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 Formula: C₃₃H₄₀N₂O₉ Molecular Weight: 608.68 Beilstein Registry Number: 102014 EC Number: 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

Overview

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

Synonyms

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

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

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).

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Synaptic vesicular amine transporter inhibitor

Product Properties

ALogP

4

Names and Identifiers

Isomeric 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 Germany

3

PubChem CID

5770

UN Number

3077

Packing Group

III

Molecular Weight

608.68

Beilstein

102014

Associated Targets(Human)

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)

Chemical and Physical Properties

• Specific Rotation[α]: 177° (C=1,DMF)
• Flash Point(°F): 22 °C
• Flash Point(°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 & 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 & 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 & 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 & 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 & 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.