This compound belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof.
External Descriptors
Not available
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
297.300 g/mol
XLogP3
2.000
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Exact Mass
297.136 Da
Monoisotopic Mass
297.136 Da
Topological Polar Surface Area
30.900 Ų
Heavy Atom Count
22
Formal Charge
0
Complexity
530.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
2
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
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Application Protocols
No assay protocols are validated or provided for this specific SKU. The following general, literature-based examples illustrate how small-molecule alkaloids like erythraline might be handled in common research workflows:
Stock preparation (analytical/bioassay):
Prepare a 10 mM stock in DMSO (or MeOH if compatible). Filter through a 0.22 μm PTFE filter. Store aliquots to minimize freeze–thaw.
For aqueous assays, dilute into buffer to ≤1% DMSO final. If turbidity forms, acidify slightly (e.g., 0.1% formic acid) or use the hydrochloride salt.
LC–MS quantitation (example):
Build a 6–8 point calibration curve (1–1000 ng/mL) in matrix-matched solvent with isotopically labeled or structural analog internal standard. Use RP-C18, water–acetonitrile + 0.1% formic acid. Monitor [M+H]+ in positive ESI.
Stability check:
Incubate at room temperature and 40 °C in intended solvent; sample at 0, 24, 72 h; analyze by LC–MS for degradation or epimerization.
These are general examples only and are not item-specific, validated procedures. Users should develop and validate protocols for their own systems.
Biological Roles
Literature context for Erythrina-type alkaloids (including erythraline):
Ecological/plant role: Erythrina spp. produce erythrinan alkaloids as specialized metabolites, often implicated in plant defense.
Molecular pharmacology (research context): Many Erythrina alkaloids act as modulators or antagonists at neuronal nicotinic acetylcholine receptors (nAChRs); some also influence GABAergic or other ligand-gated ion channels in in vitro systems. Potency and selectivity vary with substitution and stereochemistry.
Biophysical probes: Due to their rigid, stereochemically rich scaffolds, these alkaloids serve as conformational probes to interrogate receptor binding pockets and as benchmarks in docking/MD simulations.
Metabolism (general): Tertiary amines typically undergo phase I N-oxidation/dealkylation and phenolic O-dealkylation, followed by phase II conjugation (e.g., glucuronidation/sulfation) in mammalian systems; exact pathways are structure-dependent and must be determined experimentally for erythraline.
Important: The statements above summarize literature/general knowledge for the class and do not constitute medical or clinical claims. All work with erythraline should be conducted strictly for research purposes, adhering to institutional biosafety and ethical guidelines.
Buffer Applications
This product is a small-molecule alkaloid standard and is not typically used to prepare buffer systems. However, when formulating assay solutions:
Preparing aqueous assay media (general guidance):
Dissolve erythraline first in a miscible organic co-solvent (e.g., DMSO or MeOH), then dilute into a physiological buffer (e.g., PBS, HEPES, or acetate buffer), keeping final organic content typically ≤1–2% v/v to avoid precipitation or biological confounds.
For improved solubility, adjust the buffer to mildly acidic pH (≈5–6) or prepare an acid addition salt (e.g., HCl salt) before dilution.
Suggested buffer ranges for related tasks (literature):
Acetate buffer (pH 4–5.5): Enhances solubility of protonated amines.
HEPES (pH 7.2–7.6): Common for cell-free receptor assays; verify solubility as free base may precipitate near neutral pH.
These are general, literature-based practices for handling basic small molecules and are not item-specific specifications.
Green Alternatives
This SKU is a specialized natural product, not a process solvent or bulk reagent. “Green alternatives” therefore relate mainly to handling solvents and workflow choices rather than replacing the compound itself.
Greener solvent choices (literature/practice):
Prefer EtOAc, MeOH, EtOH, or 2-propanol over chlorinated solvents for routine dissolution/extraction when compatible with your assay.
For LC separations, water–acetonitrile systems generally have lower environmental impact than water–THF/CH2Cl2; consider buffered aqueous MeOH as another option.
Workup/design considerations:
Utilize acid–base partitioning to minimize solvent volumes and avoid silica when feasible (reduces waste from chromatography).
If preparative purification is required, reverse-phase flash/HPLC with aqueous-organic eluents often decreases halogenated solvent usage.
Trade-offs:
Some erythrinan alkaloids dissolve better in CH2Cl2/CHCl3; greener substitutes may require higher volumes or co-solvents, potentially impacting recovery.
DMSO is effective but persistent; plan for appropriate waste handling.
Summary table (general):
CH2Cl2/CHCl3 → Prefer EtOAc/MeOH when solubility allows.
Hexanes for normal-phase → Consider heptane or cyclopentyl methyl ether (CPME) where applicable.
THF → Consider 2-MeTHF for extractions if compatible with downstream analyses.
These recommendations are general and should be verified for your specific method/assay.
Pharmaceutical Uses
No excipient or pharmacopeial status is provided for this item. This product is supplied strictly for research use only and is not intended for human or veterinary use.
Literature/contextual information for formulation research with alkaloids:
Salt selection studies: Formation of hydrochloride, sulfate, or mesylate salts can modulate solubility, stability, and crystallinity for pre-formulation research.
Preclinical enabling research: Small-molecule alkaloids are often prepared as DMSO concentrates for in vitro assays; for in vivo exploratory work in animals (outside the scope of this catalog), vehicles may include aqueous buffers with cosolvents/surfactants (e.g., PEG400, Tween 80). Any such use must follow institutional approvals and is outside Aladdin Scientific’s intended use.
Stability screening: Conduct forced degradation (acid/base/oxidative/thermal/photo) and establish LC–MS stability-indicating methods to support storage and handling.
No medical or clinical claims are made. For any regulatory or GMP-related work, obtain appropriate grade/material and documentation from qualified suppliers.
Physical Properties
Item-specific specifications:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Melting point / Boiling point / Density / Refractive index / UV cutoff / Water content / Residual solvents: Not specified for this item; refer to CoA/Spec Sheet.
Handling-relevant characteristics (literature, for erythrinan alkaloids in general):
Physical state: Typically isolated as crystalline or amorphous solids.
Solubility: Free-base forms are commonly soluble in moderately polar organic solvents (e.g., CH2Cl2, EtOAc, MeOH, EtOH, acetonitrile) and sparingly soluble in water; solubility in water improves upon conversion to an acid addition salt (e.g., HCl, sulfate).
pKa (tertiary amine): Tertiary aliphatic amines often exhibit conjugate acid pKa in the ~8–10 range (literature, class-level guidance).
Partitioning: Free bases are typically lipophilic; salts are more hydrophilic (literature).
Spectroscopy: Exhibits characteristic aromatic signals in 1H/13C NMR; CD/optical rotation can be used to confirm stereochemistry (literature).
Note: For any certificate-bound values (mp, purity, exact solubility), please consult the item’s CoA/Spec Sheet. All non-specified values above are provided as general literature guidance for the erythrinan class rather than specifications for this SKU.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret common grades (general guidance):
Research grade / Reference standard: Suitable for discovery research, phytochemical profiling, SAR, and method development. Typically accompanied by identity confirmation (e.g., NMR, MS, HPLC/UPLC purity) on the CoA.
Analytical standard grade: Where offered, emphasizes traceable purity and identity with validated methods; supports quantitative analysis (e.g., calibration curves in LC–MS/UV).
Identity & purity confirmation recommendations (best practice for alkaloids):
Orthogonal ID tests: 1H/13C NMR, HRMS/ESI-MS, and, if chiral, optical rotation or chiral HPLC.
Purity assessment: HPLC/UPLC-UV (multiple wavelengths) and, where appropriate, ELSD/MS detection to capture non-UV impurities. Water/solvent content by Karl Fischer/GC if relevant to your application.
Stabilizers/Additives:
No stabilizer is specified for this item; refer to CoA/Spec Sheet. If offered as a salt or with an additive, review the CoA for counterion identity and assay basis (free base vs. salt).
Documentation:
Request the CoA matching your lot for exact purity, assay basis, residual solvents, and test methods. For traceability, retain LC/NMR spectra in your project file.
Reaction and Applications
Erythraline is primarily leveraged as a reference natural product for analytical, phytochemical, and chemical biology studies. It is not a commodity reagent; however, it can be used in the following research contexts (literature/general):
Analytical standard: Method development/validation for plant alkaloid profiling (LC–UV, LC–MS), retention-time indexing, and quantitative calibration.
SAR/target engagement: Reference ligand in receptor-binding or functional assays relevant to neuronal nicotinic acetylcholine receptors (nAChRs), a class where Erythrina alkaloids are frequently studied.
Derivatization studies: Functionalization at phenolic/methoxy positions (O-demethylation, O-acylation) and transformations at the tertiary amine (quaternization, N-oxide formation) to probe structure–activity relationships.
Stereochemical studies: Chiroptical and chiral-separation benchmarks for tetracyclic alkaloids.
Practical notes (literature):
Maintain anhydrous conditions for reactions sensitive to amines; tertiary amines can coordinate to Lewis acids and affect reaction rates/selectivities.
For salt–base interconversions, use dry HCl/MeOH to form the hydrochloride, or a mild base (NaHCO3) to free-base aqueous salt solutions; confirm form by NMR/HRMS.
During oxidative derivatization, control stoichiometry and monitor closely (e.g., DDQ or IBX for benzylic/phenolic oxidations), as over-oxidation can degrade the nitrogenous core.
Note: No manufacturer application specifics were provided beyond research use; all uses above are literature-based and for research only.
Reaction Conditions
General conditions relevant to derivatization or handling of erythrinan alkaloids (literature guidance; not item-specific specifications):
Salt formation (to enhance solubility/stability):
Dissolve free base in dry MeOH or iPrOH; bubble dry HCl gas or add 1–2 equiv acetyl chloride in MeOH at 0–25 °C; isolate the hydrochloride by concentration and precipitation with MTBE/Et2O.
O-demethylation (if aryl OMe present):
BBr3 (1–3 equiv) in CH2Cl2 at −78 to 0 °C, then quench with MeOH; monitor by TLC/LC–MS to avoid over-demethylation.
N-oxidation:
mCPBA (1.1–1.5 equiv) in CH2Cl2 at 0–25 °C affords the N-oxide; may be leveraged for Polonovski-type rearrangements.
Hydrogenation:
Pd/C (5–10%) under 1–3 atm H2 in EtOH/EtOAc at 25–50 °C for selective reduction of aryl–alkene or benzylic positions (substrate-dependent).
Analytical LC method (starting point):
RP-C18, 5 μm, 4.6×150 mm; mobile phase A: water + 0.1% formic acid; B: acetonitrile; gradient 10→70% B over 15 min; detection 210–280 nm; adjust as needed.
These conditions are representative examples from the broader erythrinan literature and should be optimized for your specific goals and substitution pattern.
Safety and Handling
GHS/Hazard 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: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General laboratory safety (applicable to bioactive alkaloids; literature/practice):
Handle in a chemical fume hood; avoid inhalation, ingestion, and skin contact. Many plant alkaloids are pharmacologically active at low doses.
Wear appropriate PPE: lab coat, safety glasses, and nitrile gloves. Change gloves frequently when working with powders.
Prevent dust formation; use antistatic measures and weighing boats with covers.
Incompatibilities: Strong oxidizers may degrade tertiary amines; strong bases/acids can induce salt/base conversions. Avoid prolonged exposure to light and moisture to minimize degradation.
First-aid overview (defer to SDS for authoritative instructions):
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing. Seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Spill/Disposal:
Avoid creating dust. Collect with damp disposable towels or HEPA-filtered vacuum. Dispose of according to institutional and local regulations for organic laboratory chemicals.
Always consult the product-specific SDS for definitive safety and regulatory guidance.
Solvent Selection
This product is a small-molecule alkaloid standard, not a bulk process solvent; solvent selection here refers to dissolving, handling, and analytical method development.
General solubility behavior (literature, erythrinan alkaloids):
Free base: Good solubility in MeOH, EtOH, acetonitrile, chloroform, and dichloromethane; limited solubility in water. Often soluble in DMSO for bioassays.
Acid salts (e.g., HCl salt): Enhanced aqueous solubility and stability in mildly acidic media (pH ~3–6).
Selection tips by application:
Analytical (HPLC/UPLC): Start with acetonitrile–water or methanol–water gradients containing 0.05–0.1% formic acid (or ammonium formate/acetate) to improve peak shape and ionization for LC–MS.
Preparative handling/stock solutions: DMSO or MeOH at 1–10 mg/mL, filter through 0.22 μm PTFE or PVDF. For aqueous dosing, dilute an aliquot of the organic stock into buffered media; add a small amount of acid if precipitation occurs.
Extraction/partitioning: Alkaloids partition to organic layers as free bases; protonation with dilute acid transfers them to the aqueous phase (classic acid–base workup).
Quick comparison (literature):
DMSO: Maximal solvency; ideal for small aliquots in screening; high boiling, hygroscopic.
MeOH/EtOH: Good solvency; volatile; compatible with most analytical workflows.
Acetonitrile: LC-friendly; lower viscosity; excellent for reverse-phase separations.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General best practices (literature/practice for alkaloids):
Store tightly capped in a desiccated environment, protected from light. If long-term storage is planned, consider refrigeration (2–8 °C) as a precaution unless the CoA/SDS advises otherwise.
Avoid repeated opening in humid environments; allow vial to equilibrate to room temperature before opening to reduce condensation.
Reconstitution guidance (general):
For analytical or screening use, prepare stocks at 1–10 mg/mL in DMSO or MeOH. If aqueous solution is required, dilute the organic stock into buffer; slight acidification (e.g., 0.05–0.1% formic or HCl) can help maintain solubility of the protonated form.
Filter solutions through a 0.22 μm PTFE/PVDF filter prior to sensitive assays.
Prepare single-use aliquots and minimize freeze–thaw cycles; for DMSO solutions, store at −20 °C to limit degradation and water uptake.
Always defer to the lot-specific CoA and SDS for authoritative storage and handling instructions for this SKU.
Structure and Identity
Brief overview: Erythraline is a naturally occurring Erythrina-type alkaloid. This product is offered as a research-grade small molecule standard.
Item-specific identifiers (from Product Data):
Product Name: Erythraline
CAS: 466-77-3
PubChem CID: 5317205
InChIKey: 351092 (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.
Structural class (literature):
Alkaloid family: Erythrinan alkaloids from Erythrina spp.
Core framework: Tetracyclic erythrinan skeleton featuring a bridged, partially saturated nitrogen-containing ring system fused to an aromatic ring.
Functional groups (typical for erythrinan alkaloids; literature): Tertiary amine, phenolic and/or methoxy substituents; some congeners bear a methylenedioxy substituent on the aromatic ring.
Stereochemistry: Multiple stereocenters embedded in the bicyclic/bridged portion of the core; naturally occurring isomers are typically well-defined stereochemically.
2D structure description (literature, generic for the class):
A fused aryl ring connected to a polycyclic saturated framework containing the ring nitrogen; oxygenated substituents (e.g., OMe/OH/O-CH2-O) often decorate the aryl ring; the tertiary amine is embedded within the bicyclic bridge.
Synthetic Utility
Although erythraline is typically a target molecule rather than a building block, it provides a valuable platform for synthetic and semi-synthetic investigations (literature):
Functional handles:
Tertiary amine: amenable to quaternization, N-oxide formation, reductive functionalization, or conversion to ammonium salts for SAR or crystallography.
Benzylic positions adjacent to the aromatic ring can be oxidized (DDQ/IBX) or reduced (hydrogenation) to tune electronics and conformation.
Chiral/scaffold studies: The rigid erythrinan core enables exploration of conformationally restricted ligands; late-stage diversification can map receptor pharmacophores.
Analytical utility: Serves as a reference for validating total synthesis routes of erythrinan frameworks; comparison of NMR, HRMS, and optical rotation ensures correct scaffold/stereochemistry.
Retrosynthetic relevance: Provides insights into strategies such as intramolecular Michael additions, radical cyclizations, or biomimetic rearrangements that forge the tetracyclic core (documented across the erythrinan family).
Note: Specific reactivity depends on erythraline’s exact substitution pattern; verify transformations on small scale and confirm structure after each step.
Target Specificity
No antibody/protein targeting or clone/isotype information applies to this small-molecule product.
Literature context: Erythrina alkaloids (the class to which erythraline belongs) have been investigated as ligands for neuronal nicotinic acetylcholine receptors (nAChRs) in research settings. Any binding selectivity or subtype preference must be determined experimentally for the exact compound and assay conditions and is not specified for this item.
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