Reserpine

Source and Occurrence of Reserpine

Reserpine

  • Reserpine is extracted from the roots of Rauwolfia serpentina (Indian snakeroot) and Rauwolfia vomitoria.
  • It is an indole alkaloid with antihypertensive and antipsychotic properties.
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Chemical Structure of Reserpine

Isolation

  1. Extraction:

    • Alcoholic Extraction: Dried and powdered Rauwolfia roots are extracted with ethanol or methanol to obtain the alkaloids.
  2. Purification:

    • Acid-Base Extraction:
      • The extract is acidified to convert reserpine into its water-soluble salt.
      • Basification liberates the free base, which is then extracted with an organic solvent like chloroform.
    • Recrystallization: Reserpine is recrystallized from chloroform or ethanol to enhance purity.
  3. Chromatography:

    • Column Chromatography: Using silica gel and appropriate eluent systems to purify reserpine.
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Identification

  • Physical Properties:

    • Appearance: Yellowish crystalline powder.
    • Melting Point: Approximately 190°C.
    • Solubility: Soluble in alcohol, chloroform; insoluble in water.
  • Spectroscopic Techniques:

    • IR Spectroscopy: Identifies functional groups such as indole ring and ester functionalities.
    • NMR Spectroscopy:
      • ¹H NMR: Reveals proton environments specific to the indole moiety and side chains.
      • ¹³C NMR: Confirms the carbon framework of reserpine.
    • Mass Spectrometry: Molecular ion peak at m/z 608 (free base).
  • Chromatographic Techniques:

    • HPLC: For assessing purity and quantification.
    • TLC: Monitoring extraction and purification stages.

Analysis

  1. Quantitative Analysis:

    • HPLC with UV Detection: Primary method for reserpines quantification.
    • Spectrophotometric Methods: Using specific wavelengths corresponding to reserpine’s absorbance.
  2. Quality Control:

    • Ensuring the absence of other indole alkaloids like ajmalicine.
    • Verification via spectral data.
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Applications and Significance of Reserpine

  • Reserpines are used as an antihypertensive agent by depleting catecholamines and serotonin from nerve terminals.
  • It was also employed in psychiatric treatments for its antipsychotic effects, although its use has declined due to side effects.

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