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Alkaloids
Deepak Kumar Birla
M.Pharm (Pharmacognosy )
Alkaloids
• Definition: the term “alkaloid” (alkali-like)
is commonly used to designate basic
heterocyclic nitrogenous compounds of
plant origin that are physiologically active.
• New Definition: Alkaloids are cyclic
organic compounds containing nitrogen in a
negative state of oxidation with limited
distribution among living organisms.
Classification:
• True (Typical) alkaloids that are derived from
amino acids and have nitrogen in a
heterocyclic ring. e.g Atropine
• Protoalkaloids that are derived from amino
acids and do not have nitrogen in a
heterocyclic ring. e.g Ephedrine
• Pseudo alkaloids that are not derived from
amino acids but have nitrogen in a
heterocyclic ring. e.g Caffeine
Distribution and occurrence:
• Rare in lower plants.
• Dicots are more rich in alkaloids than
Monocots.
• Families rich in Alkaloids: Apocynaceae,
Rubiaceae, Solanaceae and Papaveracea.
• Families free from Alkaloids: Rosaceae,
Labiatae
Distribution in Plant:
• All Parts e.g. Datura.
• Barks e.g. Cinchona
• Seeds e.g. Nux vomica
• Roots e.g. Aconite
• Fruits e.g. Black pepper
• Leaves e.g. Tobacco
• Latex e.g. Opium
Function in Plants
• They may act as protective against insects and
herbivores due to their bitterness and toxicity.
• They are, in certain cases, the final products
of detoxification (waste products).
• Source of nitrogen in case of nitrogen
deficiency.
• They, sometimes, act as growth regulators in
certain metabolic systems.
• They may be utilized as a source of energy in
case of deficiency in carbon dioxide
assimilation.
Physical Properties:
I- Condition:
• Most alkaloids are crystalline solids.
• Few alkaloids are amorphous solids e.g. emetine.
• Some are liquids that are either:
Volatile e.g. nicotine and coniine, or
Non-volatile e.g. pilocarpine and
hyoscine.
II- Color:
The majority of alkaloids are colorless but some are
colored e.g.:
• Colchicine and berberine are yellow.
• Canadine is orange.
• The salts of sanguinarine are copper-red.
III- Solubility:
• Soluble in polar and organic solvent
• In soluble in water
• Salts are usually soluble in water and, insoluble or
sparingly soluble in organic solvents.
IV- Isomerization:
Optically active isomers may show different
physiological activities.
Chemical Properties:
I- Nitrogen:
• Primary amines R-NH2 e.g. Norephedrine
• Secondary amines R2-NH e.g. Ephedrine
• Tertiary amines R3-N e.g. Atropine
• Quaternary ammonium salts R4-N e.g d-
Tubocurarine
II- Basicity:
• R2-NH > R-NH2 > R3-N
• Saturated hexacyclic amines is more basic than
aromatic amines.
III- Oxygen:
• Most alkaloids contain Oxygen and are solid in
nature e.g. Atropine.
• Some alkaloids are free from Oxygen and are
mostly liquids e.g. Nicotine, Coniine
IV- Stability:
• Effect of heat:
Alkaloids are decomposed by heat, except
Strychnine and caffeine (sublimable).
• Reaction with acids:
1- Salt formation.
2. Conc. acids may cause:
• Dehydration:
Atropine → Apoatropine
Morphine → Apomorphine
• Demethoxylation:
e.g. Codeine
Extraction & Isolation of Alkaloids
Plant material and solvent
Extract
Concentration
Acidified Extract (Alk. as salts)
Organic solvent dissove Impurities
Acidification
Alkalinization
Alkaline aqueous layer
Organic solvent dissove Alkaloids
Alkaloids: Classification, Properties and Extraction

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Alkaloids: Classification, Properties and Extraction

  • 2. Alkaloids • Definition: the term “alkaloid” (alkali-like) is commonly used to designate basic heterocyclic nitrogenous compounds of plant origin that are physiologically active. • New Definition: Alkaloids are cyclic organic compounds containing nitrogen in a negative state of oxidation with limited distribution among living organisms.
  • 3. Classification: • True (Typical) alkaloids that are derived from amino acids and have nitrogen in a heterocyclic ring. e.g Atropine • Protoalkaloids that are derived from amino acids and do not have nitrogen in a heterocyclic ring. e.g Ephedrine • Pseudo alkaloids that are not derived from amino acids but have nitrogen in a heterocyclic ring. e.g Caffeine
  • 4. Distribution and occurrence: • Rare in lower plants. • Dicots are more rich in alkaloids than Monocots. • Families rich in Alkaloids: Apocynaceae, Rubiaceae, Solanaceae and Papaveracea. • Families free from Alkaloids: Rosaceae, Labiatae
  • 5. Distribution in Plant: • All Parts e.g. Datura. • Barks e.g. Cinchona • Seeds e.g. Nux vomica • Roots e.g. Aconite • Fruits e.g. Black pepper • Leaves e.g. Tobacco • Latex e.g. Opium
  • 6. Function in Plants • They may act as protective against insects and herbivores due to their bitterness and toxicity. • They are, in certain cases, the final products of detoxification (waste products). • Source of nitrogen in case of nitrogen deficiency. • They, sometimes, act as growth regulators in certain metabolic systems. • They may be utilized as a source of energy in case of deficiency in carbon dioxide assimilation.
  • 7. Physical Properties: I- Condition: • Most alkaloids are crystalline solids. • Few alkaloids are amorphous solids e.g. emetine. • Some are liquids that are either: Volatile e.g. nicotine and coniine, or Non-volatile e.g. pilocarpine and hyoscine. II- Color: The majority of alkaloids are colorless but some are colored e.g.: • Colchicine and berberine are yellow. • Canadine is orange. • The salts of sanguinarine are copper-red.
  • 8. III- Solubility: • Soluble in polar and organic solvent • In soluble in water • Salts are usually soluble in water and, insoluble or sparingly soluble in organic solvents. IV- Isomerization: Optically active isomers may show different physiological activities.
  • 9. Chemical Properties: I- Nitrogen: • Primary amines R-NH2 e.g. Norephedrine • Secondary amines R2-NH e.g. Ephedrine • Tertiary amines R3-N e.g. Atropine • Quaternary ammonium salts R4-N e.g d- Tubocurarine II- Basicity: • R2-NH > R-NH2 > R3-N • Saturated hexacyclic amines is more basic than aromatic amines.
  • 10. III- Oxygen: • Most alkaloids contain Oxygen and are solid in nature e.g. Atropine. • Some alkaloids are free from Oxygen and are mostly liquids e.g. Nicotine, Coniine
  • 11. IV- Stability: • Effect of heat: Alkaloids are decomposed by heat, except Strychnine and caffeine (sublimable). • Reaction with acids: 1- Salt formation. 2. Conc. acids may cause: • Dehydration: Atropine → Apoatropine Morphine → Apomorphine • Demethoxylation: e.g. Codeine
  • 12. Extraction & Isolation of Alkaloids
  • 13. Plant material and solvent Extract Concentration Acidified Extract (Alk. as salts) Organic solvent dissove Impurities Acidification Alkalinization Alkaline aqueous layer Organic solvent dissove Alkaloids