Reserpine hydrochloride - 10mM in DMSO , CAS No.16994-56-2

CAS: 16994-56-2 Cat. No.: R654460 分子式: C₃₃H₄₁ClN₂O₉ 分子量: 645.1 PubChem CID: 21155894

GRADE & PURITY 10mM in DMSO

Storage

Protected from light,Desiccated,Store at -80°C

Shipped In

Dry ice packs + Cold packs

概要

Reserpine hydrochloride is an inhibitor of the vesicular monoamine transporter 2 ( VMAT2 ).

In Vitro

Reserpine hydrochloride is an inhibitor of the vesicular monoamine transporter 2 (VMAT2). Reserpine hydrochloride displays a significant on the density of dopamine D1 receptors (F 2,12 =8.81, p<0.01) in the rat striatum. The affinity (Kd) for the dopamine D1 and D2 receptors during withdrawal from acute and chronic administration of reserpine is not change. IC 50 values of 43.9 and 54.9 μM are obtained after 1 day of treatment with Reserpine hydrochloride in JB6 P+ and HepG2-C8 cells, respectively. Reserpine hydrochloride induces luciferase activity in a dose-dependent manner at concentrations ranging from 5 to 50 μM, and no significant induction is observed at concentrations lower than 5 μM. Results demonstrate that Reserpine hydrochloride (2.5 to 10 μM) also increases the protein expression of Nrf2, HO-1, and NQO1. Reserpine hydrochloride at concentrations of 2.5 to 10 μM decreases the mRNA expression of DNMT1, DNMT3a, and DNMT3b in a concentration-dependent manner in JB6 P+ cells after 7 days of treatment. Reserpine hydrochloride at 10 μM generates a significant difference for DNMT3a expression (p<0.05). MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Withdrawal (48 h) from chronic (14-day) but not acute Reserpine hydrochloride administration in a dose of 0.2 mg/kg i.p. produces a significant reduction of the immobility time (F 2,18 =3.68, p<0.05), but increases the climbing time (F 2,18 =4.48, p<0.02), and does not change the swimming time (F 2,18 =1.78; NS) in the forced swim test (FST) in rats . Reserpine hydrochloride at a dose of 5 mg/kg body weight produces significant increase in the urinary excretion profile of vanillylmandelic acid (VMA) compare to control animals. The amount of 5-hydroxyindoleacetic acid (5-HIAA) excreted in animals treated with Reserpine is found to be more than in the control. Dose dependent hypotension is observed with Reserpine hydrochloride. Reserpine hydrochloride at doses of 0.5, 1, 5, 10 and 15 μg/kg produce significant (p<0.01) reduction in blood pressure compare to control. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Assay

JB6 P+ cells are seeded in 96-well plates containing Minimum essential media (MEM) at a density of 1×10 4 cells/mL ( 100 μL/well ) for 1, 3, and 5 days, and HepG2-C8 cells are seeded in plates containing DMEM. After incubation for 24 h, the cells are treated with either DMSO or various concentrations of Reserpine hydrochloride . For JB6 P+ cells, the medium is changed every 2 days for the 3-day and 5-day treatments. Cell viability is assessed using a MTS assay kit according to the manufacturer’s instructions. The absorbance of the formazan product is read at 490 nm, and the cell viability is calculated and compared with the DMSO control group. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

IC50& Target:VMAT2

Specifications

仕様と純度

10mM in DMSO

生化学的・生理学的メカニズム

Reserpine hydrochloride is an inhibitor of the vesicular monoamine transporter 2 ( VMAT2 ).

保管条件

Protected from light,Desiccated,Store at -80°C

入荷

Dry ice packs + Cold packs

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

名前と識別子

異性体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.Cl

PubChem CID

21155894

分子量

645.1

Application Protocols

No tested application protocols are provided for this item.

• Product Data: Recommended dilutions, assay types, or positive controls — Not specified for this item; refer to CoA/Spec Sheet.

General handling suggestions (literature/practice; verify locally):

• Prepare a concentrated stock in anhydrous DMSO; aliquot and freeze to minimize freeze–thaw.
• Immediately before use, dilute into pre-warmed assay buffer or media with vigorous mixing to avoid local supersaturation; maintain low final DMSO percentage consistent with assay tolerance.
• Protect solutions from ambient light and use fresh dilutions to limit degradation.

Always develop assay-specific conditions and validate performance in your system.

Biological Roles

Literature context (non-clinical; for scientific orientation only):

• Chemical class: indole alkaloid (ajmaline/yohimbine family) in hydrochloride salt form.
• Primary molecular activity: high-affinity inhibitor of vesicular monoamine transporters (VMAT), particularly VMAT2, leading to impaired sequestration of monoamines (e.g., dopamine, norepinephrine, serotonin) into synaptic/storage vesicles.
• Consequences in cellular systems: depletion of vesicular monoamine stores, altered quantal release, and modulation of presynaptic neurotransmitter handling; widely used as a tool compound to probe catecholaminergic and serotonergic pathways.
• Broader biochemical insights: affects synaptic vesicle acidification/transport coupling studies, turnover of monoamines, and feedback regulation in neurons and neuroendocrine cells. In peripheral models, it informs studies of chromaffin granule biology and transporter energetics.
• Assay usage: employed as a positive control in uptake assays, transporter binding assays, amperometric release measurements, and imaging of vesicular dynamics.

Note: This description summarizes established literature mechanisms and is provided strictly for research context. SKU R654460 is for research use only. No medical, diagnostic, or therapeutic claims are made or implied.

Buffer Applications

This compound is not a buffering agent and is not used to establish or maintain pH. For experimental use, select buffers based on your biological assay (e.g., phosphate, HEPES, citrate) and ensure compatibility with your planned solvent system (often low-percentage DMSO cosolvent). Maintain mildly acidic to neutral pH to preserve solubility of the hydrochloride salt and avoid free-base precipitation.

Green Alternatives

As a complex bioactive small-molecule salt supplied for research and screening, reserpine hydrochloride is not a process solvent or commodity reagent where greener substitutions are typically evaluated. Green chemistry considerations therefore focus on:

• Solvent choices for handling and solution prep:

  • Prefer water or aqueous buffers when compatible with your assay (maintain mildly acidic pH to preserve solubility), and minimize DMSO percentage while ensuring full dissolution.
  • When organic cosolvent is required, ethanol may be a more benign alternative to aprotic dipolar solvents for short-term handling if solubility allows.

• Waste minimization:

  • Prepare concentrated stocks and aliquot to reduce freeze–thaw cycles and discarded remnants.
  • Scale solutions to immediate needs to limit aged solutions that require disposal.

• Comparison (general; not item-specific):

  • DMSO: excellent solvency but challenging in wastewater; manage via appropriate hazardous waste streams.
  • Ethanol/water: greener profile; may require lower concentrations or acidic pH to avoid precipitation.

Given the compound’s intended use as a reference bioactive, the most impactful green choices lie in solvent reduction, right-sizing experiments, and diligent waste segregation rather than in substituting the compound itself.

Pharmaceutical Uses

This material is provided strictly for research use. It is not supplied as a pharmaceutical excipient and is not intended for human or veterinary use.

• Formulation context (general research handling):
  • For in vitro applications, concentrated DMSO stocks are commonly prepared and diluted into assay media immediately before use.
  • For nonclinical formulation development or device testing, aqueous vehicles may be adjusted slightly acidic to sustain the protonated form and maintain solubility.

Any discussion of historical or clinical use is outside the scope of this product listing and is intentionally omitted. For GMP, pharmacopeial status, or validated manufacturing specifications, consult regulatory references independently; this SKU is for non-GMP research only.

Physical Properties

Only limited item-specific physical data are provided with this listing.

• Item-specific values:

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

• Literature values and general context (for reference; not product specifications):

  • Salt form: hydrochloride of reserpine, typically a solid; many lots are off-white to light-colored and light-sensitive.
  • Solubility (general): improved aqueous solubility versus the free base; readily soluble in polar organic solvents such as DMSO, methanol, ethanol; limited solubility in nonpolar solvents. Water solubility can benefit from slight acidification due to amine protonation.
  • pKa (tertiary amine, literature context for related scaffolds): basic pKa typically in the 7–9 range for protonated tertiary indole alkaloids; exact pKa for this salt not determined here.
  • LogP/logD: the free base is lipophilic; the hydrochloride salt exhibits lower apparent logD at physiological pH due to ionization.
  • Thermal behavior: complex natural-product salts may soften or decompose rather than show a sharp melting point; protect from light and heat.

For authoritative lot-specific values (melting point, water content, identity spectra), consult the product’s CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting grades (general guidance):

  • For small-molecule bioactive salts, common grades include “research grade” or “screening grade,” emphasizing high identity/purity suitable for in vitro/in vivo research models. HPLC or LC–MS purity specifications (e.g., ≥95%) are often used; confirm on the CoA.
  • Low-residual solvent and well-resolved impurity profiles are important due to pharmacological potency; check chromatographic purity, residual solvents (GC), and counterion content (e.g., chloride assay) where available.
  • Stabilizer use: this item lists no stabilizers. If stabilizers or formulating excipients are present in a given lot, they will be disclosed on the CoA and may affect solubility or spectral baselines.

• Identity confirmation (typical methods; general):

  • 1H/13C NMR in DMSO‑d6 or CD3OD, HRMS for exact mass of the protonated cation, chloride confirmation by ion chromatography or argentometric titration, and HPLC/UPLC purity with diode-array detection. Optical rotation may be reported for stereochemical integrity.

For the exact grade, assay method, and acceptance criteria applicable to SKU R654460, please refer to the lot-specific CoA/Spec Sheet.

Reaction and Applications

This compound is primarily a bioactive small molecule standard and library member rather than a synthetic reagent. It is not typically employed as a stoichiometric reagent, catalyst, or solvent in chemical transformations.

• Research applications (general, non-clinical):

  • Used as a reference standard and positive control in transporter biology and neurochemical studies; included in small-molecule screening libraries.
  • Employed in mechanistic studies of vesicular monoamine handling, membrane transport, and storage vesicle biology.

• Synthetic chemistry note:

  • Due to its densely functionalized, stereochemically complex architecture and multiple base/acid-sensitive motifs (tertiary amine salt, esters, methoxy groups), reserpine hydrochloride is generally handled as an analyte rather than modified. Derivatization, when undertaken, requires carefully optimized protecting-group strategies and very mild conditions.

If your objective is synthetic method development, consider simpler indole alkaloid models or the free base form, and consult literature precedents for protecting sensitive ester functions.

Reaction Conditions

Not typically applicable. Reserpine hydrochloride is a complex, sensitive bioactive small molecule that is generally handled as an analyte or standard rather than subjected to synthetic reactions.

• Handling conditions (general good practice):
  • Perform solution preparation at ambient temperature with protection from light.
  • Use anhydrous DMSO or alcohols for stock solutions; avoid strong acids/bases and elevated temperatures that may promote ester cleavage or rearrangement.
  • Maintain mildly acidic conditions if working in aqueous media to keep the amine protonated and the compound in solution.

For any planned chemical modification, consult primary literature for reserpine derivatizations and conduct small-scale feasibility studies under strictly controlled conditions.

Safety and Handling

• GHS/SDS status from Product Data:

  • Signal word: Not specified for this item; refer to SDS.
  • H‑statements: Not specified for this item; refer to SDS.
  • GHS classification and pictograms: Not specified for this item; refer to SDS.

• General laboratory safety guidance (literature/practice; not a substitute for SDS):

  • Reserpine hydrochloride is a potent bioactive indole alkaloid salt; handle as a toxic, pharmacologically active compound. Avoid inhalation, ingestion, and skin contact. Use in a chemical fume hood.
  • PPE: lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Consider double‑gloving for weighing and solution prep.
  • Light sensitivity: protect from light to minimize degradation/epimerization.
  • Incompatibilities: strong oxidizers; strong bases may deprotonate the salt and promote degradation of ester functions. Avoid prolonged exposure to elevated temperatures and moisture.
  • First aid (overview): if skin/eye contact occurs, rinse with water for at least 15 minutes and remove contaminated clothing; if inhaled, move to fresh air; if ingested, seek medical attention. Always follow institutional response procedures.
  • Waste: collect solid and solution waste as halogen‑free organic or pharmaceutical/controlled substance research waste per institutional policy; do not discharge to drain.

Always consult the product SDS for definitive hazard classification, exposure limits, and first‑aid measures.

Solvent Selection

Reserpine hydrochloride is a polar organic salt of a highly oxygenated, lipophilic alkaloid. Solvent choice strongly impacts recovery and solution stability.

• Practical miscibility/solubility (literature/general):

  • Highly soluble: DMSO (preferred for concentrated stocks), DMF, methanol, ethanol.
  • Moderate: water (often improved by slight acidification to maintain protonation and prevent free-base precipitation).
  • Poor: nonpolar solvents (e.g., hexanes, toluene) due to ionic nature of the salt.

• Selection guidance:

  • Screening stocks: prepare in anhydrous DMSO for long-term frozen aliquots; dilute into assay buffer immediately before use.
  • Aqueous work: dissolve first in a minimal volume of DMSO or ethanol, then titrate into buffer with gentle mixing; maintain pH on the acidic side to keep the amine protonated and minimize adsorption to plastics.
  • Avoid strong base and high temperatures, which can promote ester hydrolysis.

• Small comparison (general):

  • DMSO: maximal solubility and stability; hygroscopic, may require desiccated handling.
  • Methanol/Ethanol: convenient for intermediate concentrations; may accelerate transesterification under basic conditions.
  • Water/Buffer: lowest organic content; watch for precipitation upon pH increases.

Confirm solvent and concentration compatibility with your assay system; filter sterilize solutions only if chemically compatible with the membrane material.

Storage and Reconstitution

• Item-specific storage and shipping (from Product Data):

  • Storage conditions: Protected from light, Desiccated, Store at -80°C.
  • Shipped in: Dry ice packs + Cold packs.

• Practical guidance (general best practice; not item-specific specifications):

  • Upon receipt: keep container sealed; allow to equilibrate to room temperature in a desiccator before opening to prevent condensation. The hydrochloride salt form can be hygroscopic; minimize exposure to ambient humidity.
  • Aliquoting: if frequent use is anticipated, consider preparing single-use aliquots as dry powder in amber microvials, or as frozen DMSO stock solutions, to avoid repeated freeze–thaw and light exposure.
  • Reconstitution: dissolve in anhydrous DMSO, methanol, or ethanol; for aqueous use, add the organic stock slowly into buffer with gentle agitation. Maintain mildly acidic pH to preserve solubility.
  • Stability: protect all solutions from light (foil-wrap vials) and store frozen when possible. Discard solutions that show precipitation, discoloration, or unexpected chromatographic profiles.

For definitive shelf-life, retest intervals, and lot-specific stability, consult the CoA/Spec Sheet and SDS for SKU R654460.

Structure and Identity

Reserpine hydrochloride is the protonated hydrochloride salt of the indole alkaloid reserpine, furnishing a cationic tertiary amine with chloride counter‑ion.

• Item-specific identifiers from Product Data:

  • CAS: 16994-56-2
  • CID: 21155894 (PubChem)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • 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.

• Literature/structural context (for orientation; not item-specific specifications):

  • Core scaffold: polycyclic indole (tryptamine-derived) fused to a yohimbine-like framework bearing multiple methoxy substituents.
  • Functional groups: tertiary amine (protonated in the HCl salt), multiple methoxy ethers, ester linkages (including a trimethoxybenzoyl ester), acetal/hemiacetal-like oxygenation pattern.
  • Approximate molecular formula (literature, reserpine HCl): C33H41ClN2O9; MW ≈ 644.8 g/mol.
  • Stereochemistry: multiple defined stereocenters retained from the natural product alkaloid framework.

• 2D structure (described): an indole ring system tethered through an ethylamine chain into a bridged, oxygenated polycyclic ring system; an aromatic trimethoxybenzoyl ester pendant; the tertiary nitrogen is protonated with chloride as counterion.

Synthetic Utility

Reserpine hydrochloride is not typically used as a building block due to its high complexity, multiple sensitive ester linkages, and dense oxygenation pattern. However, in methodological or derivatization studies (literature context):

• Functional group landscape:

  • Tertiary amine (as hydrochloride salt) amenable to salt metathesis, quaternization, or deprotection to the free base under carefully controlled basic conditions.
  • Multiple aryl/alkyl methoxy groups (ether cleavage under strong Lewis/Brønsted acids is generally undesirable for this scaffold).
  • Ester functionality susceptible to hydrolysis or transesterification; any modifications require mild, selective conditions.

• Representative transformations (reported in the context of natural-product chemistry):

  • Conversion between salt and free base to modulate physicochemical properties for analysis.
  • Isotopic labeling (e.g., 2H/13C) on peripheral positions for mechanistic tracing and quantitative analytical standards.
  • Prodrug/ester analog preparation on the acid/ester handle in tightly controlled conditions.

For most laboratories, this compound serves as a reference standard or probe rather than a precursor in multistep synthesis.

Target Specificity

Item-specific target data are not provided for this SKU.

• Product Data: Target, epitope, species reactivity, clone/isotype (where applicable) — Not specified for this item; refer to CoA/Spec Sheet.

• Literature context (for orientation only; not product specification): Reserpine is widely cited as a potent inhibitor of vesicular monoamine transporters (VMAT, especially VMAT2). No guarantee of potency/affinity is implied for this specific item; verify experimentally under your assay conditions.

よくある質問

How should this product be stored?

Store at ?80 °C, protected from light, desiccated. Keep the container tightly closed with desiccant — the material is moisture-sensitive.

How is this product shipped?

This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.

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

The CAS Number is 16994-56-2, the molecular formula is C33H41ClN2O9, and the molecular weight is 645.1 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.