practices.

Pharmaceutical Uses

No formulation/excipient role or pharmacopeial grade is specified for this catalog item. This product is supplied strictly for research use only.

General literature context (not item-specific; no therapeutic claims):

• The phenyltoloxamine chemotype has historically appeared as an active pharmaceutical ingredient (API) in legacy products. In research and development settings, the compound may be used as a reference standard for analytical method development and as a comparator in preclinical formulation studies.

R&D formulation considerations (laboratory context only):

• Salt selection can markedly affect solubility and stability (e.g., hydrochloride, citrate; literature). The free base may require co-solvents or pH adjustment for aqueous dosing.
• Typical vehicles for preclinical studies (not recommendations for this specific product) include DMSO/PEG-400/saline mixtures or ethanol/solutol systems; compatibility must be established experimentally and institutional guidelines followed.

Regulatory status for this specific item: Not applicable; no pharmacopeial/compendial status or GMP qualification is claimed. Refer to the CoA for the research-grade specifications only.

Physical Properties

Item-specific numerical specifications (BP/MP/density/UV cutoff, etc.): Not specified for this item; refer to CoA/Spec Sheet.

General physical-chemical profile (literature/typical for tertiary-amine aryl ether bases; not item-specific):

• Appearance: commonly isolated as a free base (oily/low-melting solid) or as crystalline salts (e.g., HCl, citrate) with improved handling and aqueous solubility.
• Ionization: tertiary amine pKa (conjugate acid) for related ethanolamine ether antihistamines typically ~8.5–9.5 (literature). Protonation markedly increases water solubility.
• Solubility trends:
  • Free base: high solubility in organic solvents (DMSO, DMF, ethanol, chloroform, ethyl acetate); limited aqueous solubility at neutral/basic pH.
  • Acid salts: substantially more water-soluble, facilitating bioassays and analytical standards.
• Lipophilicity: aryl ether tertiary amines of this class exhibit moderate-to-high logP in the neutral form (literature), decreasing upon protonation.
• Volatility: low; non-volatile organic base.
• Hygroscopicity: tertiary amine salts may be mildly hygroscopic; free base less so. Store under inert atmosphere as directed.

Refractive index, boiling/melting points, density, and spectral cutoffs: Not specified for this item; refer to CoA/Spec Sheet.

Practical notes:

• Prepare concentrated stocks in dry DMSO or ethanol, then dilute into assay buffer immediately before use to limit precipitation.
• If handling as the free base, gentle warming (≤40 °C) may assist dissolution in organic media; avoid prolonged heating.

Quality and Grades

• Item-specific grade: Moligand™ (from Product Data).
  • Interpretation: Moligand™ is typically used to denote small-molecule ligands provided for research screening, target engagement studies, binding assays, and chemical biology. Such materials are intended for research use only and are not formulated for clinical or diagnostic applications.

What to expect from Moligand™-grade material (general guidance):

• Emphasis on identity and suitability as a ligand/biological probe standard, enabling preparation of stock solutions for in vitro experiments, binding assays, or analytical reference work.
• UV/background: While many ligand-grade materials are suitable for spectroscopic/LC-MS workflows, low-UV or LC/MS-grade specifications (e.g., UV cutoff, metal content) are NOT implied unless explicitly stated. For this item: Not specified for this item; refer to CoA/Spec Sheet.
• Residual solvent profile, water content, and impurity limits: Not specified for this item; refer to CoA/Spec Sheet.

Release documentation:

• For lot-specific purities, identity confirmation (e.g., HPLC, NMR, MS), and any stabilizers or counterions present, consult the CoA/Spec Sheet shipped with the product or available on request.

Use case alignment:

• Suitable for preparation of DMSO or ethanol stock solutions for biochemical assays, ligand screening, and as a reference compound in analytical method development.
• Not formulated as a chromatographic solvent or as a regulated pharmaceutical ingredient.

Reaction and Applications

This compound is primarily a bioactive small-molecule ligand and reference standard, not a general-purpose synthetic reagent. Accordingly, reaction chemistry is not its main use case. Relevant research applications include:

• Ligand/tool compound in receptor pharmacology (literature): leveraged as a representative ethanolamine-class H1 receptor antagonist for binding assays, off-target profiling, and structure–activity relationship (SAR) comparisons. No medical/clinical use is implied.
• Analytical reference: standard for method development or system suitability in LC–UV/LC–MS workflows evaluating antihistamine-class analytes. Validate extinction coefficients and response factors experimentally.
• Permeability/ADME model compound (in vitro): employed as a test article in membrane transport and microsomal stability assays to benchmark tertiary-amine aryl ethers (literature use cases). Ensure proper controls and solvent normalization.

If used in chemical transformations (less common):

• The tertiary amine can be quaternized to form ammonium salts; the ether is generally stable toward mild bases and nucleophiles; benzylic positions (if present) may undergo oxidative or electrophilic transformations under forcing conditions (literature, not recommended for routine synthesis with this expensive ligand-grade material).

Practical guidance:

• Maintain anhydrous conditions for long-term DMSO stocks; minimize freeze–thaw cycles.
• Conduct adsorption checks in plasticware; lipophilic amines can exhibit non-specific binding.
• Document exact salt form (if any) from the CoA for mass-balance calculations.

Reaction Conditions

This product is not typically employed as a reagent or substrate in named synthetic reactions; no item-specific reaction condition data are provided.

General laboratory handling for solution preparation (research assay context; not item-specific):

• Stock preparation: 10–50 mM in anhydrous DMSO (or ethanol) is common for lipophilic tertiary amines. Sonication or brief warming (≤40 °C) can aid dissolution. Record exact concentration by weight-in or quantitative NMR if needed.
• Working solutions: dilute stocks into assay buffer or culture media immediately before use, targeting final solvent ≤1–2% v/v. To mitigate precipitation, add stock slowly with mixing and consider slightly acidic buffers to maintain protonation of the amine (if assay-compatible).
• Filtration: 0.22 µm PVDF or PTFE filters can be used for sterilization/clarity.

If transformation studies are undertaken (literature-level expectations only):

• Quaternization: tertiary amine + MeI/EtI or benzyl halides in acetonitrile or acetone, RT–reflux, hours to overnight.
• Salt formation: dissolve base in minimal ethanol/EtOAc and gas with dry HCl, or titrate with standardized HCl in ether to precipitate the hydrochloride salt.

Note: No yields, kinetics, or optimal catalysts are provided for this item. Consult primary literature if performing chemical modifications.

Safety and Handling

Authoritative safety data (GHS classification, signal word, H/P statements, pictograms) for this catalog item: Not specified for this item; refer to the product SDS.

General laboratory precautions for tertiary amine aryl ether bases (literature; not item-specific):

• PPE: wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to avoid exposure to dust/vapors/aerosols.
• Avoid: inhalation, ingestion, and skin/eye contact. Wash thoroughly after handling. Prevent environmental release.
• Incompatibilities: strong oxidizers; strong acids/bases (may cause decomposition or exotherm). Amines can react with acylating agents and some halogenating agents.
• First aid (general guidance; defer to SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing; obtain medical advice.
  • Ingestion: rinse mouth; do not induce vomiting unless directed by medical personnel.
• Fire safety: treat as combustible organic. Use CO2, dry chemical, or foam. Thermal decomposition may generate irritating fumes (nitrogen oxides, CO/CO2).
• Spill response: absorb with inert material, collect for disposal in chemical waste. Decontaminate area with suitable solvent/detergent while observing compatibility.

Storage and shipping (item-specific from Product Data):

• Storage: Store at −20 °C, argon charged.
• Shipping: Shipped in ice chest with ice pads.

Always consult the SDS for definitive hazard, exposure limits, and emergency measures.

Solvent Selection

This product is a small-molecule tertiary amine ligand rather than a bulk solvent. Solvent selection guidance below focuses on preparing stock solutions and working dilutions for research assays.

• Primary stock solvents (general best practices):

  • DMSO (anhydrous): excellent solvating power for aryl ether tertiary amines; widely used for high-concentration stocks (10–100 mM). Filter-sterilizable; miscible with water for subsequent dilutions.
  • Ethanol or isopropanol: suitable for moderately concentrated stocks; consider compatibility with biological systems and final solvent percentages (<1–2% v/v in assays).
  • DMF: strong solvent but less favored in biological testing due to cytotoxicity; limit final assay concentrations.

• Aqueous media:

  • Free base: limited water solubility at neutral pH; solubility increases in mildly acidic buffers (pH 5–6) due to amine protonation (literature behavior for tertiary amines).
  • Salts (if applicable): enhanced aqueous solubility; verify counterion on CoA.

• Miscibility/polarity notes (general/literature):

  • Neutral, lipophilic base; exhibits good solubility in mid- to low-polarity organic solvents (EtOAc, CHCl3); practically insoluble in alkanes.

• Practical tips:

  • Prepare concentrated DMSO stocks and dilute into buffer immediately before use to minimize precipitation.
  • Pre-acidify aqueous diluents slightly (e.g., with HCl to pH ~5–6) to maintain the amine in protonated form and improve clarity, where compatible with the assay.
  • Filter 0.22 µm if needed; avoid adsorptive plastics for very lipophilic solutions (use glass or low-bind plastics).

Storage and Reconstitution

Item-specific storage and shipping (from Product Data):

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

General reconstitution and handling guidance (for small-molecule tertiary amine ligands; not item-specific):

• Upon receipt: Allow the sealed container to equilibrate to room temperature before opening to prevent condensation. Open under dry inert gas if possible, especially for hygroscopic salts or moisture-sensitive free bases.
• Stock solutions:
  • Prepare concentrated stocks in anhydrous DMSO (typ. 10–50 mM) or ethanol. Record exact mass, solvent, and final volume. Mix until fully dissolved; brief sonication can help.
  • If aqueous stocks are required, consider preparing a salt (if permitted) or dissolve in mildly acidic buffer to protonate the amine. Verify clarity and stability.
• Aliquoting: Dispense single-use aliquots in amber vials or low-bind tubes under inert atmosphere to minimize oxidation and adsorption. Avoid repeated freeze–thaw cycles.
• Stability considerations:
  • Protect from light and moisture. Maintain argon or nitrogen headspace after each use.
  • Monitor for discoloration or precipitation; discard if significant changes are observed or if outside CoA-defined retest date.
• Disposal: Collect unused solutions and rinsates as organic chemical waste per institutional and local regulations.

For any lot-specific stability data (e.g., retest period, impurity profile), consult the CoA/Spec Sheet.

Structure and Identity

Short description: Phenyltoloxamine is an ethanolamine ether tertiary amine belonging to the diphenyl/arylmethyl-ether antihistamine chemotype (structurally related to diphenhydramine), typically featuring a benzhydrylic ether core bearing one phenyl and one tolyl ring and a 2-(dimethylamino)ethyl side chain.

• Item-specific identifiers (from Product Data):

  • CAS: 92-12-6
  • CID: 7077
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Molecular identity (general literature description; not item-specific):

  • Functional groups: tertiary amine (dimethylamino), ether (aryloxymethyl-ether), benzhydrylic center bearing an aryl (phenyl) and an aryl-methyl (tolyl) substituent.
  • Ring systems: two aromatic rings (one phenyl, one methyl-substituted phenyl/tolyl).
  • Protonation state: typically a neutral, lipophilic tertiary amine base; readily forms salts with mineral acids (e.g., HCl, citrate) for improved aqueous solubility (literature).
  • 2D structure in words: an aryl–CH(Ar′)–O–CH2–CH2–N(CH3)2 scaffold, where Ar = phenyl and Ar′ = tolyl (methyl-substituted phenyl) in common representations (literature).

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

Notes:

• All structural specifics above (beyond CAS/CID) are provided as general literature context for the phenyltoloxamine chemotype and should not be interpreted as the certified identity fields for this specific lot. Consult the CoA for definitive identifiers.

Synthetic Utility

This compound is primarily intended as a bioactive ligand/reference standard, not as a synthetic intermediate. However, from a retrosynthetic and functional-group perspective (general literature context):

• Functional groups and reactivity:

  • Tertiary amine: amenable to quaternization (alkyl halides), protonation (salt formation), and oxidative N-dealkylation under metabolic or strong chemical conditions.
  • Aryl ether (benzhydrylic ether): typically robust to bases/nucleophiles; can undergo O-dealkylation under strong Lewis/Brønsted acids or oxidative conditions.
  • Benzylic center: in related benzhydrylic systems, electrophilic substitutions or oxidations at activated positions are documented but often lead to complex mixtures.

• Representative transformations (for analog synthesis; literature):

  • Ether formation via SN1/SN2 strategies from benzhydrol/arylmethyl halides with ethanolamine derivatives.
  • Reductive amination or alkylation routes to install the dimethylaminoethyl side chain.
  • Salt formation (HCl, citrate, fumarate) to modulate solid-state properties for purification.

• Utility in method development:

  • Serves as a probe to challenge analytical separations of basic, lipophilic aryl ethers (LC method scouting, buffer/ion-pair optimization).

Given the value of the material as a reference ligand, routine derivatization is generally discouraged unless your program specifically targets analog generation. For synthetic-grade material and building-block specifications, consult alternative catalog entries.

Target Specificity

Item-specific target data (antigen/epitope/clone/isotype/species) are not applicable; this is a small-molecule ligand, not an antibody or protein reagent.

For the phenyltoloxamine chemotype in literature (not item-specific):

• Primary pharmacological target: histamine H1 receptor (H1R), where ethanolamine-class antagonists act as inverse agonists/antagonists in binding/functional assays.
• Off-target considerations: potential ancillary binding at muscarinic receptors and other CNS GPCRs has been reported for related first-generation antihistamines; specificity should be empirically profiled for your system.

This catalog listing provides no certified target-binding data or potency values. For quantitative parameters (Ki, IC50), consult peer-reviewed literature and verify under your assay conditions.