alkaloids introduction
DESCRIPTION
ppt mengenai cara menguji kandungan alkaloidTRANSCRIPT
AlkaloidsAlkaloids
Definition:Definition: the term “alkaloid” (alkali-like) is the term “alkaloid” (alkali-like) is commonly used to designate basic commonly used to designate basic heterocyclic nitrogenous compounds of plant heterocyclic nitrogenous compounds of plant origin that are physiologically activeorigin that are physiologically active..
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 is Nitrogen: 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 derived Plant Origine: Some alkaloids are derived from Bacteria, Fungi, Insects, Frogs, from Bacteria, Fungi, Insects, Frogs, Animals.Animals.
Classification:Classification: True (Typical) alkaloidsTrue (Typical) alkaloids that are derived that are derived
from amino acids and have nitrogen in a from amino acids and have nitrogen in a heterocyclic ring. e.g Atropineheterocyclic ring. e.g Atropine
ProtoalkaloidsProtoalkaloids that are derived from that are derived from amino acids and do not have nitrogen in a amino acids and do not have nitrogen in a heterocyclic ring. e.g Ephedrineheterocyclic ring. e.g Ephedrine
Pseudo alkaloidsPseudo alkaloids that are not derived that are not derived from amino acids but have nitrogen in a from amino acids but have nitrogen in a heterocyclic ring. e.g Caffeineheterocyclic ring. e.g Caffeine
False alkaloidsFalse alkaloids are non alkaloids give are non alkaloids give false positive reaction with alkaloidal false positive reaction with alkaloidal reagents.reagents.
New Definition:New Definition: Alkaloids are cyclic Alkaloids are cyclic organic compounds containing organic compounds containing nitrogen in a negative state of oxidation nitrogen in a negative state of oxidation with limited distribution among living with limited distribution among living organisms.organisms.
Distribution and occurrence:Distribution and occurrence: Rare in lower plants. Rare in lower plants. Dicots are more rich in alkaloids than Dicots are more rich in alkaloids than
Monocots. Monocots. Families rich in Alkaloids: Apocynaceae, Families rich in Alkaloids: Apocynaceae,
Rubiaceae, Solanaceae and Rubiaceae, Solanaceae and Papaveracea.Papaveracea.
Families free from Alkaloids: Rosaceae, Families free from Alkaloids: Rosaceae, LabiataeLabiatae
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
Forms of Alkaloids:Forms of Alkaloids:
Free basesFree bases Salts with Organic acids e.g. Salts with Organic acids e.g. Oxalic, acetic Oxalic, acetic
acidsacids Salts with inorganic acids e.g. Salts with inorganic acids e.g. HCl, HHCl, H22SOSO44..
Salts with special acids: e.g. Salts with special acids: e.g. Meconic acidMeconic acid in Opium in Opium Quinic acidQuinic acid in in CinchonaCinchona
Glycosidal form e.g. Solanine in Glycosidal form e.g. Solanine in SolanumSolanum. .
Function in PlantsFunction in Plants They may act as They may act as protectiveprotective against insects against insects
and herbivores due to their bitterness and and herbivores due to their bitterness and toxicity.toxicity.
They are, in certain cases, the final They are, in certain cases, the final products products of detoxificationof detoxification ( (waste products)waste products). .
Source of nitrogenSource of nitrogen in case of nitrogen in case of nitrogen deficiency.deficiency.
They, sometimes, act as They, sometimes, act as growth regulatorsgrowth regulators in in certain metabolic systems.certain metabolic systems.
They may be utilized as a They may be utilized as a source of energysource of energy in in case of deficiency in carbon dioxide case of deficiency in carbon dioxide assimilation.assimilation.
Nomenclature:Nomenclature:Trivial namesTrivial names should end by should end by "ine""ine". These names . These names
may refer to: may refer to: The The genusgenus of the plant, such as Atropine from of the plant, such as Atropine from
Atropa belladonaAtropa belladona.. The plant The plant speciesspecies, such as Cocaine from , such as Cocaine from
Erythroxylon cocaErythroxylon coca.. The The common namecommon name of the drug, such as of the drug, such as
Ergotamine from ergot.Ergotamine from ergot. The name of the The name of the discovererdiscoverer, such as Pelletierine , such as Pelletierine
that was discovered by Pelletier.that was discovered by Pelletier. The The 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 prominent A prominent physical characterphysical character, such as Hygrine , such as Hygrine
that is hygroscopic.that is hygroscopic.
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 of indicate different types of
isomers. isomers. Suffixes:Suffixes: "-dine" "-dine" designates isomerism as quinidine and designates isomerism as quinidine and
cinchonidine.cinchonidine. "-ine""-ine" indicates, in case of ergot alkaloids, a lower indicates, in case of ergot alkaloids, a lower
pharmacological activity e.g. ergotaminine is less potent pharmacological activity e.g. ergotaminine is less potent than ergotamine.than ergotamine.
Physical Properties:Physical Properties:I- Condition:I- Condition: MostMost alkaloids are crystalline alkaloids are crystalline solidssolids. . Few alkaloids are amorphous solids e.g. emetine. Few alkaloids are amorphous solids e.g. emetine.
Some Some areare liquids liquids that are either: that are either: VolatileVolatile e.g. nicotine and coniine, or e.g. nicotine and coniine, or Non-volatileNon-volatile e.g. pilocarpine and e.g. pilocarpine and
hyoscine.hyoscine.
II- Color:II- Color:The The majoritymajority of alkaloids are of alkaloids are colorlesscolorless but but some some areare
coloredcolored e.g.: e.g.: Colchicine and berberine are yellow. Colchicine and berberine are yellow. Canadine is orange.Canadine is orange. The salts of sanguinarine are copper-red.The salts of sanguinarine are copper-red.
Physical Properties:Physical Properties:III- Solubility:III- Solubility: Both Both alkaloidal basesalkaloidal bases and their and their saltssalts are are soluble in alcoholsoluble in alcohol.. Generally, the Generally, the basesbases are are soluble in organic solventssoluble in organic solvents and and
insoluble in waterinsoluble in water ExceptionsExceptions:: Bases Bases soluble in watersoluble in water: caffeine, ephedrine, codeine, : caffeine, ephedrine, codeine,
colchicine, pilocarpine and quaternary ammonium bases.colchicine, pilocarpine and quaternary ammonium bases. Bases Bases insoluble or sparingly soluble in certain organic insoluble 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 usually are usually soluble in watersoluble in water and, and, insoluble or insoluble or sparingly soluble in organic solvents.sparingly soluble in organic solvents.
Exceptions:Exceptions: Salts Salts insoluble in waterinsoluble in water: quinine monosulphate.: quinine monosulphate. Salts Salts soluble in organic solventssoluble in organic solvents: lobeline and apoatropine : lobeline and apoatropine
hydrochlorides are soluble in chloroform.hydrochlorides are soluble in chloroform.
IV- Isomerization:IV- Isomerization:
Optically active isomers may show different Optically 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. The The racemic (racemic (optically inactive) optically inactive) dldl-atropine is -atropine is
physiologically active.physiologically active.
Chemical Properties:Chemical Properties:
I- Nitrogen:I- Nitrogen: Primary amines R-NHPrimary amines R-NH2 2 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-NH R-NH2 2 >> R R33-N-N
Saturated hexacyclic amines is more basic than aromatic Saturated hexacyclic amines is more basic than aromatic amines.amines.
According to basicity Alkaloids are classified According 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 Amphoteric Amphoteric
* 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
III- Oxygen:III- Oxygen:
Most alkaloids contain Oxygen and are Most alkaloids contain Oxygen and are solid in nature e.g. Atropine.solid in nature e.g. Atropine.
Some alkaloids are free from Oxygen and Some alkaloids are free from Oxygen and are mostly liquids e.g. Nicotine, Coniine.are mostly liquids e.g. Nicotine, Coniine.
IV- Stability:IV- Stability:
Effect of heatEffect of heat::
Alkaloids are decomposed by heat, except Alkaloids are decomposed by heat, except StrychnineStrychnine and and 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
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
Effect of Alkalies:Effect of Alkalies:1- Dil alkalis1- Dil alkalis liberate most alkaloids from their salts liberate most alkaloids from their salts
e.g. NH3. e.g. NH3. 2- They may cause isomerization (racemization) of 2- They may cause isomerization (racemization) of
alkaloid as the conversion of hyoscyamine to alkaloid as the conversion of hyoscyamine to atropine.atropine.
3- They also can 3- They also can form salts with alkaloids form 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 KOH such as aqueous NaOH and KOH form salts with phenolic alkaloids.form salts with phenolic alkaloids.
5- Strong alkalis cause hydrolysis of Ester 5- Strong alkalis cause hydrolysis of Ester alkaloidsalkaloids (e.g. atropine, cocaine and (e.g. atropine, cocaine and physostigmine) and physostigmine) and Amide alkaloidsAmide alkaloids ( colchicines).( colchicines).
66- Strong alkalis cause opening of lactone ring.- Strong alkalis cause opening of lactone ring.
Effect of light and Oxygen:Effect of light and Oxygen:Some alkaloids are unstable when exposed to Some alkaloids are unstable when exposed to
light and Oxygen:light and Oxygen:
Eserine RubreserineOxygen
Alkaline solutions
Reserpine Decomposition
Ergot Alkaloids Lumi Alkaloids(Inactive)
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 interfere Some non alkaloids interfere such as Proteins, lactones, coumarinssuch as Proteins, lactones, coumarins
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
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. H Formaldehyde/ Conc. H22SOSO44
3- Mandalin’s Reagent: 3- Mandalin’s Reagent: Sulphovanidic acidSulphovanidic acid
4- Erdmann’s Reagent:4- Erdmann’s Reagent: Conc. HNO Conc. HNO33/Conc. H/Conc. H22SOSO44
5- 5- Mecke's Reagent:Mecke's Reagent: Selenious acid / conc. H Selenious acid / conc. H22SOSO44
6- 6- Shaer's Reagent:Shaer's Reagent: Hydrogen peroxide / conc. H Hydrogen peroxide / conc. H22SOSO44
7- 7- Rosenthaler's Reagent:Rosenthaler's Reagent: Potassium arsenate / conc. HPotassium arsenate / conc. H22SOSO44
8- 8- Conc. HNOConc. HNO33
Extraction, Purification and Isolation of Extraction, 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 bases The powder is treated with alkalis to liberates the free bases
that can then be extracted with water immiscible organic that can then be extracted with water immiscible organic solvents.solvents.
Method II:Method II: The powdered material is extracted with The powdered material is extracted with water or aqueous water or aqueous
alcoholalcohol containing containing dilute aciddilute acid. . AlkaloidsAlkaloids are extracted as are extracted as their their saltssalts together with accompanying together with accompanying soluble impuritiessoluble impurities..
Method III:Method III: The powder is extracted with water soluble organic solvents The powder is extracted with water soluble organic solvents
such as MeOH or EtOH which are good solvents for both such as MeOH or EtOH which are good solvents for both salts and free bases. salts and free bases.
Plant material and solvent
Extract
Concentration
Acidified Extract (Alk. as salts)
Organic solvent dissove Impurities
Acidification
Alkalinization
Alkaline aqueous layer
Organic solvent dissove Alkaloids
Liberation of the free bases:Liberation of the free bases:
Alkalis are used to liberate free bases. Alkalis must be strong Alkalis are used to liberate free bases. Alkalis must be strong
enough to liberate free bases. However, choice of strong enough 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.
NHNH44OH:OH:
Most widely used due to many advantages:Most widely used due to many advantages:1- Strong enough to liberate most of alkaloids 1- 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.
Extraction of the free bases:Extraction of the free bases: CHClCHCl33::
Strong solvent can extract most of the Strong 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 some Gives cleaner Extract but have some disadvantages:disadvantages:
1- High volatility1- High volatility
2- Peroxide formation2- Peroxide formation
3- High water miscibility3- High water miscibility
Volatile AlkaloidsVolatile Alkaloids
The best way for their extraction is steam The best way for their extraction is steam distillation.distillation.
Plant material + water + Fixed alkaliPlant material + water + Fixed alkali HeatHeat
steam containsteam contain alkaloids received in alkaloids received in
acidic sloution.acidic sloution.
Purification of the Crude Alkaloidal Purification of the Crude Alkaloidal Fractions:Fractions:
Repeated Acid-Base procedures:Repeated Acid-Base procedures:Render extract Render extract AcidicAcidic, extract with , extract with organic solventorganic solvent (dissolve non alkaloidal (dissolve non alkaloidal impurities), impurities), AlkalinizeAlkalinize and extract again and extract again with with organic solventsorganic solvents (Dissolve (Dissolve Alkaloids).Alkaloids).
Precipitation with alkaloidal precipitating Precipitation with alkaloidal precipitating agent.agent.
Convert to crystalline salts.Convert to crystalline salts.
Separation of Alkaloidal Mixtures:Separation of Alkaloidal Mixtures:
Fractional Crystallization:Fractional Crystallization:
Ephedrine & Pseudoephedrine Oxalates
Crystallization from water
Ephedrine OxalateCrystals
Pseudoephedrine OxalateSolution
Atropine & Hyoscyamineine Oxalates
Crystallization from Acetone/Ether
Atropine OxalateCrystals
Hyoscyamine OxalateSolution
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
OSR-N
O
O
R
SR-N
O
OH
keto form
enol form soluble in alkalis
acidic hydrogeninsoluble in alkalis
NaOH, filter
Filtrate Precipitate
1ry alk derivative 2ry alk derivative
Fractional Liberation:Fractional Liberation:
Atropine & Hyoscyamine & Hyoscine the form of HCl salts
1- Alkalinize by NaHCO3 pH 7.52- Extract with Ether
EtherHyoscine free base
(pKa = 6.2)
Aqueous layerAtropine & Hyoscyamine HCl
(pKa = 9.3)
Fractional Distillation:Fractional Distillation:
e.g. Separation of Nicotine and Anabasine e.g. Separation of Nicotine and Anabasine
Chromatographic Separation.Chromatographic Separation.
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.
Quantitative Determination of Alkaloids:Quantitative Determination of Alkaloids:
Volumetric methods:Volumetric methods: These are based on reaction of alkaloidal bases with These 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 of the alcoholic solution of
the alkaloidal residue with standard acid, orthe alkaloidal residue with standard acid, or2- 2- Back titrationBack titration by dissolving the residue in a by dissolving the residue in a
known amount of standard acid and back titration of known 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 for This method is suitable for determination of weak bases e.g. Caffeine.determination of weak bases e.g. Caffeine.
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 by which 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 same that 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 mixtures2- Precipitation of the total alkaloids and determination of 2- Precipitation of the total alkaloids and determination of the weight of the precipitate obtained.the weight of the precipitate obtained.
The major The 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 and 2- They could not be applied in case of thermolabile and volatile alkaloids.volatile alkaloids.3- Lipophilic impurities in the residue are calculated as 3- Lipophilic impurities in the residue are calculated as alkaloids.alkaloids.
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
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
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 NH
NCH3 OH
QuinolineQuinoline
e.g.quinine and quinidinee.g.quinine and quinidine
Isoquinoline Isoquinoline
e.g. papaverinee.g. papaverine
Phenantheren Phenantheren
e.g. Morphinee.g. Morphine
N
N
Indole Indole
e.g.ergometrinee.g.ergometrine
Imidazole Imidazole
e.g. pilocarpinee.g. pilocarpine
Purine Purine
e.g. caffeinee.g. caffeine
NH
N
N
N
N N
N
H
Purine
1
2
34
56 7
8
9
Steroidal Steroidal e.g. Solanum and e.g. Solanum and VeratrumVeratrum
alkaloidsalkaloids
TerpenoidTerpenoide.g. Taxole.g. Taxol