Geissoschizoline , CAS No.18397-07-4

CAS: 18397-07-4 Cat. No.: G1445768 Formula: C₁₉H₂₆N₂O Peso molecolare: 298.42

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

Geissoschizoline ((+)-Geissoschizoline) is a potent inhibitor of human AChE/BChE , with IC 50 s of 20.40 µM and 10.21 µM, respectively. Geissoschizoline emerges as a possible multi-target prototype that can be very useful in studies of preventing neurodegeneration and restoring neurotransmission. Geissoschizoline aiso is a potent anti-inflammatory agent.

Specifiche

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

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

Tipo di azione

INHIBITOR

Nomi e identificatori

Peso molecolare

298.42

Application Protocols

No item-specific tested application protocols are provided in the Product Data.

General usage guidance for small-molecule standards (not item-specific):

• Stock preparation:
  • Prepare a concentrated stock in DMSO, methanol, or acetonitrile (typical 5–50 mg/mL). If aqueous delivery is required, consider forming a dilute acid salt and filter-sterilize (0.2 µm) if sterility is necessary for the application.
• Analytical method development:
  • Start with RP-LC: Water/MeCN (or MeOH) gradient with 0.05–0.1% formic acid; monitor at 220–290 nm and by ESI-MS.
• Solid-phase extraction (SPE):
  • Cation-exchange or reversed-phase cartridges can be used for sample cleanup; condition with MeOH and equilibrate with aqueous acid.
• Stability checks:
  • Perform short-term stress tests (light, air, mild acid/base) to establish handling windows; use amber vials and minimize freeze–thaw cycles.

These are general recommendations; optimize for your specific matrix and detection method.

Biological Roles

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

• Biosynthetic origin:
  • Geissoschizoline belongs to the monoterpenoid indole alkaloids, typically biosynthesized in plants via condensation of tryptamine (from the shikimate/tryptophan pathway) with secologanin (from the iridoid/terpenoid pathway) to form strictosidine, followed by enzyme-catalyzed rearrangements leading to aspidospermane-like frameworks.
• Ecological function:
  • Indole alkaloids often serve as plant defense metabolites against herbivores and pathogens, with roles in deterrence and allelopathy proposed in the literature.
• Chemical biology utility:
  • Due to the indole chromophore and basic nitrogen, these alkaloids can be tracked by LC–MS and fluorescence/UV detection, facilitating metabolomics and biotransformation studies.
• Metabolic transformations (general):
  • Oxidative metabolism at the indole ring and N-dealkylation/oxidation at the tertiary amine are common in biotic/abiotic contexts.
• Protein binding/partitioning:
  • Protonatable nitrogen and aromatic system suggest pH-dependent membrane partitioning and possible noncovalent interactions (π–π, cation–π) in biochemical systems; specific targets for geissoschizoline are not established here.

Note: These are general roles for the class; detailed biological properties and specific interactions for Geissoschizoline should be sourced from primary literature or the product’s CoA if provided.

Buffer Applications

This product is a small-molecule indole alkaloid and is not a conventional buffering agent. It does not form a defined buffer system in water under typical laboratory conditions.

Practical notes (general):

• For analytical work (HPLC/LC–MS), mildly acidic aqueous mobile phases (e.g., 0.05–0.1% formic acid) often improve peak shape of basic analytes.
• To prepare aqueous stocks, convert to a salt form (e.g., dilute HCl or TFA) to enhance solubility, then dilute into the desired assay buffer. Confirm compatibility of the counterion with your assay.

If a true buffer is required, use established systems (phosphate, acetate, formate, HEPES, MOPS) in their appropriate pH ranges and keep the alkaloid as an analyte, not as a buffering species.

Green Alternatives

Context: As a target small molecule, Geissoschizoline itself is not replaceable; however, greener choices can be made for its handling, purification, and analysis.

Greener solvent considerations (general guidance):

• Replace chlorinated solvents:
  • Prefer ethyl acetate or 2-MeTHF over chloroform/DCM for extractions and chromatography when separation allows.
• Use bio-based/safer solvents:
  • Ethyl acetate, isopropanol, methanol (biobased grades available), water mixtures for RP chromatography.
• Minimize TFA use:
  • Use formic or acetic acid as volatile modifiers where peak shape and ionization remain acceptable.
• Concentration and work-up:
  • Employ lower-energy solvent removal (rotary evaporation under reduced pressure) and solvent recycling where possible.

Illustrative comparison (general, not item-specific):

• DCM vs 2-MeTHF:
  • DCM: excellent eluent strength, but high environmental/health concerns.
  • 2-MeTHF: renewable origin, wider liquid range, water-immiscible; may require method re-optimization.
• CHCl3 vs EtOAc:
  • CHCl3: strong solvency but toxic; EtOAc: safer, biodegradable, often adequate for normal-phase separations.

Operational best practices:

• Scale-down extractions and use SPE to reduce solvent volumes.
• Favor RP-HPLC with water/MeCN or water/MeOH gradients and aqueous buffers at low percentages.
• Implement closed-transfer and solvent recovery systems in routine prep.

Pharmaceutical Uses

No excipient or pharmacopeial status is provided in the Product Data for Geissoschizoline. This listing is for research use only.

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

• Natural product standards: Indole alkaloids are frequently employed as analytical reference materials during natural product isolation, dereplication, and quality control of botanical preparations.
• Formulation experiments: When used in preclinical research, small-molecule alkaloids may be formulated as salts to improve solubility for in vitro assays. Common vehicles include aqueous acids (e.g., dilute HCl), aqueous ethanol, or DMSO stock solutions diluted into buffer.
• Regulatory note: Use in drug products would require comprehensive CMC, toxicology, and regulatory filings; none are implied here.

Recommendation: Treat Geissoschizoline strictly as a research chemical. For any formulation feasibility studies, document counterion, lot-specific purity, and stability under intended storage and assay conditions.

Physical Properties

Item-specific properties from Product Data:

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

Literature/general guidance (not item specifications):

• Physical state: Indole alkaloids of this class are typically obtained as off-white to pale solids or foams after purification, often isolated as free bases or salt forms (e.g., hydrochlorides). Actual appearance depends on form and purity.
• Solubility profile (typical for indole alkaloids):
  • Good: methanol, ethanol, chloroform, dichloromethane, ethyl acetate, acetonitrile (varies with salt/free base).
  • Limited: water for the free base; aqueous solubility increases upon protonation (e.g., with HCl or TFA).
• Acid–base behavior: Presence of a tertiary amine suggests basicity; salts form readily with mineral or organic acids. pKa values for related aspidosperma alkaloids often fall in the range expected for tertiary amines (literature), but a precise pKa for geissoschizoline is not cited here.
• Stability considerations (general): Sensitive indole/indolenine chromophores can be light- and air-sensitive; gradual discoloration on prolonged exposure may occur. Store under inert atmosphere and protected from light when possible.

Quantitative constants (BP/MP, density, logP, refractive index): Not specified for this item; refer to CoA/Spec Sheet. If needed for method development, consult primary literature or request analytical data.

Quality and Grades

Item-specific quality details:

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

Guidance on interpreting quality for this class of product (general):

• Natural product reference standards: For analytical or discovery use, typical documentation includes NMR, HRMS, HPLC/UPLC purity, and sometimes optical rotation. When comparing across lots, align on counterion (free base vs salt) and hydration/solvent of crystallization.
• HPLC/UPLC purity: High-purity material (>95% area by UV) is often preferred for biological assays or as analytical standards. UV cutoff and baseline behavior depend on the indole chromophore.
• Residual solvents/water: Natural products can retain solvents; Karl Fischer and residual solvent profiles are often reported on the CoA. For this item, specific limits are not provided here.
• Stabilizers: None indicated in Product Data. If stabilizers or acid additives (e.g., 0.1% TFA) are present to improve stability/solubility, they will be listed on the CoA.
• Identity confirmation: Vendors typically provide 1H/13C NMR and HRMS. For stereochemically defined alkaloids, optical rotation and chiro-HPLC may be provided.

Recommendation: For critical applications (e.g., quantitative LC–MS), request the CoA and, if needed, a lot-specific spectrum package to confirm identity, purity, and counterion form for Geissoschizoline.

Reaction and Applications

Manufacturer Applications: Not specified beyond general research use.

General research applications for geissoschizine-type indole alkaloids (literature-based, not item-specific):

• Reference standard and probe:
  • Used as a phytochemical reference in method development (HPLC/LC–MS) for Apocynaceae chemotaxonomy and metabolomics.
• Semisynthetic derivatization:
  • N-oxidation of tertiary amine (e.g., m-CPBA) followed by rearrangements enables access to related alkaloid scaffolds.
  • Electrophilic aromatic substitution on the indole ring (e.g., halogenation, nitration under controlled conditions) to generate SAR libraries.
  • Reductive alkylation/acylation at the tertiary amine to modulate basicity and lipophilicity.
• Photophysics/analytics:
  • Indole chromophore provides UV absorbance (typically 220–290 nm); useful for UV detection in chromatographic methods.
• Extraction/purification studies:
  • Model compound for SPE method optimization (cation-exchange vs reversed-phase) due to its protonatable nitrogen.

Practical notes:

• Protect from strong oxidants unless purposeful; the indole can undergo rapid oxidation.
• For basic compounds, add 0.1–1% Et3N in normal-phase eluents to reduce tailing and improve recovery.
• In RP-HPLC, 0.05–0.1% formic acid or TFA commonly sharpens peaks; formic acid is preferable for MS detection.
• If stereochemistry is critical, use chiral stationary phases or derivatize to diastereomeric salts for resolution.

Reaction Conditions

General literature guidance for transformations on indole alkaloids (not item-specific; adjust to your substrate and scale):

• N-oxidation of tertiary amine:
  • Reagents: m-CPBA (1.0–1.5 equiv) in DCM or CH2Cl2/MeOH at 0 °C to RT.
  • Notes: Control temperature to limit over-oxidation; N-oxides can enable rearrangements under thermal or Lewis acid conditions.
• Electrophilic aromatic substitution on indole:
  • Halogenation: NBS or NCS in DMF/MeCN at 0–25 °C for selective C-3 or C-2 substitution depending on conditions.
  • Formylation: Vilsmeier–Haack (POCl3/DMF) at 0–50 °C affords 3-formyl derivatives.
• Reductive amination/quaternization:
  • Reductive amination with aldehydes/ketones using NaBH(OAc)3 in DCE/MeOH at RT; quaternization via alkyl halides in acetonitrile with mild heating.
• Protection strategies:
  • Indole N-protection (if N–H present in a related scaffold) via Boc2O or tosylation; for tertiary amines, carbamate formation or salt formation may be used to modulate reactivity.
• Purification:
  • Use basic modifiers (0.1–1% Et3N) in normal-phase to reduce tailing; for RP-HPLC, water/MeCN with 0.05–0.1% formic acid.

These conditions are representative for the class; specific reactivity of Geissoschizoline may differ. Always run small-scale trials and monitor by TLC/LC–MS/NMR.

Safety and Handling

Authoritative safety data for this product are not specified in the provided Product Data. Always consult the product-specific SDS before use.

Item-specific safety entries:

• Signal word: Not specified for this item; refer to SDS.
• H-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 handling guidance for indole alkaloids (not item-specific):

• Potential hazards: Many natural alkaloids can exhibit bioactivity; avoid inhalation, ingestion, and skin contact. Work in a chemical fume hood.
• PPE: Lab coat, nitrile gloves, splash goggles; upgrade PPE if large quantities or aerosols/dusts are possible.
• Engineering controls: Use a fume hood; avoid open handling of powders. For weighing, use anti-static measures.
• Incompatibilities: Strong oxidizers may react with indole/tertiary amine functionality. Avoid strong bases/acids unless forming salts intentionally. Prevent extended exposure to light and air.
• First aid (general):
  • Skin/eye contact: Remove contaminated clothing, rinse with water for at least 15 minutes; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; obtain medical advice if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spill response: Avoid dust formation; collect with inert absorbent, place in suitable waste container. Decontaminate surfaces with appropriate solvent and detergent.
• Waste: Dispose according to institutional and local regulations for organic, potentially bioactive compounds.

Solvent Selection

Applicability: Geissoschizoline is a small-molecule indole alkaloid; solvent choice is relevant for dissolution, purification, and derivatization.

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

• Polarity and acid–base considerations:
  • Free base form: Higher solubility in moderately polar organics (MeOH, EtOH, MeCN, CHCl3, DCM, EtOAc); limited water solubility.
  • Protonated salts: Enhanced aqueous solubility in mildly acidic aqueous media (e.g., 0.1–1% HCl, AcOH, or TFA).
• Dielectric/miscibility:
  • MeOH (ε ~33, protic) and MeCN (ε ~37, aprotic) dissolve indole alkaloids well and are LC–MS compatible.
  • CHCl3/DCM useful for normal-phase extraction and flash purification; pair with MeOH or i-PrOH modifiers when needed.
• Chromatography:
  • Normal-phase: Hexanes/EtOAc or DCM/MeOH with 0.1–1% Et3N can suppress tailing of basic analytes.
  • Reversed-phase: Water/MeCN or Water/MeOH with 0.1% formic acid or TFA improves peak shape and ionization.
• Sample prep tips:
  • If forming salts to aid solubility, consider volatility of the acid (TFA) for easier removal, mindful of potential TFA adducts in MS.
  • Filter solutions (0.2 µm PTFE/nylon) before HPLC.

Brief comparison (general):

• MeOH: strong solvency, protic; may promote side reactions in strong acids.
• MeCN: LC–MS friendly, aprotic; lower proticity can be advantageous for base-sensitive analytes.
• DMSO: maximal solvency for stocks; high boiling point may complicate removal.

Storage and Reconstitution

Item-specific instructions from Product Data:

• Storage Conditions: Store at -20°C.
• Shipped In: Ice chest + Ice pads.

Additional handling guidance (general, not item-specific):

• Protect from light and moisture. For long-term storage, keep tightly sealed under inert gas (argon or nitrogen) when feasible.
• If provided as a solid: Allow vial to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation.
• If provided in solution: Verify solvent and concentration on the label/CoA. Store as directed; avoid repeated freeze–thaw cycles by aliquoting upon receipt.
• Reconstitution suggestions:
  • Dissolve in dry methanol, acetonitrile, ethanol, or DMSO to prepare stock solutions. For aqueous work, consider forming a dilute acid salt (e.g., 0.1% HCl or TFA) to enhance solubility, then dilute into buffer while avoiding high final organic content if incompatible with the assay.
• Stability monitoring:
  • Periodically assess by LC–MS or HPLC for degradation products, especially after prolonged storage or multiple thaw cycles.

Note: For lot-specific solubility, counterion form, and purity, consult the CoA/Spec Sheet. Research use only.

Structure and Identity

• Item-specific identifiers from Product Data:
  • CAS: 18397-07-4
  • SKU: G1445768
  • 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.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• Structural class (general literature):
  • Geissoschizoline is described in the literature as a monoterpenoid indole alkaloid, typically of the aspidospermane/geissoschizine-type scaffold. Such frameworks feature a fused polycyclic system incorporating an indole (or indolenine) substructure and a tertiary amine.
• 2D structural features (general, literature-based description):
  • Core indole/indolenine ring system fused to multiple alicyclic rings, with at least one tertiary nitrogen (basic center). Stereocenters are commonly present in this alkaloid family; specific absolute configuration for this item is not specified in the Product Data.
• Isomerism and stereochemistry:
  • Many geissoschizine-type natural products possess defined stereochemistry arising from biosynthesis; for this listing, stereochemical assignment is not specified; consult CoA/Spectra if needed.
• Synonymy/context (literature):
  • Isolated from Apocynaceae species; frequently co-occurs with related indole alkaloids in phytochemical studies.

Note: Where exact identifiers (SMILES, InChIKey, exact stereochemistry) are required for cheminformatics, please obtain them from the CoA/Spec Sheet for this lot.

Synthetic Utility

General synthetic perspective for geissoschizine-type indole alkaloids (literature-based, not item-specific):

• Functional group handles:
  • Tertiary amine: amenable to salt formation, quaternization, N-oxidation (m-CPBA), and reductive alkylation.
  • Indole/indolenine: supports electrophilic substitution, Vilsmeier formylation (to 3-formyl indole variants), halogenation, and metal-catalyzed C–H activation in some cases.
  • Allylic/tertiary centers in the polycyclic scaffold may undergo selective oxidations or rearrangements.
• Retrosynthetic value:
  • Serves as a node for accessing related natural products via late-stage functionalization and skeletal rearrangements (Polonovski-type, Wagner–Meerwein-like after N-oxide formation).
• Derivatization strategies:
  • Carbamate/amide formation on available amine functionality to modulate physicochemical properties.
  • Installation of reporter tags (e.g., dansylation or isothiocyanate conjugation) for analytical detection, provided nucleophilic sites are accessible.
• Chiral considerations:
  • If stereochemistry is defined, enantiospecific transformations should preserve configuration; use mild conditions and consider chiral chromatography for resolution if needed.

Use cases:

• As a reference substrate to probe oxidation chemistries on indole alkaloids.
• As a scaffold for SAR libraries by site-selective electrophilic substitution or N-modification.

Target Specificity

Not applicable. This product is a small-molecule alkaloid, not a biological targeting reagent (e.g., antibody, ligand with validated target panel). No antigen, clone, epitope, or species reactivity information is provided or expected for this item.

Domande frequenti

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 18397-07-4, the molecular formula is C19H26N2O, and the molecular weight is 298.42 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.