Alkaloids introduction

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Alkaloids introduction

  1. 1. AlkaloidsAlkaloids Definition:Definition: the term “alkaloid” (alkali-like) isthe term “alkaloid” (alkali-like) is commonly used to designate basiccommonly used to designate basic heterocyclic nitrogenous compounds of plantheterocyclic nitrogenous compounds of plant origin that are physiologically activeorigin that are physiologically active..
  2. 2. Deviation from Definition:Deviation from Definition:  Basicity: Some alkaloids are not basic e.g.Basicity: Some alkaloids are not basic e.g. Colchicine, Piperine, Quaternary alkaloids.Colchicine, Piperine, Quaternary alkaloids.  Nitrogen: The nitrogen in some alkaloids isNitrogen: The nitrogen in some alkaloids is not in a heterocyclic ring e.g. Ephedrine,not in a heterocyclic ring e.g. Ephedrine, Colchicine, Mescaline.Colchicine, Mescaline.  Plant Origine: Some alkaloids are derivedPlant Origine: Some alkaloids are derived from Bacteria, Fungi, Insects, Frogs,from Bacteria, Fungi, Insects, Frogs, Animals.Animals.
  3. 3. Classification:Classification:  True (Typical) alkaloidsTrue (Typical) alkaloids that are derivedthat are derived from amino acids and have nitrogen in afrom amino acids and have nitrogen in a heterocyclic ring. e.g Atropineheterocyclic ring. e.g Atropine  ProtoalkaloidsProtoalkaloids that are derived fromthat are derived from amino acids and do not have nitrogen in aamino acids and do not have nitrogen in a heterocyclic ring. e.g Ephedrineheterocyclic ring. e.g Ephedrine  Pseudo alkaloidsPseudo alkaloids that are not derivedthat are not derived from amino acids but have nitrogen in afrom amino acids but have nitrogen in a heterocyclic ring. e.g Caffeineheterocyclic ring. e.g Caffeine  False alkaloidsFalse alkaloids are non alkaloids giveare non alkaloids give false positive reaction with alkaloidalfalse positive reaction with alkaloidal reagents.reagents.
  4. 4. New Definition:New Definition: Alkaloids are cyclicAlkaloids are cyclic organic compounds containingorganic compounds containing nitrogen in a negative state of oxidationnitrogen in a negative state of oxidation with limited distribution among livingwith limited distribution among living organisms.organisms.
  5. 5. Distribution and occurrence:Distribution and occurrence:  Rare in lower plants.Rare in lower plants.  Dicots are more rich in alkaloids thanDicots are more rich in alkaloids than Monocots.Monocots.  Families rich in Alkaloids: Apocynaceae,Families rich in Alkaloids: Apocynaceae, Rubiaceae, Solanaceae andRubiaceae, Solanaceae and Papaveracea.Papaveracea.  Families free from Alkaloids: Rosaceae,Families free from Alkaloids: Rosaceae, LabiataeLabiatae
  6. 6. Distribution in Plant:Distribution in Plant:  All Parts e.g. Datura.All Parts e.g. Datura.  Barks e.g. CinchonaBarks e.g. Cinchona  Seeds e.g. Nux vomicaSeeds e.g. Nux vomica  Roots e.g. AconiteRoots e.g. Aconite  Fruits e.g. Black pepperFruits e.g. Black pepper  Leaves e.g. TobaccoLeaves e.g. Tobacco  Latex e.g. OpiumLatex e.g. Opium
  7. 7. Forms of Alkaloids:Forms of Alkaloids:  Free basesFree bases  Salts with Organic acids e.g.Salts with Organic acids e.g. Oxalic,Oxalic, acetic acidsacetic acids  Salts with inorganic acids e.g.Salts with inorganic acids e.g. HCl, HHCl, H22SOSO44..  Salts with special acids:Salts with special acids: e.g.e.g. Meconic acidMeconic acid in Opiumin Opium Quinic acidQuinic acid inin CinchonaCinchona  Glycosidal form e.g. Solanine inGlycosidal form e.g. Solanine in SolanumSolanum..
  8. 8. Function in PlantsFunction in Plants  They may act asThey may act as protectiveprotective against insectsagainst insects and herbivores due to their bitterness andand herbivores due to their bitterness and toxicity.toxicity.  They are, in certain cases, the finalThey are, in certain cases, the final productsproducts of detoxificationof detoxification ((waste products)waste products)..  Source of nitrogenSource of nitrogen in case of nitrogenin case of nitrogen deficiency.deficiency.  They, sometimes, act asThey, sometimes, act as growth regulatorsgrowth regulators inin certain metabolic systems.certain metabolic systems.  They may be utilized as aThey may be utilized as a source of energysource of energy inin case of deficiency in carbon dioxidecase of deficiency in carbon dioxide assimilation.assimilation.
  9. 9. Nomenclature:Nomenclature: Trivial namesTrivial names should end byshould end by "ine""ine". These names. These names may refer to:may refer to:  TheThe genusgenus of the plant, such as Atropine fromof the plant, such as Atropine from Atropa belladonaAtropa belladona..  The plantThe plant speciesspecies, such as Cocaine from, such as Cocaine from Erythroxylon cocaErythroxylon coca..  TheThe common namecommon name of the drug, such asof the drug, such as Ergotamine from ergot.Ergotamine from ergot.  The name of theThe name of the discovererdiscoverer, such as Pelletierine, such as Pelletierine that was discovered by Pelletier.that was discovered by Pelletier.  TheThe physiological actionphysiological action, such as Emetine that, such as Emetine that acts as emetic, Morphine acts as narcotic.acts as emetic, Morphine acts as narcotic.  A prominentA prominent physical characterphysical character, such as Hygrine, such as Hygrine that is hygroscopic.that is hygroscopic.
  10. 10. Prefixes and suffixes:Prefixes and suffixes: Prefixes:Prefixes:  "Nor-""Nor-" designates N-demethylation or N-demethoxylation,designates N-demethylation or N-demethoxylation, e.g. norpseudoephedrine and nornicotine.e.g. norpseudoephedrine and nornicotine.  "Apo-""Apo-" designates dehydration e.g. apomorphine.designates dehydration e.g. apomorphine.  "Iso-, pseudo-, neo-,"Iso-, pseudo-, neo-, andand epi-"epi-" indicate different types ofindicate different types of isomers.isomers. Suffixes:Suffixes:  "-dine""-dine" designates isomerism as quinidine anddesignates isomerism as quinidine and cinchonidine.cinchonidine.  "-ine""-ine" indicates, in case of ergot alkaloids, a lowerindicates, in case of ergot alkaloids, a lower pharmacological activity e.g. ergotaminine is less potentpharmacological activity e.g. ergotaminine is less potent than ergotamine.than ergotamine.
  11. 11. Physical Properties:Physical Properties: I- Condition:I- Condition:  MostMost alkaloids are crystallinealkaloids are crystalline solidssolids..  Few alkaloids are amorphous solids e.g. emetine.Few alkaloids are amorphous solids e.g. emetine.  SomeSome areare liquidsliquids that are either:that are either: VolatileVolatile e.g. nicotine and coniine, ore.g. nicotine and coniine, or Non-volatileNon-volatile e.g. pilocarpine ande.g. pilocarpine and hyoscine.hyoscine. II- Color:II- Color: TheThe majoritymajority of alkaloids areof alkaloids are colorlesscolorless butbut somesome areare coloredcolored e.g.:e.g.:  Colchicine and berberine are yellow.Colchicine and berberine are yellow.  Canadine is orange.Canadine is orange.
  12. 12. Physical Properties:Physical Properties: III- Solubility:III- Solubility:  BothBoth alkaloidal basesalkaloidal bases and theirand their saltssalts areare soluble in alcoholsoluble in alcohol..  Generally, theGenerally, the basesbases areare soluble in organic solventssoluble in organic solvents andand insoluble in waterinsoluble in water ExceptionsExceptions::  BasesBases soluble in watersoluble in water: caffeine, ephedrine, codeine,: caffeine, ephedrine, codeine, colchicine, pilocarpine and quaternary ammonium bases.colchicine, pilocarpine and quaternary ammonium bases.  BasesBases insoluble or sparingly soluble in certain organicinsoluble or sparingly soluble in certain organic solventssolvents: morphine in ether, theobromine and theophylline in: morphine in ether, theobromine and theophylline in benzene.benzene.  SaltsSalts are usuallyare usually soluble in watersoluble in water and,and, insoluble orinsoluble or sparingly soluble in organic solvents.sparingly soluble in organic solvents. Exceptions:Exceptions:  SaltsSalts insoluble in waterinsoluble in water: quinine monosulphate.: quinine monosulphate.  SaltsSalts soluble in organic solventssoluble in organic solvents: lobeline and apoatropine: lobeline and apoatropine hydrochlorides are soluble in chloroform.hydrochlorides are soluble in chloroform.
  13. 13. IV- Isomerization:IV- Isomerization:  Optically active isomers may show differentOptically active isomers may show different physiological activities.physiological activities.  ll-ephedrine is 3.5 times more active than-ephedrine is 3.5 times more active than dd-ephedrine.-ephedrine.  ll-ergotamine is 3-4 times more active than-ergotamine is 3-4 times more active than dd-ergotamine.-ergotamine.  dd- Tubocurarine is more active than the corresponding- Tubocurarine is more active than the corresponding ll- form.- form.  Quinine (Quinine (ll-form) is antimalarial and its-form) is antimalarial and its dd- isomer- isomer quinidine is antiarrythmic.quinidine is antiarrythmic.  TheThe racemic (racemic (optically inactive)optically inactive) dldl-atropine is-atropine is physiologically active.physiologically active.
  14. 14. Chemical Properties:Chemical Properties: I- Nitrogen:I- Nitrogen:  Primary amines R-NHPrimary amines R-NH22 e.g. Norephedrinee.g. Norephedrine  Secondary amines RSecondary amines R22-NH e.g. Ephedrine-NH e.g. Ephedrine  Tertiary amines RTertiary amines R33-N e.g. Atropine-N e.g. Atropine  Quaternary ammonium salts RQuaternary ammonium salts R44-N e.g-N e.g dd-Tubocurarine-Tubocurarine II- Basicity:II- Basicity:  RR22-NH-NH >> R-NHR-NH22 >> RR33-N-N  Saturated hexacyclic amines is more basic than aromaticSaturated hexacyclic amines is more basic than aromatic amines.amines.
  15. 15. According to basicity Alkaloids are classifiedAccording to basicity Alkaloids are classified into:into:  Weak bases e.g. CaffeineWeak bases e.g. Caffeine  Strong bases e.g. AtropineStrong bases e.g. Atropine  AmphotericAmphoteric * Phenolic Alkaloids e.g. Morphine* Phenolic Alkaloids e.g. Morphine *Alkaloids with Carboxylic groups e.g. Narceine*Alkaloids with Carboxylic groups e.g. Narceine  Neutral alkaloids e.g. ColchicineNeutral alkaloids e.g. Colchicine
  16. 16. III- Oxygen:III- Oxygen:  Most alkaloids contain Oxygen and areMost alkaloids contain Oxygen and are solid in nature e.g. Atropine.solid in nature e.g. Atropine.  Some alkaloids are free from Oxygen andSome alkaloids are free from Oxygen and are mostly liquids e.g. Nicotine, Coniine.are mostly liquids e.g. Nicotine, Coniine.
  17. 17. IV- Stability:IV- Stability:  Effect of heatEffect of heat:: Alkaloids are decomposed by heat, exceptAlkaloids are decomposed by heat, except StrychnineStrychnine andand caffeinecaffeine ((sublimablesublimable).).  Reaction with acids:Reaction with acids: 1- Salt formation.1- Salt formation. 2- Dil acids hydrolyze Ester Alkaloids e.g. Atropine2- Dil acids hydrolyze Ester Alkaloids e.g. Atropine
  18. 18. 3- Conc. acids may cause:3- Conc. acids may cause:  Dehydration:Dehydration: Atropine → ApoatropineAtropine → Apoatropine Morphine → ApomorphineMorphine → Apomorphine  Demethoxylation:Demethoxylation: e.g. Codeinee.g. Codeine
  19. 19.  Effect of Alkalies:Effect of Alkalies: 1- Dil alkalis1- Dil alkalis liberate most alkaloids from their saltsliberate most alkaloids from their salts e.g. NH3.e.g. NH3. 2- They may cause isomerization (racemization) of2- They may cause isomerization (racemization) of alkaloid as the conversion of hyoscyamine toalkaloid as the conversion of hyoscyamine to atropine.atropine. 3- They also can3- They also can form salts with alkaloidsform salts with alkaloids containing a carboxylic groupcontaining a carboxylic group e.g. narceine.e.g. narceine. 4- Strong alkalis:4- Strong alkalis: such as aqueous NaOH and KOHsuch as aqueous NaOH and KOH form salts with phenolic alkaloids.form salts with phenolic alkaloids. 5- Strong alkalis cause hydrolysis of Ester5- Strong alkalis cause hydrolysis of Ester alkaloidsalkaloids (e.g. atropine, cocaine and(e.g. atropine, cocaine and physostigmine) andphysostigmine) and Amide alkaloidsAmide alkaloids ( colchicines).( colchicines). 66- Strong alkalis cause opening of lactone ring.- Strong alkalis cause opening of lactone ring.
  20. 20.  Effect of light and Oxygen:Effect of light and Oxygen: Some alkaloids are unstable when exposed toSome alkaloids are unstable when exposed to light and Oxygen:light and Oxygen: Eserine Rubreserine Oxygen Alkaline solutions Reserpine Decomposition Ergot Alkaloids Lumi Alkaloids (Inactive)
  21. 21. Qualitative test for Alkaloids:Qualitative test for Alkaloids:  Precipitation Reagents:Precipitation Reagents: They are used to:They are used to: 1- Indicate the absence or presence of Alkaloids1- Indicate the absence or presence of Alkaloids 2- Test for complete of extraction2- Test for complete of extraction Disadvantages:Disadvantages: Some non alkaloids interfereSome non alkaloids interfere such as Proteins, lactones, coumarinssuch as Proteins, lactones, coumarins
  22. 22.  Classification of Alkaloidal precipitating agents:Classification of Alkaloidal precipitating agents: 1- Reagents that form double salts:1- Reagents that form double salts: a- Mayer’s Reagent: Potassium Mercuric Iodide.a- Mayer’s Reagent: Potassium Mercuric Iodide. b- Dragendorff’s Reagents: Potassium Iodobismethate.b- Dragendorff’s Reagents: Potassium Iodobismethate. c- Gold Chloride.c- Gold Chloride. 2- Reagents Containing Halogens:2- Reagents Containing Halogens: a- Wagner’s Reagent: Iodine/ Potassium Iodide.a- Wagner’s Reagent: Iodine/ Potassium Iodide. 3-Organic Acids:3-Organic Acids: a- Hager’s Reagent: Picric Acida- Hager’s Reagent: Picric Acid b- Tannic Acid.b- Tannic Acid. 4- Oxygenated High Molecular Weight Acids:4- Oxygenated High Molecular Weight Acids: a- Phosphomolybdic acida- Phosphomolybdic acid b- Phosphotungestic acidb- Phosphotungestic acid c- Silicotungestic Acidc- Silicotungestic Acid
  23. 23.  Colour Reagents:Colour Reagents: 1- Froehd’s Reagent:1- Froehd’s Reagent: Phosphomolybdic acidPhosphomolybdic acid 2- Marqui’s Reagent:2- Marqui’s Reagent: Formaldehyde/ Conc. HFormaldehyde/ Conc. H22SOSO44 3- Mandalin’s Reagent:3- Mandalin’s Reagent: Sulphovanidic acidSulphovanidic acid 4- Erdmann’s Reagent:4- Erdmann’s Reagent: Conc. HNOConc. HNO33/Conc. H/Conc. H22SOSO44 5-5- Mecke's Reagent:Mecke's Reagent: Selenious acid / conc. HSelenious acid / conc. H22SOSO44 6-6- Shaer's Reagent:Shaer's Reagent: Hydrogen peroxide / conc. HHydrogen peroxide / conc. H22SOSO44 7-7- Rosenthaler's Reagent:Rosenthaler's Reagent: Potassium arsenate / conc. HPotassium arsenate / conc. H22SOSO44 8-8- Conc. HNOConc. HNO33
  24. 24. Extraction, Purification and Isolation ofExtraction, Purification and Isolation of Alkaloids from Powdered plantsAlkaloids from Powdered plants  Extraction and purificationExtraction and purification Method I:Method I: The powder is treated with alkalis to liberates the free basesThe powder is treated with alkalis to liberates the free bases that can then be extracted with water immiscible organicthat can then be extracted with water immiscible organic solvents.solvents. Method II:Method II: The powdered material is extracted withThe powdered material is extracted with water or aqueouswater or aqueous alcoholalcohol containingcontaining dilute aciddilute acid.. AlkaloidsAlkaloids are extracted asare extracted as theirtheir saltssalts together with accompanyingtogether with accompanying soluble impuritiessoluble impurities.. Method III:Method III: The powder is extracted with water soluble organic solventsThe powder is extracted with water soluble organic solvents such as MeOH or EtOH which are good solvents for bothsuch as MeOH or EtOH which are good solvents for both salts and free bases.salts and free bases.
  25. 25. Plant material and solvent Extract Concentration Acidified Extract (Alk. as salts) Organic solvent dissove Impurities Acidification Alkalinization Alkaline aqueous layer Organic solvent dissove Alkaloids
  26. 26.  Liberation of the free bases:Liberation of the free bases: Alkalis are used to liberate free bases. Alkalis must be strongAlkalis are used to liberate free bases. Alkalis must be strong enough to liberate free bases. However, choice of strongenough to liberate free bases. However, choice of strong alkalis must be avoided in some cases:alkalis must be avoided in some cases: 1- Ester Alkaloids e.g. Solanaceous Alkaloids1- Ester Alkaloids e.g. Solanaceous Alkaloids 2- Amide Alkaloids e.g. Colchicine2- Amide Alkaloids e.g. Colchicine 3- Phenolic Alkaloids e.g. Morphine3- Phenolic Alkaloids e.g. Morphine 4- Lactone Alkaloids e.g. Pilocarpine4- Lactone Alkaloids e.g. Pilocarpine 5- Fatty Drugs due to saponification and emulsion formation.5- Fatty Drugs due to saponification and emulsion formation.
  27. 27.  NHNH44OH:OH: Most widely used due to many advantages:Most widely used due to many advantages: 1- Strong enough to liberate most of alkaloids1- Strong enough to liberate most of alkaloids from their salts.from their salts. 2- Milder than fixed alkalis so more safe.2- Milder than fixed alkalis so more safe. 3- Volatile so easy to get rid of it.3- Volatile so easy to get rid of it.  Other Alkalis:Other Alkalis: NaNa22COCO33, NaHCO, NaHCO33, Ca(OH), Ca(OH)22, MgO., MgO.
  28. 28.  Extraction of the free bases:Extraction of the free bases:  CHClCHCl33:: Strong solvent can extract most of theStrong solvent can extract most of the alkaloids.alkaloids. Extracts contain more impurities.Extracts contain more impurities. Carcinogenic.Carcinogenic.  Ether:Ether: Gives cleaner Extract but have someGives cleaner Extract but have some disadvantages:disadvantages: 1- High volatility1- High volatility 2- Peroxide formation2- Peroxide formation 3- High water miscibility3- High water miscibility
  29. 29. Volatile AlkaloidsVolatile Alkaloids  The best way for their extraction is steamThe best way for their extraction is steam distillation.distillation.  Plant material + water + Fixed alkaliPlant material + water + Fixed alkali HeatHeat steam containsteam contain alkaloids received inalkaloids received in acidic sloution.acidic sloution.
  30. 30. Purification of the Crude AlkaloidalPurification of the Crude Alkaloidal Fractions:Fractions:  Repeated Acid-Base procedures:Repeated Acid-Base procedures: Render extractRender extract AcidicAcidic, extract with, extract with organic solventorganic solvent (dissolve non alkaloidal(dissolve non alkaloidal impurities),impurities), AlkalinizeAlkalinize and extract againand extract again withwith organic solventsorganic solvents (Dissolve(Dissolve Alkaloids).Alkaloids).  Precipitation with alkaloidal precipitatingPrecipitation with alkaloidal precipitating agent.agent.  Convert to crystalline salts.Convert to crystalline salts.
  31. 31. Separation of Alkaloidal Mixtures:Separation of Alkaloidal Mixtures:  Fractional Crystallization:Fractional Crystallization: Ephedrine & Pseudoephedrine Oxalates Crystallization from water Ephedrine Oxalate Crystals Pseudoephedrine Oxalate Solution
  32. 32. Atropine & Hyoscyamineine Oxalates Crystallization from Acetone/Ether Atropine Oxalate Crystals Hyoscyamine Oxalate Solution
  33. 33.  Preparation of Derivatives:Preparation of Derivatives: Separation of Primary, Secondary and Tertiary Alkaloids.Separation of Primary, Secondary and Tertiary Alkaloids. Mixture + p-toluenesulphonyl chloride Add HCl and filter Filtrate tertiary alkaloids as salt (no reaction with reagent Precipitate SCl O O 1ry alk derivative 2ry alk derivative SR-HN O O SR-N O O R SR-N O OH keto form enol form soluble in alkalis acidic hydrogen insoluble in alkalis NaOH, filter Filtrate Precipitate 1ry alk derivative 2ry alk derivative
  34. 34.  Fractional Liberation:Fractional Liberation: Atropine & Hyoscyamine & Hyoscine the form of HCl salts 1- Alkalinize by NaHCO3 pH 7.5 2- Extract with Ether Ether Hyoscine free base (pKa = 6.2) Aqueous layer Atropine & Hyoscyamine HCl (pKa = 9.3)
  35. 35.  Fractional Distillation:Fractional Distillation: e.g. Separation of Nicotine and Anabasinee.g. Separation of Nicotine and Anabasine  Chromatographic Separation.Chromatographic Separation.
  36. 36. Identification of Alkaloids:Identification of Alkaloids:  Melting pointMelting point  Colour testColour test  Optical RotationOptical Rotation  Microcrystal testMicrocrystal test  HPLC, GC, GC-MSHPLC, GC, GC-MS  UV, IR, NMR, MS.UV, IR, NMR, MS.
  37. 37. Quantitative Determination of Alkaloids:Quantitative Determination of Alkaloids:  Volumetric methods:Volumetric methods:  These are based on reaction of alkaloidal bases withThese are based on reaction of alkaloidal bases with acids (Acid-Base titration).acids (Acid-Base titration). They include:They include:  Aqueous titration:Aqueous titration: This is carried by either:This is carried by either: 1-1- Direct titrationDirect titration of the alcoholic solution of theof the alcoholic solution of the alkaloidal residue with standard acid, oralkaloidal residue with standard acid, or 2-2- Back titrationBack titration by dissolving the residue in aby dissolving the residue in a known amount of standard acid and back titration ofknown amount of standard acid and back titration of residual acid against standard alkali.residual acid against standard alkali.  Non-aqueous titration:Non-aqueous titration: This method is suitable forThis method is suitable for determination of weak bases e.g. Caffeine.determination of weak bases e.g. Caffeine.
  38. 38.  Gravimetric methods:Gravimetric methods: These methods are recommended for determination of:These methods are recommended for determination of: 1- Very weak bases1- Very weak bases which can not be determined bywhich can not be determined by volumetric methods e.g. caffeine and colchicine.volumetric methods e.g. caffeine and colchicine. 2- Mixtures of alkaloids2- Mixtures of alkaloids that are obtained from the samethat are obtained from the same plant but differ greatly in their molecular weight e.g.plant but differ greatly in their molecular weight e.g. Cinchona and Rawolfia alkaloids.Cinchona and Rawolfia alkaloids. They can be performed by either:They can be performed by either: 1- Direct Weighing of the alkaloidal mixtures1- Direct Weighing of the alkaloidal mixtures 2- Precipitation of the total alkaloids and determination of2- Precipitation of the total alkaloids and determination of the weight of the precipitate obtained.the weight of the precipitate obtained. The majorThe major drawbacksdrawbacks of the gravimetric methods are:of the gravimetric methods are: 1- They are insensitive to microamounts of alkaloids.1- They are insensitive to microamounts of alkaloids. 2- They could not be applied in case of thermolabile and2- They could not be applied in case of thermolabile and volatile alkaloids.volatile alkaloids. 3- Lipophilic impurities in the residue are calculated as3- Lipophilic impurities in the residue are calculated as alkaloids.alkaloids.
  39. 39.  Colourimetric Method:Colourimetric Method: e.g. Morphine + NaNOe.g. Morphine + NaNO22/HCl/HCl Ergot + p-dimethylaminobenzaldehydeErgot + p-dimethylaminobenzaldehyde  Spectrophotometric Methods.Spectrophotometric Methods.  Polarimetric Method.Polarimetric Method.  Fluorimetric Method.Fluorimetric Method.  Chromatographic MethodsChromatographic Methods
  40. 40. Classification of AlkaloidsClassification of Alkaloids  Biogenetic.Biogenetic. Based on the biogenetic pathway that form the alkaloids.Based on the biogenetic pathway that form the alkaloids.  Botanical Source.Botanical Source. According to the plant source of alkaloids.According to the plant source of alkaloids.  Type of Amines.Type of Amines. Primary, Secondary, Tertiary alkaloids.Primary, Secondary, Tertiary alkaloids.  Basic Chemical SkeletonBasic Chemical Skeleton
  41. 41.  Phenylalkylamines:Phenylalkylamines: e.g. Ephedrinee.g. Ephedrine  Pyridine and piperidinePyridine and piperidine e.g. lobeline, nicotinee.g. lobeline, nicotine  TropaneTropane e.g. Atropine.e.g. Atropine. CH2 CH CH3 NH2 N N H NCH3 OH
  42. 42.  QuinolineQuinoline e.g.quinine and quinidinee.g.quinine and quinidine  IsoquinolineIsoquinoline e.g. papaverinee.g. papaverine  PhenantherenPhenantheren e.g. Morphinee.g. Morphine N N
  43. 43.  IndoleIndole e.g.ergometrinee.g.ergometrine  ImidazoleImidazole e.g. pilocarpinee.g. pilocarpine  PurinePurine e.g. caffeinee.g. caffeine N H N N N N N N H Purine 1 2 3 4 5 6 7 8 9
  44. 44.  SteroidalSteroidal e.g. Solanum ande.g. Solanum and VeratrumVeratrum alkaloidsalkaloids  TerpenoidTerpenoid e.g. Taxole.g. Taxol

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