Reserpine - Moligand™, 10mM in DMSO , Synaptic vesicular amine transporter inhibitor, CAS No.50-55-5, Synaptic vesicular amine transporter inhibitor

CAS: 50-55-5 Cat. No.: R408290 분자식: C₃₃H₄₀N₂O₉ 분자량: 608.68 Beilstein Registry Number: 102014 EC 번호: 200-047-9 PubChem CID: 5770

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

개요

Information

Reserpine Reserpine is an inhibitor of multidrug efflux pumps, used as an antipsychotic and antihypertensive drug. Reserpine is an inhibitor of the vesicular monoamine transporter 2 (VMAT2).
In vitro

Reserpine inhibits efflux pumps and reduces sparfloxacin, moxifloxacin and ciprofloxacin IC50s and MICs by up to four-fold in 11, 21 and 48 of the 102 unrelated clinical isolates tested.

In vivo

Reserpine (5 mg/kg s.c.) reduces extracellular DA levels to 4% of basal values in intact rats. Reserpine (5 mg/kg s.c.) diminishes L-DOPA (50 mg/kg i.p.)-induced increases in extracellular dopamine levels to 16% of those obtained in denervated animals not pretreated with reserpine in 6-hydroxydopamine-lesioned rats. Reserpine causes a marked depletion of Vasotocin/oxytocin-neu-rophysin-like immunoreactivity (LI) and CRH-L1 in the median eminence of the rat. Reserpine significantly restores performance on the delayed response task in monkeys. Reserpine has little effect on performance of a visual discrimination task, a reference memory task which does not depend on the prefrontal cortex. Reserpine injection (one dose of 1 mg/kg s.c.) every other day for 3 days causes a significant increase in vacuous chewing, tongue protrusion and duration of facial twitching in rats, compared to the control. Reserpine results in a decreased glutamate uptake in the subcortical parts of rats. Reserpine (5 mg/kg) significantly increases vacuous jaw movements, and also reduces rearing behavior in all age groups of rats.
Cell Data

cell lines：Prostate(LNCap,PC3), Cervix(HeLa), Pancreas(ASPC1), Sarcoma(Saos-2)Ovary(OVCAR8), Stomach(NCI-N87), Melanoma(SKMEL3,A431, MALME3M), Colon(Colo205,SW620,HCT116), Breast(SKBR3,MDA-MB-453,MCF7), Lung(NCI-H82,MV522,NCI-H522), etc.

Concentrations：

Incubation Time：

Powder Purity:≥99%

Specifications

동의어

11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester

사양 및 순도

Moligand™, 10mM in DMSO

생화학 및 생리적 메커니즘

Reserpine is an inhibitor of multidrug efflux pumps, used as an antipsychotic and antihypertensive drug. Reserpine is an inhibitor of the vesicular monoamine transporter 2 (VMAT2).

보관 조건

Store at -80°C

배송

Dry ice packs + Cold packs

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등급

Moligand™

작업 유형

INHIBITOR

작동 메커니즘

Synaptic vesicular amine transporter inhibitor

제품 특성

ALogP

4

이름과 식별자

이성체 SMILES

CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC

WGK 독일

3

PubChem CID

5770

UN 번호

3077

포장 그룹

III

분자량

608.68

Beilstein

102014

관련 대상(인간)

ABCB1 Tchem Multidrug resistance protein 1 (0 Activities)

Discover Target: ABCB1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC18A1 Tchem Chromaffin granule amine transporter (1 Activities)

Discover Target: SLC18A1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC18A2 Tclin Synaptic vesicular amine transporter (1 Activities)

Discover Target: SLC18A2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

화학 및 물리적 특성

• 특정 회전[α]: 177° (C=1,DMF)
• 발화점(°F): 22 °C
• 발화점(°C): 22°C

Application Protocols

No vendor-validated application protocols are provided for this SKU.

• Tested applications and dilutions: Not specified for this item; refer to CoA/Spec Sheet.

General preparation for small-molecule screening (literature/practice):

• Prepare a 10–20 mM stock in anhydrous DMSO. Vortex and, if needed, sonicate briefly to ensure complete dissolution.
• Aliquot into amber, low-bind tubes (e.g., 10–50 μL) and store at −80 °C. Avoid repeated freeze–thaw cycles.
• For assay use, dilute into buffer to desired concentration, keeping final DMSO ≤1–2% v/v. Mix thoroughly and inspect for precipitation; filter through 0.22 μm if required.
• Record lot number, stock concentration, and preparation date for traceability.

For analytical calibration uses, prepare serial dilutions in MeOH or ACN (optionally 0.1% formic acid) and store at −20 °C in amber autosampler vials for short-term runs.

Biological Roles

The following describes literature biology of reserpine as a natural product; it is provided for context only and does not constitute medical/clinical guidance.

• Origin: monoterpenoid indole alkaloid isolated from Rauwolfia spp. (e.g., R. serpentina) (literature).
• Molecular features relevant to biology: tertiary amine enables protonation and interaction with acidic residues; aromatic/indole system supports π–π and cation–π contacts; multiple methoxy/ester groups contribute to lipophilicity and membrane partitioning (literature).
• Reported biochemical target: binds to vesicular monoamine transporters (e.g., VMAT), impairing vesicular uptake of monoamines in vitro (literature). This mechanism is commonly leveraged in basic research as a tool compound to modulate monoamine storage in cellular models.
• Assay utility: used as a positive control in transporter binding assays and as a probe to stress-test assay dynamic range and signal stability due to its well-characterized activity profile (literature practice).
• Metabolism/degradation (in vitro considerations): ester hydrolysis can occur; oxidative sensitivity of the indole may produce colored byproducts upon light/air exposure (literature). Protecting from light/oxidants preserves material integrity in biological testing.

Note: Aladdin Scientific supplies this compound strictly for research use only. No claims are made regarding therapeutic use, diagnosis, or any clinical application.

Buffer Applications

Reserpine is not a buffering agent and has very low water solubility, so classic buffer formulations are not applicable.

• Preparing aqueous working solutions (research use):
  • Use a co‑solvent strategy: pre‑dissolve in DMSO (or ethanol), then dilute into the desired assay buffer (e.g., HEPES, PBS) keeping final co‑solvent ≤1–2% v/v to maintain biological compatibility (general practice).
  • Alternatively, prepare mildly acidic aqueous stocks (e.g., 0.01–0.05 M HCl) to increase solubility via salt formation; verify compatibility with your system and pH targets.
• Filtration: if particulates form upon dilution, pass through a 0.22 μm PTFE or PES filter pre‑rinsed with the same solvent mixture.
• Storage of buffered working solutions: generally prepare fresh; if unavoidable, store short‑term at 2–8 °C protected from light. For long‑term stocks, prefer frozen DMSO aliquots at −80 °C.

For buffer selection (pH control), rely on standard biological buffers (e.g., HEPES pH 7.4, phosphate pH 7.2–7.6); reserpine itself does not provide buffering capacity.

Green Alternatives

While the compound itself is fixed, greener choices can be made in its handling and formulation.

• Preferred solvents for routine operations:
  • Use ethanol or isopropanol instead of chlorinated solvents where solubility allows (trade‑off: lower solubility vs improved EHS profile).
  • DMSO is acceptable for stocks; consider propylene carbonate or PEG‑400 for certain applications where DMSO is restricted (viscosity and assay interference may increase).
• Workup and cleaning:
  • Replace dichloromethane with ethyl acetate for extractions when feasible; monitor for recovery due to solute lipophilicity.
  • Use aqueous ethanol for bench/surface decontamination to reduce volatile organic emissions.

Greener solvent comparison (literature-based, general):

• DMSO: high solvency, low volatility; good EHS profile; may affect some assays at >1–2%.
• Ethanol: renewable, biodegradable; flammable; moderate solvency.
• Ethyl acetate: greener extraction solvent; limited for stock solutions due to volatility/solubility.
• Chlorinated solvents (CHCl3/DCM): excellent solvency but poor EHS; reserve for cases where alternatives fail.

Implementation tips:

• Validate assay performance with greener co‑solvents (e.g., ≤1% ethanol) before full deployment.
• Minimize volumes and adopt microscale additions to limit solvent use.
• Employ amber vials and low‑temperature, short‑path evaporations to reduce degradation and rework.

Pharmaceutical Uses

This product is sold for research use only. The notes below summarize non-clinical, formulation-oriented literature context without implying suitability for therapeutic use.

• Historical context (literature): reserpine has been studied and previously used as an active pharmaceutical ingredient; however, this SKU is not qualified for clinical use.
• Excipient/formulation considerations (research scale):
  • Solubility enhancement by salt formation with mineral acids (e.g., HCl) or by co‑solvent systems (ethanol, propylene glycol) has been described in the literature.
  • Solid-state sensitivity to light and heat suggests amber packaging and desiccation to limit degradation.
• Analytical controls (development context):
  • Stability-indicating methods often rely on reversed-phase HPLC with UV detection around the near‑UV region; LC‑MS is commonly used to track hydrolysis/oxidation products (literature).
• Regulatory status for this item: No pharmacopeial grade is claimed. Not specified for this item; refer to CoA/Spec Sheet.

Any work related to dosage forms, clinical evaluation, or human/animal administration is outside the permitted scope of this product and requires appropriate GMP-grade materials and regulatory oversight.

Physical Properties

Item-specific specs are not provided; values below summarize general literature characteristics of reserpine for planning purposes. Do not treat as acceptance criteria.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: reported ~258–265 °C with decomposition (literature).
• Boiling point: not applicable (decomposes before boiling at ambient pressure) (literature).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable (solid).
• pKa: tertiary amine expected to be weakly basic; reported pKa for the conjugate acid in the ~6–7 range (literature, method-dependent).
• logP (octanol/water): reported in the 3–4 range, consistent with lipophilicity (literature).
• Aqueous solubility: very low in neutral water; increases with acidification (salt formation) or with co-solvents (literature).
• Organic solubility: soluble in DMSO and chloroform; sparingly to moderately soluble in methanol/ethanol; limited in acetonitrile and practically insoluble in alkanes (literature).
• UV/Vis: indole chromophore and trimethoxybenzoyl ester provide π→π* absorption in near-UV; exact λmax is method/solvent dependent (literature).

Important: Where exact numerical specifications are required for qualification, use the lot-specific CoA/Spec Sheet. Literature properties can vary with salt form, hydration, and assay conditions.

Quality and Grades

• Supplied grade: Moligand™ (screening library/ligand-discovery quality). This designation indicates material curated for small‑molecule screening and ligand discovery workflows, emphasizing reliable identity and suitability for assay preparation rather than application-specific pharmacopeial compliance.
• Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Assay/ID controls typically associated with Moligand™ listings (general guidance):
  • Structure confirmation by NMR and/or HRMS.
  • Purity verification by HPLC/UPLC with UV or MS detection.
  • Lot traceability and barcoded vials for library management.
• Stabilizers/inhibitors: None stated. Not specified for this item; refer to CoA/Spec Sheet.
• UV cutoffs, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.
• What this means for users:
  • Suitable for biochemical assays, target binding studies, and reference controls in screening cascades.
  • If your application requires quantitative reference standard certification (e.g., compendial, isotope dilution, or stability‑indicating certificates), request the lot CoA or consider analytical/reference‑standard grades.
• Documentation: For acceptance criteria (purity %, residual solvents, identity spectra), always rely on the lot‑specific CoA/Spec Sheet accompanying this SKU.

Reaction and Applications

This SKU is positioned primarily as a screening/ligand discovery compound; synthetic transformations on reserpine are specialized. The following guidance distinguishes common research uses from advanced derivatizations.

• Research/screening uses (non-clinical):
  • Reference ligand/control compound in biochemical and cell‑free assay panels (literature practice for natural product tool compounds).
  • Analytical system suitability and retention marker for LC‑MS method development involving indole alkaloids.
• Sample handling for assays:
  • Prepare 5–20 mM DMSO stocks, protect from light, and aliquot at −80 °C. Thaw on ice; dilute into assay buffer with ≤1–2% DMSO final.
• Derivatization chemistry (literature context):
  • Ester hydrolysis/transesterification to access reserpic acid derivatives and alternate acyl esters (acidic or basic conditions; monitor to avoid decomposition).
  • O‑demethylation of aryl methoxy groups (e.g., BBr3 or AlCl3 systems) followed by re‑functionalization to probe SAR.
  • N‑oxide formation at the tertiary amine and subsequent Polonovski‑type manipulations as a handle for scaffold modification.
  • Hydrogenation or electrophilic substitutions on the indole motif under carefully controlled conditions.
• Practical notes:
  • Multiple stereocenters and dense functionality demand mild, chemoselective conditions.
  • Protecting groups may be needed to preserve the ester and prevent indole oxidation.
  • Analytical monitoring by HPLC‑DAD and LC‑MS is recommended due to light/acid/base sensitivity.

Reaction Conditions

General, literature-based guidance for common manipulations on reserpine; actual conditions require optimization and rigorous analytical control.

• Ester hydrolysis (to reserpic acid):
  • Mild basic conditions (e.g., K2CO3/MeOH, 0–25 °C) or acidic hydrolysis (e.g., HCl/MeOH). Monitor by HPLC; avoid prolonged exposure that promotes side reactions and demethylation.
• Transesterification/re‑acylation:
  • DCC/DMAP or EDCI/DMAP in CH2Cl2 or EtOAc, 0–25 °C; yields are substrate- and steric‑dependent (literature).
• O‑demethylation (aryl):
  • BBr3 in CH2Cl2 at −78 to 0 °C; quench cautiously. Alternative: AlCl3/thiophenol systems. Protect base‑sensitive moieties.
• N‑oxidation/quaternization:
  • m‑CPBA (N‑oxide) in CH2Cl2, 0–25 °C; or alkyl halides for quaternary ammonium salt formation in acetonitrile/acetone.
• Indole functionalization:
  • Vilsmeier–Haack formylation (POCl3/DMF, −20 to 0 °C) under protection to control regioselectivity; or electrophilic halogenation with NBS under buffered conditions.
• Hydrogenation:
  • Pd/C or PtO2, 1–3 bar H2, alcohol solvent at 0–25 °C; risk of over‑reduction—strict monitoring required.

Common solvents: DCM, DMSO, MeOH/EtOH, EtOAc. Whenever possible, substitute greener options (EtOAc, MeOH) and employ low temperatures and short reaction times to limit degradation.

Note: The molecule is light/acid/base sensitive; apply amber glassware, anhydrous conditions, and minimal headspace oxygen. Reported yields vary widely and are substrate- and route-dependent (literature).

Safety and Handling

• GHS/CLP classification, signal word, and pictograms: Not specified for this item; refer to the SDS for authoritative hazard information.
• General hazards (literature/good practice): complex indole alkaloid; avoid ingestion, inhalation of dust, and skin/eye contact. Handle in a chemical fume hood.
• Light and heat sensitivity: reserpine is known to be light sensitive and may degrade upon prolonged exposure; minimize light and maintain cold chain per storage guidance (literature).
• Incompatibilities: strong oxidizers and strong acids/bases may promote degradation (ester cleavage, oxidation). Avoid reactive acylation/alkylation agents unless intended (general chemistry guidance).
• PPE: lab coat, nitrile gloves, splash goggles; consider double-gloving for extended handling. Use antistatic measures to limit powder aerosolization.
• First aid (overview; defer to SDS):
  • Inhalation: move to fresh air; seek medical evaluation if symptoms persist.
  • Skin: wash with soap and water; remove contaminated clothing.
  • Eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
  • Ingestion: rinse mouth; seek medical attention.
• Spill/cleanup: avoid dust; gently cover with inert absorbent, transfer to waste. Decontaminate surfaces with ethanol or dilute detergent.
• Waste: collect as halogen-free organic solid waste unless otherwise required; follow institutional and local regulations.
• Transport/storage notes: Shipped on dry ice/cold packs. Store at −80 °C as specified in Product Data; keep container tightly closed, desiccated, and protected from light.

Solvent Selection

Reserpine is lipophilic with very low intrinsic water solubility and a basic tertiary amine, favoring dissolution in polar aprotic organics or under acidic conditions.

• Primary stock solvent (screening workflows):
  • DMSO: typically dissolves ≥10 mM with gentle warming/sonication (literature/practice). Stable for aliquoted frozen stocks.
• Alternative solvents:
  • Methanol, ethanol, isopropanol: workable at lower concentrations; useful as co‑solvents for aqueous dosing solutions (literature).
  • Chloroform and dichloromethane: excellent solubility for preparative work; avoid for bioassays and prefer greener options when possible.
  • Acetonitrile: variable solubility; can be used as minor co‑solvent.
• Aqueous formulations:
  • Use co‑solvent (e.g., 0.5–2% DMSO or ethanol) and/or acidify slightly (e.g., 0.01–0.05 M HCl) to form soluble salt for stock solutions; filter if needed (literature guidance). Verify assay compatibility.
• Polarity/miscibility (literature):
  • Polarity class: polar aprotic (for recommended solvents), solute is moderately lipophilic (logP ~3–4).
  • Miscible: DMSO, alcohols; immiscible with alkanes.
• Practical tips:
  • Prepare small, single‑use aliquots to avoid freeze–thaw.
  • Protect from light during dissolution and dispensing.
  • For LC/MS sample prep, prefer MeOH or ACN with 0.1% formic acid to aid ionization; avoid basic eluents that may induce transesterification over time.

Storage and Reconstitution

• Storage conditions (as provided): Store at −80 °C. Shipments are made on dry ice packs + cold packs to maintain the cold chain.
• Container handling:
  • Keep tightly closed, desiccated, and protected from light (amber secondary containment recommended).
  • Minimize headspace and temperature cycling.
• Stability notes (literature/practice): reserpine is light sensitive and may degrade upon exposure to heat, light, or moisture. Maintain at low temperature and prepare small aliquots.

Reconstitution guidelines (research use):

• Solvent: Use anhydrous DMSO for primary stocks (e.g., 10–20 mM). Ethanol or methanol may be used at lower concentrations if compatible with the intended use.
• Procedure:
  1. Allow vial to equilibrate to room temperature in the dark before opening to prevent moisture condensation.
  2. Add pre-warmed solvent (if needed), cap, vortex, and briefly sonicate until fully dissolved.
  3. Dispense single-use aliquots into amber tubes; immediately return unused material to −80 °C.
• Working solutions:
  • Prepare fresh by diluting stock into assay buffer, maintaining final co‑solvent ≤1–2% v/v. If precipitation occurs, adjust co‑solvent or mildly acidify as compatible.
• Freeze–thaw:
  • Avoid repeated freeze–thaw cycles. Thaw aliquots on ice and use promptly; discard any degraded or precipitated solutions.

For definitive stability periods and acceptance criteria, consult the lot-specific CoA/Spec Sheet and SDS.

Structure and Identity

Reserpine is a highly functionalized monoterpenoid indole alkaloid widely used as a small‑molecule reference standard and screening ligand in discovery collections.

• SKU: R408290
• CAS: 50-55-5
• CID (PubChem): 5770
• Grade: Moligand™ (screening library quality)
• Molecular formula: C33H40N2O9 (literature)
• Molecular weight: ~608.69 g/mol (literature)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (descriptive):

• Contains an indole-derived system fused into a polycyclic, oxygenated cage-like framework typical of ajmaline/yohimbine-family alkaloids (literature).
• Functional groups: tertiary amine (basic center), multiple O-methyl ethers, and ester linkages including a 3,4,5‑trimethoxybenzoyl ester (literature).
• Stereochemistry: multiple defined stereocenters across the polycyclic core; exists as a single, well-defined natural stereochemical configuration (literature).
• 2D depiction in words: an indole-like aromatic ring annulated to a multi-ring aliphatic scaffold bearing an internal tertiary amine; several methoxy substituents decorate both the aryl ester and the aliphatic oxygenated rings (literature).

Note: Exact identifiers beyond CAS/CID are not specified in the product data; consult the item’s CoA for definitive line notations.

Synthetic Utility

Reserpine’s dense functionality and defined stereochemistry make it a useful platform for probe development and SAR exploration in natural‑product‑inspired chemistry (literature context).

Key functional elements and reactivity:

• Tertiary amine: amenable to quaternization, N‑oxide formation, or reductive manipulations to tune polarity and binding.
• Ester linkages: hydrolyzable to reserpic acid; re‑esterification enables installation of varied acyl groups (including bioisosteres) for prodrug or probe design (literature).
• Aryl methoxy groups: sites for O‑demethylation followed by diversification (e.g., ether/ester formation) to adjust electronics and H‑bonding.
• Indole motif: electrophilic substitution (e.g., Vilsmeier formylation under protected conditions) or controlled hydrogenation/aromatization sequences.

Retrosynthetic/value:

• Serves as a benchmark scaffold for testing late‑stage functionalization strategies on complex alkaloids.
• A comparator in method development for chemoselective acylation, C–H activation near heteroatoms, and photoredox transformations in polyfunctional settings.

Analytical considerations:

• Use multi-detector HPLC (DAD + MS) to ensure selectivity; degradation can masquerade as partial conversion.
• Protect sensitive positions during harsh steps; prefer orthogonal protection to preserve stereochemical integrity (literature best practices).

Target Specificity

Item-specific target details (e.g., protein target, binding constants, species reactivity) are not provided for this SKU.

• Target/epitope/clone/isotype: Not specified for this item; refer to CoA/Spec Sheet.

General literature context (for orientation only): reserpine is commonly used as a tool compound in studies of vesicular monoamine transporters; however, no binding parameters or selectivity data are specified for this product listing.