alkaloid ppt 5 th sem
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ALKALOIDSALKALOIDS
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• Coined by: Meissner, German Pharmacist (1819)• The term “alkaloid” = alkali-like• Natural origin• 1 or more N atom • Specific Physiological Action
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Classification: True (Typical) alkaloids:
◦ Derived from amino acids◦ Nitrogen in a heterocyclic ring◦ Basic & Toxic ◦ e.g Atropine
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Protoalkaloids:◦ Derived from amino acids◦ Do not have nitrogen in a heterocyclic ring ◦ e.g Ephedrine
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Pseudo alkaloids:◦ Not derived from amino acids◦ Nitrogen in a heterocyclic ring◦ e.g Caffeine
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False alkaloids:◦ Non alkaloids ◦ Give false positive reaction with alkaloidal reagents◦ Eg. Proteins
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Distribution and Occurrence: Rare in lower plants.
Dicots are more rich in alkaloids than Monocots.
Families rich in Alkaloids: Apocynaceae,
Rubiaceae, Solanaceae and Papaveraceae etc. Families free from Alkaloids: Rosaceae,
Labiatae etc.
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Distribution in Distribution in Plant:Plant:
All Parts e.g. Datura.Barks e.g. CinchonaSeeds e.g. Nux vomicaRoots e.g. AconiteFruits e.g. Black pepperLeave e.g. TobaccoLatex e.g. Opium
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Forms of Forms of Alkaloids:Alkaloids:
Free basesSalts with Organic acids e.g. Oxalic, acetic acids
Salts with inorganic acids e.g. HCl, H2SO4.
Salts with special acids: e.g. Meconic acid in Opium Quinic acid in Cinchona
Glycosidal form e.g. Solanine in Solanum.
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Function in Function in PlantsPlants Protective against insects and herbivores
due to their bitterness and toxicity.
The final products of detoxification (waste products).
Source of nitrogen in case of nitrogen deficiency.
Act as growth regulators
Utilized as a source of energy in case of deficiency in carbon dioxide assimilation
Carrier with in plants for transportation
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NomenclatureNomenclature::
Trivial names should end by "ine". These names may refer to:
The genus of the plant◦ Eg. Atropine from Atropa belladona.
The plant species◦ Eg. Cocaine from Erythroxylon coca.
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The common name of the drug◦ Eg. Ergotamine from ergot.
The name of the discoverer◦ Eg. Pelletierine discovered by Pelletier.
The physiological action◦ Eg. Emetine that acts as emetic
A prominent physical character◦ Eg. Hygrine that is hygroscopic.
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Physical Properties: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.
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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
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Physical Physical Properties:Properties:
III- Solubility:Both alkaloidal bases and their salts are
soluble in alcohol.
Generally, the bases are soluble in organic solvents and insoluble in water
Salts are usually soluble in water and, insoluble or sparingly soluble in organic solvents.
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Exceptions:Bases soluble in water: caffeine,
ephedrine, codeine, colchicine, pilocarpine and quaternary ammonium bases.
Bases insoluble or sparingly soluble in certain organic solvents: morphine in ether, theobromine and theophylline in benzene.
Exceptions:Salts insoluble in water: quinine
monosulphate.Salts soluble in organic solvents: lobeline
and apoatropine hydrochlorides are soluble in chloroform.
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IV- IV- Isomerization:Isomerization:
Optically active isomers may show different physiological activities.
l-ephedrine is 3.5 times more active than d-ephedrine.
l-ergotamine is 3-4 times more active than d-ergotamine.
d- Tubocurarine is more active than the corresponding l- form.
Quinine (l-form) is antimalarial and its d- isomer quinidine is antiarrythmic.
The racemic (optically inactive) dl-atropine is physiologically active.
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Chemical Chemical Properties: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.
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According to basicity Alkaloids are According to basicity Alkaloids are classified into:classified into:
Weak bases e.g. Caffeine
Strong bases e.g. Atropine
Amphoteric * Phenolic Alkaloids e.g. Morphine
* Alkaloids with Carboxylic groups e.g.
Narceine
Neutral alkaloids e.g. Colchicine
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III- Oxygen: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.
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IV- Stability:IV- Stability:
Effect of heat: Alkaloids are decomposed by heat
Except: Strychnine and caffeine.
Reaction with acids: 1- Salt formation. 2- Dil acids hydrolyze Ester Alkaloids e.g.
Atropine
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Classification of Alkaloidal precipitating agents:
1- Reagents that form double salts:a- Mayer’s Reagent: Potassium Mercuric Iodide.
b- Dragendorff’s Reagents: Potassium Bismuth Iodide.
c- Gold Chloride.
2- Reagents Containing Halogens:a- Wagner’s Reagent: Iodine/ Potassium Iodide.
3-Organic Acids:a- Hager’s Reagent: Picric Acid
b- Tannic Acid.
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Direct CrystallisationSteam DistillationChromatographic TechniquesGradient pH Technique
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Classification of AlkaloidsClassification of AlkaloidsBiogenetic. Based on the biogenetic pathway that form
the alkaloids.
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Botanical Source.According to the plant source of alkaloids.
Type of Amines.Primary, Secondary, Tertiary alkaloids.
Basic Chemical Skeleton
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Pyridine and Piperidine
Nicotine
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Pyrrole and Pyrrolidine
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Tropane e.g. Atropine, Hyoscine
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Quinoline e.g. Quinine and
Quinidine
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Isoquinoline e.g. Papaverine
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Indole e.g. Ergometrine
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Imidazole e.g. pilocarpine,
Isopilocarpine
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Steroidal e.g. Solanum and
Veratrum alkaloids
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Terpenoide.g. Taxol
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PyrrolizidineEg. Echimidine
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QuinolizidineEg. Lupanine
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Aporphineeg. Boldine
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Proto AlkaloidsProto Alkaloids
◦ Derived from amino acids◦ Do not have nitrogen in a heterocyclic ring
Phenylalkylamines: e.g. Ephedrine
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◦ Not derived from amino acids◦ Nitrogen in a heterocyclic ring Purine
e.g. caffeine
Pseudo AlkaloidsPseudo Alkaloids