Fendiline - Moligand™,≥98% , CAS No.13042-18-7

CAS: 13042-18-7 Cat. No.: F1074097 Fórmula: C₂₃H₂₅N Peso molecular: 315.45 Número EC: EINECS235-915-6

GRADE & PURITY Moligand™, ≥98%

Synonyms

3,3-Di(Phenyl)Propyl-(1-Phenylethyl)Amine | Divk1c_000604 | Ninds_000604

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Sinónimos

3,3-Di(Phenyl)Propyl-(1-Phenylethyl)Amine | Divk1c_000604 | Ninds_000604

Especificaciones y pureza

Moligand™,≥98%

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Tipo de acción

AGONIST

Pureza

≥98%

Nombres e identificadores

Sonrisas canónicas

CC(C1=CC=CC=C1)NCCC(C2=CC=CC=C2)C3=CC=CC=C3

IUPAC Name

3,3-diphenyl-N-(1-phenylethyl)propan-1-amine

InChIKey

NMKSAYKQLCHXDK-UHFFFAOYSA-N

INCHI

1S/C23H25N/c1-19(20-11-5-2-6-12-20)24-18-17-23(21-13-7-3-8-14-21)22-15-9-4-10-16-22/h2-16,19,23-24H,17-18H2,1H3

CAS alternativo

13636-18-5

Peso molecular

315.45

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Benzene and substituted derivatives
• Subclass: Diphenylmethanes
• Intermediate Tree Nodes: Not available
• Direct Parent: Diphenylmethanes
• Alternative Parents: Aralkylamines Dialkylamines Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Diphenylmethane - Aralkylamine - Secondary amine - Secondary aliphatic amine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Amine - Aromatic homomonocyclic compound
• Descripción: 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

Propiedades químicas y físicas

• Peso molecular: 315.500 g/mol
• XLogP3: 5.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 315.199 Da
• Monoisotopic Mass: 315.199 Da
• Topological Polar Surface Area: 12.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 303.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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

• Item-specific, tested application protocols: Not specified for this item; refer to CoA/Spec Sheet.
• General protocol examples (literature/practice guidance):
  1. Preparation of DMSO stock for cell assays
     • Warm compound and DMSO to room temperature. Weigh required amount quickly to minimize moisture exposure.
     • Dissolve to 10–50 mM. Vortex and sonicate briefly if needed. Aliquot into amber vials/tubes. Store at -20°C.
  2. Acute Ca2+ influx assay (fluorescent dye readout)
     • Load adherent cells with Fluo-4 AM per manufacturer’s instructions. Wash and equilibrate in HEPES-buffered saline (HBSS, 1–2 mM CaCl2).
     • Add compound from DMSO stock to desired final concentration (keep DMSO ≤0.1–0.2%).
     • Stimulate cells (e.g., depolarization with high K+ or agonist) and record fluorescence kinetics. Include vehicle and positive-control channel modulators as references.
  3. Concentration–response curve
     • Prepare 10-point half-log serial dilutions in assay buffer with constant DMSO.
     • Measure response, fit to a four-parameter logistic model, report apparent potency with confidence intervals.
• Notes: Validate compound stability under assay conditions and verify that any salt/vehicle used does not confound readouts.

Biological Roles

• Research role (literature/general):
  • Widely used as a small-molecule modulator in studies of calcium influx via voltage-gated calcium channels and the downstream effects on excitability, secretion, and signal transduction. Serves as a reference ligand to probe Ca2+-dependent pathways in cellular models.
  • As a lipophilic tertiary amine, it partitions into membranes and can influence ion channel gating and cellular calcium homeostasis, enabling dissection of calcium-linked transcription and metabolic responses (literature/general).
• Experimental considerations:
  • Off-target interactions are possible with other membrane proteins and ion transport processes; include orthogonal readouts (e.g., electrophysiology and Ca2+ imaging) to confirm mechanism.
  • Potency and selectivity can depend on membrane potential, subunit composition, and expression system. Titrate dose carefully and report free (unbound) concentration when feasible, as serum proteins can bind hydrophobic ligands.
  • Salt forms (if used) increase aqueous solubility and may alter apparent potency; specify the exact form and counterion in reports.
• Item-specific biological testing/targets: Not specified for this item; refer to CoA/Spec Sheet. All uses are for research only; not for human or veterinary use.

Buffer Applications

• This product is a hydrophobic small-molecule ligand and is not a buffering agent. It does not define or maintain pH like classical buffers (e.g., HEPES, Tris, phosphate).
• Practical note: When used in aqueous assays, prepare in DMSO or ethanol and dilute into the desired buffer (e.g., HEPES- or phosphate-buffered saline) keeping final organic solvent ≤0.1–0.5% v/v as assay permits. Mild acidification (compatible with biology) can improve solubilization via amine protonation.
• Item-specific buffer compatibility: Not specified for this item; refer to CoA/Spec Sheet.

Green Alternatives

• Context: This product is a small-molecule research ligand rather than a process solvent or bulk reagent. “Green alternatives” are primarily relevant to the choice of solvents, formulation vehicles, and waste minimization in its use.
• Solvent and formulation choices (general):
  • Prefer water-based assay media with minimal DMSO (≤0.1–0.5% v/v) when compatible with solubility and biology.
  • Consider ethanol (EtOH) or PEG-400/water cosolvent systems where assay-compatible and less problematic for waste segregation.
  • Avoid chlorinated solvents (e.g., CH2Cl2, CHCl3) unless necessary for analytics; use ethyl acetate or 2-MeTHF for extractions where possible.
• Small comparison (general guidance):
  • DMSO vs 2-pyrrolidone: DMSO is broadly compatible but penetrative; 2-pyrrolidone and NMP can improve solubility but have higher EHS concerns—use sparingly and with controls.
  • CH2Cl2 vs EtOAc: EtOAc offers lower toxicity and better environmental profile for workups, though solubility for very lipophilic amines may be lower.
• Operational green tips:
  • Prepare concentrated stock solutions to minimize solvent volume; aliquot to reduce waste from repeated thawing.
  • Use microscale assays and high-density plates to reduce material and solvent use.
• Item-specific environmental attributes: Not specified for this item; refer to SDS/CoA.

Pharmaceutical Uses

• Catalog intent: For research use only. Not for human or veterinary use.
• Formulation/excipient role: This compound is a small-molecule research ligand and is not used as a pharmaceutical excipient.
• Manufacturing/analysis context (general): In preclinical research, it may be formulated in DMSO, ethanol, or PEG-containing vehicles for in vitro studies; for any in vivo laboratory studies, follow institutional regulations and formulate to minimize vehicle-related confounders. No pharmacopeial monograph information is provided for this catalog item.
• Item-specific regulatory status and compendial references: Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

• Item-specific values: Not specified for this item; refer to CoA/Spec Sheet.
• Typical physicochemical characteristics for this compound class (literature/general guidance):
  • State: hydrophobic, oily or low-melting solid tertiary amine; free bases of this class are often oils at ambient temperature.
  • Solubility profile: generally sparingly soluble in water as free base; readily soluble in organic solvents such as DMSO, DMF, dichloromethane, chloroform, and ethanol (literature). Formation of salts (e.g., hydrochloride) increases aqueous solubility (literature).
  • Ionization: tertiary amine typically protonates with pKa of conjugate acid in the high-single-digit range (approx. 8–10; literature range for dialkylaryl tertiary amines). The free base will be more soluble at low pH due to protonation.
  • Lipophilicity: high logP is typical for diphenylalkylamines (literature), consistent with membrane permeability and nonpolar partitioning.
  • Refractive index, density, melting/boiling points, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet. Notes: All non-item-specific values above are generalized from literature on diphenylalkylamine tertiary amines and provided for method-development context only. Verify exact values on the CoA/SDS for this specific catalog item.

Quality and Grades

• Item-specific grade: Moligand™ (as stated in Product Data).
• What Moligand™ implies (general explanation):
  • Moligand™ indicates suitability for use as a small-molecule ligand in discovery workflows (e.g., target screening, biochemical/biophysical assays, cell-based perturbation studies). Emphasis is typically on identity, integrity, and practicality for screening rather than chromatographic solvent specifications.
  • Such materials are commonly qualified by NMR and/or LC–MS for identity and purity appropriate to research screening; however, exact tests, purity percentage, and impurity limits are Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers, residual solvents, and trace metals:
  • Not specified for this item; refer to CoA/Spec Sheet. If low UV background or metal content is critical (e.g., biophysical binding assays, metalloprotein studies), request the latest CoA.
• Fit-for-purpose guidance:
  • For biochemical screening, prepare fresh DMSO stocks and minimize freeze–thaw to maintain integrity.
  • For analytical method development (HPLC/LC–MS), verify UV/ESI behavior and any stabilizers on the CoA prior to quantitative assays.

Reaction and Applications

• This catalog item is positioned as a Moligand™ small-molecule ligand intended for research screening and chemical biology. Typical research uses (literature/general) include:
  • As a probe for voltage-gated calcium channel function and calcium-dependent signaling cascades. Used in mechanistic studies to perturb Ca2+ influx and analyze downstream phosphorylation and transcriptional responses in cells.
  • Tool compound for membrane biophysics and cation homeostasis studies; hydrophobic tertiary amines can partition into membranes and modulate ion channel behavior (literature/general).
• Assay development tips (general):
  • Prepare concentrated DMSO stocks (e.g., 10–50 mM), filter-sterilize when needed, and aliquot to minimize freeze–thaw. Validate assay tolerance to DMSO.
  • For Ca2+ imaging (e.g., Fluo-4/Fura-2), pre-equilibrate cells and add compound under controlled buffering; include vehicle controls and, where appropriate, positive control blockers for benchmarking.
  • Perform concentration–response experiments spanning at least 8–10 half-log units to define potency and assess off-target effects; include washout tests to evaluate reversibility.
• Synthetic/reagent applications:
  • As a finished, tertiary-amine small molecule, it is not commonly used as a synthetic reagent. Basicity enables salt formation, ion-pair extraction, or quaternization in methodological studies, but this is not its primary use-case.
• Item-specific application testing: Not specified for this item; refer to CoA/Spec Sheet and the Manufacturer Applications note for your lot (if available).

Reaction Conditions

• Not primarily applicable: This is a small-molecule ligand used as a probe in assays rather than as a reagent in synthetic transformations.
• Assay-oriented conditions (general/literature guidance):
  • Stock preparation: dissolve in anhydrous DMSO at 10–50 mM; vortex and, if necessary, sonicate gently. Filter (0.22 μm PTFE) for sterile applications.
  • Working concentration ranges: cell-based assays often explore 0.03–30 μM; biochemical binding assays may require broader ranges depending on target expression and binding affinity. Optimize per system and include vehicle controls.
  • Incubation: preincubate 10–30 minutes for acute effects on ion channels; longer exposures may be used for gene-expression endpoints—validate stability and avoid light/heat.
  • Media: use serum-free or low-serum conditions when assessing direct target engagement to reduce nonspecific binding of hydrophobic ligands.
• Item-specific tested conditions or yields: Not specified for this item; refer to CoA/Spec Sheet.

Safety and Handling

• GHS information (item-specific):
  • Signal Word: Not specified for this item; refer to SDS.
  • Hazard Statements: Not specified for this item; refer to SDS.
  • GHS Classification/Pictograms: Not specified for this item; refer to SDS.
• General laboratory safety guidance (literature/general):
  • Handle in a fume hood and avoid inhalation, ingestion, and skin/eye contact. Tertiary amines can be skin/eye irritants and may have strong odors.
  • Personal protective equipment: lab coat, gloves (nitrile), and safety goggles. Change gloves regularly when working with concentrated DMSO or other penetrating solvents.
  • Incompatibilities: strong oxidizers and strong acids/bases may cause decomposition or salt formation; avoid reactive acylating/alkylating agents unless intended.
  • First aid (overview; defer to SDS): rinse eyes/skin with water for at least 15 minutes upon contact; remove contaminated clothing; seek medical attention if symptoms persist. If inhaled, move to fresh air; if swallowed, rinse mouth—do not induce vomiting unless directed by medical personnel.
  • Waste: collect organic solutions for disposal as hazardous organic waste in accordance with institutional and local regulations.
• Storage from Product Data: Store at -20°C. Shipments are cold-packed (ice chest + ice pads). Protect from moisture; keep container tightly closed. Always consult the product-specific SDS for authoritative guidance.

Solvent Selection

• Practical solvent choices (general/literature for this compound class):
  • Stock solutions: DMSO is the primary choice due to high solvating power for lipophilic tertiary amines and assay compatibility. Ethanol or methanol can also be used for certain biological assays; DMF is an alternative for chemical workflows.
  • Working solutions: dilute DMSO stocks into aqueous buffers with surfactants (e.g., 0.01–0.1% Tween-20) or with co-solvents (≤0.1–0.5% DMSO v/v in final assay) to mitigate precipitation in physiological media. Adjust pH below the amine pKa (acidify mildly) to improve aqueous solubility via protonation when compatible with the assay.
• Polarity/miscibility (general):
  • As a hydrophobic tertiary amine, the free base is poorly miscible in water and readily soluble in mid- to low-polarity organics (DMSO, DMF, dichloromethane, chloroform, ethyl acetate, alcohols; literature).
• When to choose alternatives:
  • If water solubility is essential, consider preparing an acid addition salt (e.g., HCl, citrate) or using cyclodextrin inclusion, micelles, or lipid carriers in biological assays.
  • For air- and moisture-sensitive chemistries, use anhydrous solvents and inert atmosphere to prevent amine protonation or oxidation side processes.
• Item-specific solubility/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Storage and Reconstitution

• Item-specific storage from Product Data:
  • Store at -20°C. Shipped in ice chest with ice pads.
• General handling recommendations:
  • Keep tightly capped under dry, inert atmosphere if possible. Allow vials to equilibrate to room temperature before opening to minimize moisture condensation.
  • Protect from light and repeated freeze–thaw; aliquot upon first receipt.
• Reconstitution guidance (general):
  • For biochemical/cellular assays, prepare concentrated stocks in anhydrous DMSO (e.g., 10–50 mM). If higher aqueous solubility is needed, prepare a suitable acid addition salt immediately prior to use or dilute into buffered media with gentle acidification when compatible with the system.
  • Filter sterilize (0.22 μm PTFE) for cell-based work if necessary.
• Stability/shelf life:
  • Item-specific shelf life and stability data are Not specified for this item; refer to CoA/Spec Sheet and SDS. If prolonged storage is required, maintain at -20°C or below and avoid prolonged exposure to ambient humidity and temperature.
• Research Use Only: As indicated by the supplier; not for human or veterinary use.

Structure and Identity

• Item-specific identifiers from Product Data:
  • CAS: 13042-18-7
  • CID: 3336
  • InChIKey: 242317 (as supplied in Product Data)
  • 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.
• Nomenclature and scaffold notes (general/literature):
  • Fendiline is commonly classified among diphenylalkylamine-type small molecules and contains a tertiary amine center (literature). Such structures are typically highly lipophilic and feature two aromatic rings connected through an aliphatic chain to a dialkylamino group.
  • Functional groups (general class): tertiary amine; aromatic (phenyl) rings; benzylic/aliphatic C–C framework.
• 2D structural description (general, based on literature class):
  • A central aliphatic carbon chain bearing a tertiary dimethylamino substituent is flanked by two phenyl rings on a neighboring carbon (diphenyl-substituted propyl-type motif). No stereocenters are expected for the canonical free base within this scaffold class (literature).

Synthetic Utility

• Role in synthesis: This product is supplied as a finished small-molecule ligand and is not typically used as a synthetic building block.
• Chemical features (general):
  • Tertiary amine can undergo salt formation (e.g., HCl, mesylate, citrate) for isolation or solubility modulation.
  • Quaternization (alkyl halides, MeI) affords quaternary ammonium salts—useful for generating permanently charged analogs in SAR studies.
  • N-oxide formation (mCPBA) and subsequent rearrangements can be explored for mechanistic or metabolite-mimic studies.
  • Aromatic rings enable late-stage electrophilic substitutions or cross-coupling on suitably functionalized analogs, but the parent compound typically lacks handles for direct coupling without prior derivatization (literature/general).
• Retrosynthetic value: Limited, unless used as a scaffold reference for analog design in medicinal chemistry. For library work, analog generation focuses on adjusting amine substituents, ring electronics, and linker length to tune potency and physicochemical properties.

Target Specificity

• Item-specific, validated target(s), Kd/IC50, selectivity panels, and species reactivity: Not specified for this item; refer to CoA/Spec Sheet.
• General/literature context:
  • Frequently used as a research tool to modulate voltage-gated calcium channels in cellular systems. Reported functional effects can vary with channel subtype composition and membrane potential (literature). Off-target interactions are possible; confirm mechanism with orthogonal assays.
• Recommendation: For target deconvolution, complement pharmacology with genetic knockdown/knockout controls, chemical orthologs, and, where possible, biophysical binding assays.