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Alkaloids:
•These are organic products from natural or synthetic origin which is basic in
nature contains 1 or more nitrogen normally heterocyclic nature possess
specific physiological action on human or animal body in lower dose.
•Alkaloids are generally classified into True alkaloid, Pseudoalkaloid &
Protoalkaloid.
•True alkaloid are generally goes with definition.
•Proto alkaloid contains Nitrogen as heteroatom in side chain of heterocyclic
ring.
Eg: Ephedrine
INTRODUCTION
Pseudoalkaloids are not derived from aminoacids and doesn’t responds to
alkaloidal reagent. Eg: Caffeine.
Properties:
•They are colorless, crystalline but some are amorphous or liquid (nicotine,
coniine) and volatile in nature.
•Some are colored Eg: Betanidin (red) & berberine (yellow).
•If they are free bases (soluble in organic solvents), salt form (soluble in
water), quaternary bases (soluble in water). Caffeine (exists in free base) is
soluble in water because pseudoalkaloid.
•As the alkaloids are basic in nature they are sensitive undergoes
decomposition upon storage.
Caffeine
Ephedrine
Identification Tests:
•Mayers Reagent: Alkaloids are treated with Potassium Mercuric Iodide gives
cream colored precipitate.
•Dragendroff reagent: Alkaloids are treated with Potassium Bismuth Iodide
gives reddish brown colored precipitate.
•Wagners Reagent: Alkaloids are treated with Iodine Potassium Iodide gives
cream colored precipitate.
•Hagers Reagent: Alkaloids are treated with Picric acid gives yellow colored
precipitate.
Extraction of Alkaloids:
•Powdered drug is defatted and treated with alkaline solution (Sodium
carbonate)
•Alkaloid will be free from bases which is extracted with organic solvent like
chloroform & ether.
•It is concentrated and shaken with inorganic acid.
•The organic fraction is subjected for removal of solvent results in crude
alkaloid mixture. Fractional distilled and purified.
•The aqueous fraction containing alkaloidal salts extracted with immiscible
solvents.
Role of alkaloids:
•They are reserved substances of Nitrogen as they supply Nitrogen whenever
needed.
•They are defensive mechanism in plnats
•They are the end products involved in detoxification mechanism.
•The are growth regulatory factors of the plant.
•They conjugates with acid and helps in transport of acid.
Name of the Drug Vinca
Synonym Catharanthus, Periwinkle
Biological Source Dried whole plant – Catharanthus roseus –
Apocynaceae
Geographical
Source
Madgascar, India, US & Europe
Cultivation,
Collection &
Processing
Altitude: 500mtrs
Soil: Light sandy soil
Rainfall: 100cm
Propagation: Seeds
Seeds are sown (Feb)
No need of much water & fertilizers are NPK & FYM
After one year, stem is made cut at base
Whole aerial part is dried
Soil is ploughed around the roots and the roots are
uprooted.
Washed and shade dried
Microscopy
 Upper surface shows rectangular celled epidermis with unicellular covering
trichomes.
 Palisade cells are present beneath upper & lower epidermis.
 Spongy parenchyma with intercellular spaces.
 At midrib presence of collenchyma beneath upper & lower epidermis
 Xylem and phloem is present at center.
 Cruciferous or unequalled or anisocytic stomata is present.
 Calcium oxalate crystals are absent.
Chemical composition & Chemistry
 It is an indole alkaloid.
 It is derived from aminoacid-Tryptophan.
 Vinca alkaloids have asymmetric dimeric chemical structure
composed of 2 basic mulitringed units – an indole nucleus
(Catharanthus) & dihydroindole nucleus (Vindoline).
 Both Vincristine & Vinblastine are identical except for single
substitution on the vindoline nucleus where VCR & VBR possess
formyl & methyl groups respectively.
 The drug is through inhibition of the mitosis at the metaphase stage
of the cell by interaction with the tubuline protein.
Therapeutic uses & Commercial Applications
Anti-neoplastic drug
Myosarcoma
Lymphosarcoma
Antidiabetic
Hypotensive
Commercial application as
Vincristine sulphate: 10-30 µg/kg
Vinblastine sulphate: 100 µg/kg
Name of the Drug Rauwolfia
Synonym Rauwolfia root, Serpentina root, chhotachand,
Sarpagandha
Biological Source Dried roots – Rauwolfia serpentina – Apocynaceae
Geographical
Source
Tropical regions of Asia, America & Africa
Cultivation,
Collection &
Processing
Soil: Clay loamy soil with large amount of humus
pH: 4
Rainfall: 250cm to 500cm
Propagation: Seeds or vegetative.
Seeds are sown (May)
Transplanted in August
Chemical fertilizers(urea & ammoniumsulphate)
3 to 4 years old Uprooted
Washed & Dried
C: greyish yellow – brown
O: OL
T: Bitter
Shape: Subcylindrical, slightly tapering and
tetrastichous
Microscopy
 Cork is made up of stratified cells
followed by phelloderm containing
parenchyma.
 Parenchyma contains starch grains,
few latex cells with resinous matter.
 Secondary phloem contains ca.
Oxalate crystals.
 Xylem consists of vessels & tracheid’s
containing simple or bordered pits.
 Stone cells and phloem fibres are
absent.
Chemical composition & Chemistry:
The major alkaloids are Reserpine and Rescinnamine.
Reserpine:
 Molecular formula is C33H40O9N2.
 M.P is 286-288°C.
 It contains 6 methoxy groups, one tertiary Nitrogen & one NH
group.
 Upon hydrolysis of reserpic acid, trimethoxybenzoic acid &
methanol.
 Reserpic acid contains yohimbine skeleton (Orientation of
pentacyclic system).
 Reserpine is an ester of Reserpic acid having a hydroxyl
group having trimethoxy benzoic acid.
 Reserpine carries an axial attachment of indole moiety to the
piperidine ring.
 Rings C/D & D/E are cis fused.
Reserpine
Rescinnamine:
 Its molecular formula is C35H42N2O9.
 Its melting point is 460 to 462 °F.
 Upon hydrolysis of reserpic acid,
trimethoxycinnamic acid & methanol.
Other alkaloids are -Ajmalicine, Yohimbine,
Ajmaline, Syrosingopine.
Chemical tests
 Fractured surface+ Concentrated HNO3 red colored medullary
rays.
 Reserpine+Vanillin in acetic acid violet red color.
 Rauwolfia+H2SO4 & p-dimethylaminobenzaldehyde (Van Urks
Reagent) violet to red color.
Therapeutic uses & Commercial Applications
•Antihypertensive
•Transquillizer
•Neuropsychiatric disorders
Commercial application as
•Reserpine: 250 µg
•Rescinnamine: 500 µg
Allied drugs and
Substituents
R. caffra, R. Cumminsfi, R. Obscura, R. Rosea & R.
Bombasiana
Name of the Drug Opium
Synonym Raw opium
Biological Source Dried latex – unripened capsule – Papaver somniferum
- Papaveraceae
Geographical Source India, Pakistan & Afghanistan
Cultivation,
Collection &
Processing
Cool weather without freezing temperature and
cloudiness and sufficient sunshine.
Soil: pH: 7
Propagation: Seeds
Seeds were sown
3-4 months bears flowers
Maturity
Capsule turns dark green to light green
Capsules are incised with Nushtur at the depth of
2mm.
Latex oozes out & next day morning dried latex is
scrapped with Charpala.
Further it is processed in Govt factory located in
Ghazipur.
O:Characteristic
T: Bitter
C: Dark brown
Chemical composition &Chemistry
Opium alkaloids derived from Phenylalanine & tyrosine.
The alkaloids are benzylisoquinoline (Narcotine, Narceine, papaverine) &
Phenanthrene type (Morphine, Codeine & Thebaine)
Morphine:
 The chemical formula for morphine is C17H19NO3.
 The three dimensional structure has five rings.
 Of these, three lie approximately in the same plane.
 The other nitrogen-containing ring and the remaining ring are at right
angles to the other three.
All opioid analgesics have some similarities in their structure which
include:
 An aromatic ring
 A quaternary carbon atom linked to a tertiary amine group by two
other carbon atoms
 Morphine also has a methyl group attached to a nitrogen atom.
Other phytoconstituents are Codeine, Narcotine, Papaverine
Codeine
Papaverine
Narcotine
Chemical tests
• Opium + H2O filtered filterate+Fecl3 Deep reddish purple color.
 Morphine sprinkled on HNO3 orange red color (Codeine doesn’t responds).
 Morphine+Potassium ferriccyanide+Fecl3 Bluish green color (Codeine
doesn’t responds).
 Papaverine+Potassium ferriccyanide Lemon yellow color.
Therapeutic uses & Commercial Applications
•Morphine-potent analgesic, sedates respiratory centre hence it produces
respiratory depression and constipation.
•Codeine-relieves local irritation in bronchial tract & antitussive & mild analgesic
effects
•Papaverine- Relaxant effects on smooth muscles on intestine, bronchial tract &
blood vessels.
•Narcotine-Specific depressant action.
Commercial application as
Morphine sulphate: 10 mg
Codeine sulphate: 10-20 mg,
Narcotine: 15mg
Papaverine hydrochloride: 150mg
Allied drugs and Substituents
P. dubium,
P. Orientate,
P. Intermedia,
P. argemone
Synonym Belladona leaf, Deadly night shade leaf
Biological Source Dried leaves-Atropa belladonna-Solanaceae
Geographical Source England & Europeon countires
Cultivation,
Collection &
Processing
Altitude: 1400m above the sea level.
Propagation: Seeds
Seeds sown in May
Urea, potash & Superphosphate is used as fertilizers.
Plant reaches maturity
Leaves and flowering tops were collected
Dried and stored
C: L: Green to browninsh green
O:slight & characteristic
T:bitter
Shape: ovate, acuminate apex, petiolate entire
margin
Atropa
Microscopy
 Epidermis with striated cuticle.
 Anisocytic stomata.
 Uniseriate multicellular covering trichomes
 Glandular tichomes uniseriate with unicellular head.
 Mesophyll with single layer of palisade and spongy parenchyma
containing microsphenoidal calcium oxalate crystals.
Chemical composition &Chemistry
It consists of l-hyoscyamine, a racemic mixture of
Atropine.
Belladonine, Scopoletin, hyoscine.
Atropine:
Its molecular formula is C17H23NO3
Its melting point is 114-116°C.
It consists of tropine and tropic acid moiety.
It is the racemic mixture of L-hyoscyamine & D-
hyoscyamine.
The tropine moiety is synthesized from ornithine &
Tropic acid is synthesized from phenylalanine.
Fusion of pyrrolidine & piperidine ring with common
methylated nitrogen.
Others - Hyoscine
Atropine
Chemical tests
Vitali-Morin Test:
Powder drug+HNO3
Evaporated to dryness +methanolic KOH Acetone solution
Purple color
Therapeutic uses & Commercial Applications
Parasympatholytic drug with anticholinergic properities, Reduces secretions
like saliva, sweat, gastric juices, Strong purgative, Antidote –opium &
chloral hydrate poisoning
Commercial application as Belladonna tincture: 0.6-1 ml
Allied drugs and Substituents
Phytolacca Americana, Solanum nigrum, Ailanthus glandulosa

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UNIT-II PART I.pptx

  • 1. Alkaloids: •These are organic products from natural or synthetic origin which is basic in nature contains 1 or more nitrogen normally heterocyclic nature possess specific physiological action on human or animal body in lower dose. •Alkaloids are generally classified into True alkaloid, Pseudoalkaloid & Protoalkaloid. •True alkaloid are generally goes with definition. •Proto alkaloid contains Nitrogen as heteroatom in side chain of heterocyclic ring. Eg: Ephedrine INTRODUCTION
  • 2. Pseudoalkaloids are not derived from aminoacids and doesn’t responds to alkaloidal reagent. Eg: Caffeine. Properties: •They are colorless, crystalline but some are amorphous or liquid (nicotine, coniine) and volatile in nature. •Some are colored Eg: Betanidin (red) & berberine (yellow). •If they are free bases (soluble in organic solvents), salt form (soluble in water), quaternary bases (soluble in water). Caffeine (exists in free base) is soluble in water because pseudoalkaloid. •As the alkaloids are basic in nature they are sensitive undergoes decomposition upon storage. Caffeine Ephedrine
  • 3. Identification Tests: •Mayers Reagent: Alkaloids are treated with Potassium Mercuric Iodide gives cream colored precipitate. •Dragendroff reagent: Alkaloids are treated with Potassium Bismuth Iodide gives reddish brown colored precipitate. •Wagners Reagent: Alkaloids are treated with Iodine Potassium Iodide gives cream colored precipitate. •Hagers Reagent: Alkaloids are treated with Picric acid gives yellow colored precipitate.
  • 4. Extraction of Alkaloids: •Powdered drug is defatted and treated with alkaline solution (Sodium carbonate) •Alkaloid will be free from bases which is extracted with organic solvent like chloroform & ether. •It is concentrated and shaken with inorganic acid. •The organic fraction is subjected for removal of solvent results in crude alkaloid mixture. Fractional distilled and purified. •The aqueous fraction containing alkaloidal salts extracted with immiscible solvents. Role of alkaloids: •They are reserved substances of Nitrogen as they supply Nitrogen whenever needed. •They are defensive mechanism in plnats •They are the end products involved in detoxification mechanism. •The are growth regulatory factors of the plant. •They conjugates with acid and helps in transport of acid.
  • 5. Name of the Drug Vinca Synonym Catharanthus, Periwinkle Biological Source Dried whole plant – Catharanthus roseus – Apocynaceae Geographical Source Madgascar, India, US & Europe Cultivation, Collection & Processing Altitude: 500mtrs Soil: Light sandy soil Rainfall: 100cm Propagation: Seeds Seeds are sown (Feb) No need of much water & fertilizers are NPK & FYM After one year, stem is made cut at base Whole aerial part is dried Soil is ploughed around the roots and the roots are uprooted. Washed and shade dried
  • 6. Microscopy  Upper surface shows rectangular celled epidermis with unicellular covering trichomes.  Palisade cells are present beneath upper & lower epidermis.  Spongy parenchyma with intercellular spaces.  At midrib presence of collenchyma beneath upper & lower epidermis  Xylem and phloem is present at center.  Cruciferous or unequalled or anisocytic stomata is present.  Calcium oxalate crystals are absent.
  • 7. Chemical composition & Chemistry  It is an indole alkaloid.  It is derived from aminoacid-Tryptophan.  Vinca alkaloids have asymmetric dimeric chemical structure composed of 2 basic mulitringed units – an indole nucleus (Catharanthus) & dihydroindole nucleus (Vindoline).  Both Vincristine & Vinblastine are identical except for single substitution on the vindoline nucleus where VCR & VBR possess formyl & methyl groups respectively.  The drug is through inhibition of the mitosis at the metaphase stage of the cell by interaction with the tubuline protein.
  • 8. Therapeutic uses & Commercial Applications Anti-neoplastic drug Myosarcoma Lymphosarcoma Antidiabetic Hypotensive Commercial application as Vincristine sulphate: 10-30 µg/kg Vinblastine sulphate: 100 µg/kg
  • 9. Name of the Drug Rauwolfia Synonym Rauwolfia root, Serpentina root, chhotachand, Sarpagandha Biological Source Dried roots – Rauwolfia serpentina – Apocynaceae Geographical Source Tropical regions of Asia, America & Africa Cultivation, Collection & Processing Soil: Clay loamy soil with large amount of humus pH: 4 Rainfall: 250cm to 500cm Propagation: Seeds or vegetative. Seeds are sown (May) Transplanted in August Chemical fertilizers(urea & ammoniumsulphate) 3 to 4 years old Uprooted Washed & Dried C: greyish yellow – brown O: OL T: Bitter Shape: Subcylindrical, slightly tapering and tetrastichous
  • 10. Microscopy  Cork is made up of stratified cells followed by phelloderm containing parenchyma.  Parenchyma contains starch grains, few latex cells with resinous matter.  Secondary phloem contains ca. Oxalate crystals.  Xylem consists of vessels & tracheid’s containing simple or bordered pits.  Stone cells and phloem fibres are absent.
  • 11. Chemical composition & Chemistry: The major alkaloids are Reserpine and Rescinnamine. Reserpine:  Molecular formula is C33H40O9N2.  M.P is 286-288°C.  It contains 6 methoxy groups, one tertiary Nitrogen & one NH group.  Upon hydrolysis of reserpic acid, trimethoxybenzoic acid & methanol.  Reserpic acid contains yohimbine skeleton (Orientation of pentacyclic system).  Reserpine is an ester of Reserpic acid having a hydroxyl group having trimethoxy benzoic acid.  Reserpine carries an axial attachment of indole moiety to the piperidine ring.  Rings C/D & D/E are cis fused. Reserpine
  • 12. Rescinnamine:  Its molecular formula is C35H42N2O9.  Its melting point is 460 to 462 °F.  Upon hydrolysis of reserpic acid, trimethoxycinnamic acid & methanol. Other alkaloids are -Ajmalicine, Yohimbine, Ajmaline, Syrosingopine.
  • 13. Chemical tests  Fractured surface+ Concentrated HNO3 red colored medullary rays.  Reserpine+Vanillin in acetic acid violet red color.  Rauwolfia+H2SO4 & p-dimethylaminobenzaldehyde (Van Urks Reagent) violet to red color. Therapeutic uses & Commercial Applications •Antihypertensive •Transquillizer •Neuropsychiatric disorders Commercial application as •Reserpine: 250 µg •Rescinnamine: 500 µg Allied drugs and Substituents R. caffra, R. Cumminsfi, R. Obscura, R. Rosea & R. Bombasiana
  • 14. Name of the Drug Opium Synonym Raw opium Biological Source Dried latex – unripened capsule – Papaver somniferum - Papaveraceae Geographical Source India, Pakistan & Afghanistan Cultivation, Collection & Processing Cool weather without freezing temperature and cloudiness and sufficient sunshine. Soil: pH: 7 Propagation: Seeds Seeds were sown 3-4 months bears flowers Maturity Capsule turns dark green to light green Capsules are incised with Nushtur at the depth of 2mm. Latex oozes out & next day morning dried latex is scrapped with Charpala. Further it is processed in Govt factory located in Ghazipur. O:Characteristic T: Bitter C: Dark brown
  • 15. Chemical composition &Chemistry Opium alkaloids derived from Phenylalanine & tyrosine. The alkaloids are benzylisoquinoline (Narcotine, Narceine, papaverine) & Phenanthrene type (Morphine, Codeine & Thebaine) Morphine:  The chemical formula for morphine is C17H19NO3.  The three dimensional structure has five rings.  Of these, three lie approximately in the same plane.  The other nitrogen-containing ring and the remaining ring are at right angles to the other three.
  • 16. All opioid analgesics have some similarities in their structure which include:  An aromatic ring  A quaternary carbon atom linked to a tertiary amine group by two other carbon atoms  Morphine also has a methyl group attached to a nitrogen atom. Other phytoconstituents are Codeine, Narcotine, Papaverine Codeine Papaverine Narcotine
  • 17. Chemical tests • Opium + H2O filtered filterate+Fecl3 Deep reddish purple color.  Morphine sprinkled on HNO3 orange red color (Codeine doesn’t responds).  Morphine+Potassium ferriccyanide+Fecl3 Bluish green color (Codeine doesn’t responds).  Papaverine+Potassium ferriccyanide Lemon yellow color. Therapeutic uses & Commercial Applications •Morphine-potent analgesic, sedates respiratory centre hence it produces respiratory depression and constipation. •Codeine-relieves local irritation in bronchial tract & antitussive & mild analgesic effects •Papaverine- Relaxant effects on smooth muscles on intestine, bronchial tract & blood vessels. •Narcotine-Specific depressant action.
  • 18. Commercial application as Morphine sulphate: 10 mg Codeine sulphate: 10-20 mg, Narcotine: 15mg Papaverine hydrochloride: 150mg Allied drugs and Substituents P. dubium, P. Orientate, P. Intermedia, P. argemone
  • 19. Synonym Belladona leaf, Deadly night shade leaf Biological Source Dried leaves-Atropa belladonna-Solanaceae Geographical Source England & Europeon countires Cultivation, Collection & Processing Altitude: 1400m above the sea level. Propagation: Seeds Seeds sown in May Urea, potash & Superphosphate is used as fertilizers. Plant reaches maturity Leaves and flowering tops were collected Dried and stored C: L: Green to browninsh green O:slight & characteristic T:bitter Shape: ovate, acuminate apex, petiolate entire margin Atropa
  • 20. Microscopy  Epidermis with striated cuticle.  Anisocytic stomata.  Uniseriate multicellular covering trichomes  Glandular tichomes uniseriate with unicellular head.  Mesophyll with single layer of palisade and spongy parenchyma containing microsphenoidal calcium oxalate crystals.
  • 21. Chemical composition &Chemistry It consists of l-hyoscyamine, a racemic mixture of Atropine. Belladonine, Scopoletin, hyoscine. Atropine: Its molecular formula is C17H23NO3 Its melting point is 114-116°C. It consists of tropine and tropic acid moiety. It is the racemic mixture of L-hyoscyamine & D- hyoscyamine. The tropine moiety is synthesized from ornithine & Tropic acid is synthesized from phenylalanine. Fusion of pyrrolidine & piperidine ring with common methylated nitrogen. Others - Hyoscine Atropine
  • 22. Chemical tests Vitali-Morin Test: Powder drug+HNO3 Evaporated to dryness +methanolic KOH Acetone solution Purple color Therapeutic uses & Commercial Applications Parasympatholytic drug with anticholinergic properities, Reduces secretions like saliva, sweat, gastric juices, Strong purgative, Antidote –opium & chloral hydrate poisoning Commercial application as Belladonna tincture: 0.6-1 ml Allied drugs and Substituents Phytolacca Americana, Solanum nigrum, Ailanthus glandulosa