Plant Alkaloids

ALKALOIDSALKALOIDS
Md. Saiful IslamMd. Saiful Islam
Dept. of Pharmaceutical SciencesDept. of Pharmaceutical Sciences
North South UniversityNorth South University
Facebook Group: Pharmacy UniverseFacebook Group: Pharmacy Universe

Alkaloid DefinitionAlkaloid Definition
Alkaloid: Difficult to defineAlkaloid: Difficult to define
No definitive difference betweenNo definitive difference between
an alkaloid and naturallyan alkaloid and naturally
occurring complex amines.occurring complex amines.
Alkaloids:Alkaloids: plant derived, are alkaliplant derived, are alkali
and contain at least one N2-and contain at least one N2-
atom. They also normallyatom. They also normally
have a significant physiologicalhave a significant physiological
action on humans andaction on humans and
animals.animals.
‘‘Proto-alkaloid’/ ‘amino-alkaloid’ –Proto-alkaloid’/ ‘amino-alkaloid’ –
applied to compounds whichapplied to compounds which
lack one or more of thelack one or more of the
properties of typical alkaloids.properties of typical alkaloids.
Other alkaloids which do notOther alkaloids which do not
conform with the generalconform with the general
definition are syntheticdefinition are synthetic
compounds not found in plantscompounds not found in plants
but are very closely related tobut are very closely related to
natural alkaloids.natural alkaloids.

Alkaloid DescriptionAlkaloid Description
Contains nitrogen - usually derived from an aminoContains nitrogen - usually derived from an amino
acid.acid.
 Bitter tasting, generally white solids (exception -Bitter tasting, generally white solids (exception -
nicotine is a brown liquid).nicotine is a brown liquid).
 They give a precipitate with heavy metal iodides.They give a precipitate with heavy metal iodides.

Caffeine, a purine derivative, does not precipitate likeCaffeine, a purine derivative, does not precipitate like
most alkaloids.most alkaloids.
 Alkaloids are basic - they form water solubleAlkaloids are basic - they form water soluble
salts. Most alkaloids are well-defined crystallinesalts. Most alkaloids are well-defined crystalline
substances which unite with acids to form salts.substances which unite with acids to form salts.
In plants, they may existIn plants, they may exist

in the free state,in the free state,

as salts oras salts or

as N-oxides.as N-oxides.
 Occur in a limited number of plants. Nucleic acidOccur in a limited number of plants. Nucleic acid
exists in all plants, whereas, morphine exists inexists in all plants, whereas, morphine exists in
only one plant species.only one plant species.

Tests for AlkaloidsTests for Alkaloids

Most alkaloids are precipitated from neutral or slightlyMost alkaloids are precipitated from neutral or slightly
acidic solution byacidic solution by

Mayer'sMayer's reagent (potassiomercuric iodide solution)reagent (potassiomercuric iodide solution) 
CreamCream coloured precipitate.coloured precipitate.

Dragendorff'sDragendorff's reagent (solution of potassium bismuthreagent (solution of potassium bismuth
iodide)iodide) orangeorange coloured precipitate.coloured precipitate.

Wagner’sWagner’s reagent (iodine in potassium iodide)reagent (iodine in potassium iodide)  red-red-
brownbrown precipitateprecipitate

HagersHagers reagent (picric acid)reagent (picric acid)  yellowyellow precipitateprecipitate

Caffeine does precipitateCaffeine does precipitate

Occurrence, Distribution & LocationOccurrence, Distribution & Location
of Alkaloidsof Alkaloids
Occur in bacteria (Occur in bacteria (PseudomonasPseudomonas
aeruginosaaeruginosa) and rarely in fungi) and rarely in fungi
(pscilocin from hallucinogenic(pscilocin from hallucinogenic
mushrooms).mushrooms).
Some alkaloids occur in severalSome alkaloids occur in several
genera from different speciesgenera from different species
(caffeine), but most occur in(caffeine), but most occur in
closely related species.closely related species.
Some occur in certain familiesSome occur in certain families
(hyoscyamine), while others(hyoscyamine), while others
occur only in a specific speciesoccur only in a specific species
(morphine).(morphine).
Rarely do plants contain moreRarely do plants contain more
than 1 type of alkaloid.than 1 type of alkaloid.
All alkaloids of one plant will haveAll alkaloids of one plant will have
a common biogenenetic origina common biogenenetic origin

Alkaloids occur in all plantAlkaloids occur in all plant
parts, but are usuallyparts, but are usually
localized in one organ (e.g.localized in one organ (e.g.
the bark or seeds).the bark or seeds).
Within the plant, [alkaloid] canWithin the plant, [alkaloid] can
vary widely from part to partvary widely from part to part
– some parts may contain no– some parts may contain no
alkaloids.alkaloids.
Occasionally, different alkaloidsOccasionally, different alkaloids
also form in different parts ofalso form in different parts of
the plant.the plant.
Alkaloid concentrations occur inAlkaloid concentrations occur in
wide ranges – e.g.wide ranges – e.g.
Madagascan periwinkleMadagascan periwinkle
contains 3g per (anti-cancer)contains 3g per (anti-cancer)
alkaloids per tonne of leaves.alkaloids per tonne of leaves.

The Nitrogen of AlkaloidsThe Nitrogen of Alkaloids
The N2 atom can either beThe N2 atom can either be
11º, 2º, 3º or 4ºº, 2º, 3º or 4º
(quaternary).(quaternary).
This N2 feature affects theThis N2 feature affects the
alkaloid derivativesalkaloid derivatives
which can be preparedwhich can be prepared
and the isolationand the isolation
procedures.procedures.

Physical-Chemical Properties ofPhysical-Chemical Properties of
AlkaloidsAlkaloids
MW: 100 – 900MW: 100 – 900
Most bases which do not contain O2 are liquid atMost bases which do not contain O2 are liquid at
room temperature (nicotine), while those that doroom temperature (nicotine), while those that do
are solids. In rare cases they are coloured.are solids. In rare cases they are coloured.
Most solid bases rotate the plane of polarized light,Most solid bases rotate the plane of polarized light,
have high melting points.have high melting points.
Normally are not soluble in water (occasionallyNormally are not soluble in water (occasionally
slightly soluble).slightly soluble).
Soluble in apolar or slightly polar organic solvents.Soluble in apolar or slightly polar organic solvents.
Soluble in concentrated hydroalcoholic solutionsSoluble in concentrated hydroalcoholic solutions

The basicity of alkaloids depends on the availability of theThe basicity of alkaloids depends on the availability of the
lone pair of e- on the N2 atoms: e- donating groupslone pair of e- on the N2 atoms: e- donating groups
enhance basicity, while e-withdrawing groups decreaseenhance basicity, while e-withdrawing groups decrease
it.it.
Because some alkaloids have a carbonyl group on theBecause some alkaloids have a carbonyl group on the
amide, they can also be neutral (colchicine & piperine).amide, they can also be neutral (colchicine & piperine).
Basicity is also influenced by steric constraints.Basicity is also influenced by steric constraints.
Basic characteristic renders complex alkaloids unstable, soBasic characteristic renders complex alkaloids unstable, so
that in solution they are sensitive to heat, light & oxygen.that in solution they are sensitive to heat, light & oxygen.
Basic character of alkaloids also allows them to form saltsBasic character of alkaloids also allows them to form salts
with mineral acids (such as hydrochlorides, nitrates andwith mineral acids (such as hydrochlorides, nitrates and
sulphates) or inorganic acids (tartrates, sulfamates).sulphates) or inorganic acids (tartrates, sulfamates).
Alkaloid salts are soluble in water and dilute alcohols.Alkaloid salts are soluble in water and dilute alcohols.
Solid salts can be conserved well and are a commonSolid salts can be conserved well and are a common
commercial form of alkaloids.commercial form of alkaloids.

Classification of AlkaloidsClassification of Alkaloids
Alkaloids have a large variety in their botanical &Alkaloids have a large variety in their botanical &
biochemical origin, in chemical structure andbiochemical origin, in chemical structure and
pharmaceutical action. Therefore, like flavonoids, apharmaceutical action. Therefore, like flavonoids, a
range of different classification systems exist forrange of different classification systems exist for
grouping alkaloids.grouping alkaloids.
They can therefore be classified according to theirThey can therefore be classified according to their
• Biological originBiological origin
• Chemical structure - 2 divisionsChemical structure - 2 divisions
•
i. Atypical/non-hetrocyclic alkaloids (protoalkaloids ori. Atypical/non-hetrocyclic alkaloids (protoalkaloids or
biological amines)biological amines)
•
ii. Typical/hetrocyclic alkaloids (divided into 14 groupsii. Typical/hetrocyclic alkaloids (divided into 14 groups
according to their ring structure)according to their ring structure)
• Biosynthetic pathwayBiosynthetic pathway

Naming of AlkaloidsNaming of Alkaloids
Numerous methods can be usedNumerous methods can be used
to name alkaloidsto name alkaloids
• Generic plant name – atropineGeneric plant name – atropine
fromfrom Atropa belladonnaAtropa belladonna
• Specific name of the plant –Specific name of the plant –
cocaine fromcocaine from Erythroxylum cocaErythroxylum coca..
• Common name of the herb –Common name of the herb –
ergotamine from ergot (rye)ergotamine from ergot (rye)
• Physiological action of the plantPhysiological action of the plant
– emetine producing emesis– emetine producing emesis
• Other – e.g. morphine derivedOther – e.g. morphine derived
from ancient Greek mythology –from ancient Greek mythology –
Morpheus – god of dreamsMorpheus – god of dreams

Extraction of AlkaloidsExtraction of Alkaloids
Extraction is based on the basicity ofExtraction is based on the basicity of
alkaloids and on the fact that theyalkaloids and on the fact that they
normally occur in plants as salts (i.e.: onnormally occur in plants as salts (i.e.: on
the solubility of bases and salts in waterthe solubility of bases and salts in water
and organic solvents).and organic solvents).
Herbs often contain other materials whichHerbs often contain other materials which
can interfere with extraction such as largecan interfere with extraction such as large
amounts of fat, waxes, terpenes, pigmentsamounts of fat, waxes, terpenes, pigments
and other lipophilic substances (e.g byand other lipophilic substances (e.g by
forming emulsions) – avoided by defattingforming emulsions) – avoided by defatting
the crushed herb (using petroleum etherthe crushed herb (using petroleum ether
and hexane)and hexane)

Alkaloid ExtractionAlkaloid Extraction
Extraction method normallyExtraction method normally
depends on the rawdepends on the raw
material, the purpose ofmaterial, the purpose of
extraction & the scale onextraction & the scale on
which is to be performed.which is to be performed.
For research purposes:For research purposes:
chromatography allowschromatography allows
for quick and reliablefor quick and reliable
results.results.
If larger amounts ofIf larger amounts of
alkaloids need to bealkaloids need to be
extracted, one of theextracted, one of the
following methods can befollowing methods can be
used.used. TLC plateTLC plate

Extraction in an Alkaline MediumExtraction in an Alkaline Medium
Step 1: Powdered, defatted herb is mixed with an alkalineStep 1: Powdered, defatted herb is mixed with an alkaline
aqueous solution.aqueous solution.
This displaced alkaloids from their salt combinations.This displaced alkaloids from their salt combinations.
Free bases are then extracted with organic solvents.Free bases are then extracted with organic solvents.
Normally aqueous ammonia is used, but a carbonateNormally aqueous ammonia is used, but a carbonate
solution is used when alkaloids contain fragile elementssolution is used when alkaloids contain fragile elements
such as a ester or lactone.such as a ester or lactone.
In some cases, e.g. Cinchona bark, a mixture of calciumIn some cases, e.g. Cinchona bark, a mixture of calcium
hydroxide & sodium hydroxide should be used as thehydroxide & sodium hydroxide should be used as the
alkaloids are bound to tannins.alkaloids are bound to tannins.
Organic solvent: chloroform, dichloromethane or ethylOrganic solvent: chloroform, dichloromethane or ethyl
acetate – depends on the toxicity, safety, cost & ease ofacetate – depends on the toxicity, safety, cost & ease of
recovery and recycling of the solvent).recovery and recycling of the solvent).

The Soxhlet ApparatusThe Soxhlet Apparatus
Industry: uses solid-liquidIndustry: uses solid-liquid
extractors based on theextractors based on the
principle of counter-currentprinciple of counter-current
extraction, such Soxhletextraction, such Soxhlet
apparatus.apparatus.

Extraction of Alkaloids: Step IIExtraction of Alkaloids: Step II
Organic solvent containingOrganic solvent containing
alkaloids (bases) is separatedalkaloids (bases) is separated
from residue & concentratedfrom residue & concentrated
by distillation under pressure ifby distillation under pressure if
needed.needed.
Solvent is stirred with an acidicSolvent is stirred with an acidic
aqueous solution: alkaloids goaqueous solution: alkaloids go
into the solution as salts.into the solution as salts.
Impurities remain in theImpurities remain in the
organic phase.organic phase.
Repeated until the organic phaseRepeated until the organic phase
no longer contains alkaloids.no longer contains alkaloids.
Many acids can be used (HCL,Many acids can be used (HCL,
Sulfuric, citric, tartaric), butSulfuric, citric, tartaric), but
always in very dilutealways in very dilute
concentrations (1-5%)concentrations (1-5%)

Alkaloid Extraction: Step IIIAlkaloid Extraction: Step III
Aqueous solution of alkaloid salts isAqueous solution of alkaloid salts is
washed with an apolar solventwashed with an apolar solvent
(hexane)(hexane)
Alkalinized with a base using an organicAlkalinized with a base using an organic
solvent not miscible with water.solvent not miscible with water.
Alkaloids precipitate and dissolve in theAlkaloids precipitate and dissolve in the
organic phase.organic phase.
Extraction of aqueous phase continues tillExtraction of aqueous phase continues till
all alkaloids have moved into theall alkaloids have moved into the
organic phase (tested when Mayer’sorganic phase (tested when Mayer’s
reaction on the aqueous phasereaction on the aqueous phase
becomes negative).becomes negative).
This purification step may be carried outThis purification step may be carried out
in a separation funnel or in centrifugalin a separation funnel or in centrifugal
extractors.extractors.
Separation FunnelSeparation Funnel

Final StepFinal Step
 Organic solventOrganic solvent
containing alkaloid basescontaining alkaloid bases
is decanted, freed fromis decanted, freed from
water traces (drying overwater traces (drying over
anhydrous salt e.g.anhydrous salt e.g.
sodium sulphate) andsodium sulphate) and
evaporated underevaporated under
reduced pressure.reduced pressure.
A dry residue remains: totalA dry residue remains: total
basic alkaloids.basic alkaloids.
Kava PowderKava Powder

Alkaloid Extraction in AcidicAlkaloid Extraction in Acidic
MediumMedium
2 Methods possible2 Methods possible
Pulverized drug is extractedPulverized drug is extracted
directly with acidified waterdirectly with acidified water
OrOr
Pulverized drug is extractedPulverized drug is extracted
with acidified alcoholic or awith acidified alcoholic or a
hydroalcoholic solution.hydroalcoholic solution.
This is then followed byThis is then followed by
distillation under vacuumdistillation under vacuum
(eliminates that alcohol,(eliminates that alcohol,
leaving behind and acidicleaving behind and acidic
aqueous solution of alkaloidaqueous solution of alkaloid
salts)salts) Vacuum DistillationVacuum Distillation

In both cases: Results = aqueous solution ofIn both cases: Results = aqueous solution of
alkaloid salts needing purification.alkaloid salts needing purification.
Purification achieved byPurification achieved by
• Alkalinizing solution & extracting bases with anAlkalinizing solution & extracting bases with an
immiscible organic solvent.immiscible organic solvent.
• Selectively absorb the alkaloids contained in theSelectively absorb the alkaloids contained in the
solution on an ion exchange resin, then elutingsolution on an ion exchange resin, then eluting
them with a strong acid.them with a strong acid.
• Precipitating the alkaloids as iodomercurates.Precipitating the alkaloids as iodomercurates.
The resulting alkaloids are recovered byThe resulting alkaloids are recovered by
filtration, dissolved in a mixture of water, alcoholfiltration, dissolved in a mixture of water, alcohol
and acetone and decomposed by passingand acetone and decomposed by passing
through an ion-exchange resin.through an ion-exchange resin.

Ion-Exchange ResinIon-Exchange Resin

Isolation of AlkaloidsIsolation of Alkaloids
All methods of alkaloidAll methods of alkaloid
extraction yield impureextraction yield impure
compounds, so alkaloidscompounds, so alkaloids
therefore have to betherefore have to be
separated.separated.
TLC and HPLC are mostTLC and HPLC are most
commonly used.commonly used.
Under the best conditions,Under the best conditions,
alkaloids can be obtainedalkaloids can be obtained
by direct crystallization:by direct crystallization:
simply by neutralizing thesimply by neutralizing the
acidic extraction medium.acidic extraction medium.
Crystals of HydrastineCrystals of Hydrastine

Isolation of AlkaloidsIsolation of Alkaloids
Large-scale extractions may be sent to aLarge-scale extractions may be sent to a
factory for purification & separationfactory for purification & separation
(for cinchona and cocoa alkaloids).(for cinchona and cocoa alkaloids).
Separation and final purification may beSeparation and final purification may be
done using fractional precipitation ordone using fractional precipitation or
fractional crystallization of salts.fractional crystallization of salts.
Chromatograpy is used for complexChromatograpy is used for complex
alkaloids and if only small amounts ofalkaloids and if only small amounts of
alkaloids are needed.alkaloids are needed.
Volatile liquid alkaloids (nicotine) areVolatile liquid alkaloids (nicotine) are
isolated by distillation – alkaloid isisolated by distillation – alkaloid is
distilled off in steam. Nicotine is andistilled off in steam. Nicotine is an
important insecticide, and largeimportant insecticide, and large
amounts are prepared from the partsamounts are prepared from the parts
of the tobacco plant which is not usedof the tobacco plant which is not used
for tobacco manufacturefor tobacco manufacture

Pharmacological Action & UsesPharmacological Action & Uses
CNS Action: stimulants (caffeine)CNS Action: stimulants (caffeine)
or depressants (morphine)or depressants (morphine)
ANS: sympathomimeticsANS: sympathomimetics
(ephedrine) or sympatholytics(ephedrine) or sympatholytics
(yohimbine, ergot alkaloids),(yohimbine, ergot alkaloids),
parasympathomimeticsparasympathomimetics
(pilocarpine), anticholinergics(pilocarpine), anticholinergics
(choline), ganglioplegics(choline), ganglioplegics
(nicotine).(nicotine).
Also: local anesthetics (cocaine),Also: local anesthetics (cocaine),
defibrillation (quinidine), anti-defibrillation (quinidine), anti-
tumour agents (ellipticine),tumour agents (ellipticine),
anti-malarial (quinine), anti-anti-malarial (quinine), anti-
bacterials (berberine), andbacterials (berberine), and
amoebicides (emetine).amoebicides (emetine).

These actions lead toThese actions lead to
the extensive use ofthe extensive use of
alkaloid containingalkaloid containing
herbs and drugs.herbs and drugs.
Although some areAlthough some are
used as galenicalsused as galenicals
(belladonna, datura,(belladonna, datura,
and henbane), mostand henbane), most
are used as startingare used as starting
materials for industrialmaterials for industrial
extraction (morphineextraction (morphine
from poppy straw orfrom poppy straw or
opium, and quinineopium, and quinine
fromfrom CinchonaCinchona bark.bark.

Chances Of Having Twins Can BeChances Of Having Twins Can Be
Modified By DietModified By Diet An obstetrician well known for his care of and research intoAn obstetrician well known for his care of and research into
multiple-birth pregnancies has found that dietary changesmultiple-birth pregnancies has found that dietary changes
can affect a woman's chances of having twins, and that hercan affect a woman's chances of having twins, and that her
overall chance is determined by a combination of diet andoverall chance is determined by a combination of diet and
heredity. By comparing the twinning rate of vegan women,heredity. By comparing the twinning rate of vegan women,
who consume no animal products, with that of women whowho consume no animal products, with that of women who
do eat animal products, Gary Steinman, MD, PhD, ando eat animal products, Gary Steinman, MD, PhD, an
attending doctor at Long Island Jewish (LIJ) Medicalattending doctor at Long Island Jewish (LIJ) Medical
Center in New Hyde Park, NY, found that the women whoCenter in New Hyde Park, NY, found that the women who
consume animal products, specifically dairy, are five timesconsume animal products, specifically dairy, are five times
more likely to have twins. The study is reported in the Maymore likely to have twins. The study is reported in the May
2006 issue of the Journal of Reproductive Medicine,2006 issue of the Journal of Reproductive Medicine,
available May 20.available May 20.
The culprit may be insulin-like growth factor (IGF), a proteinThe culprit may be insulin-like growth factor (IGF), a protein
that is released from the liver of animals -- includingthat is released from the liver of animals -- including
humans -- in response to growth hormone, circulates in thehumans -- in response to growth hormone, circulates in the
blood and makes its way into the animal's milk. IGFblood and makes its way into the animal's milk. IGF
increases the sensitivity of the ovaries to follicle stimulatingincreases the sensitivity of the ovaries to follicle stimulating
hormone, thereby increasing ovulation. Some studies alsohormone, thereby increasing ovulation. Some studies also
suggest that IGF may help embryos survive in the earlysuggest that IGF may help embryos survive in the early
stages of development. The concentration of IGF in thestages of development. The concentration of IGF in the
blood is about 13 percent lower in vegan women than inblood is about 13 percent lower in vegan women than in
women who consume dairy.women who consume dairy.

Biogenesis of AlkaloidsBiogenesis of Alkaloids
Alkaloids are produced in plants by basicAlkaloids are produced in plants by basic
substances and reactions well-known insubstances and reactions well-known in
organic chemistry.organic chemistry.
Biosynthetic origin cannot be discussed inBiosynthetic origin cannot be discussed in
general terms for all alkaloids, instead itgeneral terms for all alkaloids, instead it
has to be covered separately for each ofhas to be covered separately for each of
the major groups of alkaloidsthe major groups of alkaloids

True alkaloids are based on an amino acid (pre-True alkaloids are based on an amino acid (pre-
cursor).cursor).
Only a few amino acids form the pre-cursors for allOnly a few amino acids form the pre-cursors for all
alkaloids: ornithine, lysine, phylalanine, tyrosine,alkaloids: ornithine, lysine, phylalanine, tyrosine,
tryptophan, histidine and anthranilic acid.tryptophan, histidine and anthranilic acid.
Alkaloid formation may require the involvement ofAlkaloid formation may require the involvement of
only one molecule of amino acid, or 2 moleculesonly one molecule of amino acid, or 2 molecules
of the same AA, or less commonly, 2 moleculesof the same AA, or less commonly, 2 molecules
of different AA or else several molecules of theof different AA or else several molecules of the
same AA.same AA.
The formation starts with the formation of a SchiffThe formation starts with the formation of a Schiff
base or a Mannich reaction.base or a Mannich reaction.
When the alkaloid has additional C-atoms, theseWhen the alkaloid has additional C-atoms, these
play important roles in other metabolicplay important roles in other metabolic
pathways.pathways.

Main Pre-cursors for AlkaloidsMain Pre-cursors for Alkaloids
a.a. Group 1: Aliphatic AA’s – ornithine & lysineGroup 1: Aliphatic AA’s – ornithine & lysine
* Pre-cursors to pyrrolidien, piperridine &* Pre-cursors to pyrrolidien, piperridine &
tropane alkaloidstropane alkaloids
a.a. Aromatic AA – Phenylalanine, tyrosine,Aromatic AA – Phenylalanine, tyrosine,
tryptophanetryptophane
c. Precursors of terpenes, steroids & polyketides –c. Precursors of terpenes, steroids & polyketides –
often together with the aliphatic or aromaticoften together with the aliphatic or aromatic
AA’sAA’s  result in alkaloids of mixedresult in alkaloids of mixed
biosynthetic originbiosynthetic origin

Hetrocyclic AlkaloidsHetrocyclic Alkaloids
Pyrrolidine AlkaloidsPyrrolidine Alkaloids
Piperridine/pyridinePiperridine/pyridine
PyrrolizidinePyrrolizidine
Tropane AlkaloidsTropane Alkaloids
Quinoline AlkaloidsQuinoline Alkaloids
Isoquinoline AlkaloidsIsoquinoline Alkaloids
Opium AlkaloidsOpium Alkaloids
AporphineAporphine
NorlupinaneNorlupinane
Ipecac AlkaloidsIpecac Alkaloids
Indole AlkaloidsIndole Alkaloids
IndolizidineIndolizidine
ImidazoleImidazole
Purine AlkaloidsPurine Alkaloids
ProtoalkaloidsProtoalkaloids
SteroidalSteroidal
TerpenoidTerpenoid

Classification of Alkaloids
On the basis of various ring structure alkaloids are broadly divided
into the following major groups:
Alkaloids are classified into the following groups:
1. Pyridine-piperidine alkaloids
2. Tropane alkaloids
3. Quinoline alkaloids
4. Isoquinoline alkaloids
5. Imidazole alkaloids
6. Steroidal alkaloids
7. Alkaloidal amines

1. Pyridine-piperidine Alkaloids
 Possess pyrrolidine, pyridine, piperidine ring structure or a combination
of these rings as their basic nuclei
 Used as anthelmintics, respiratory stimulants and as insecticides
 Example: Lobelia, Ricinus, Tobacco
Pyridine Piperidine Pyrrolidine

2. Tropane Alkaloids
Possess a dicyclic compound, tropane, as their basic nuclei which is
formed by the condensation of piperidine and N-methyl pyrrolidine ring
Used as spasmolytic and anticholinergic and mydriatic agents
Example: Atropine, Hyoscine, Hyoscyamine, tigloidine, cocaine
Tropane
PiperidinePyrrolidine
N-CH3
+
=

3. Quinoline Alkaloids
 Possess quinoline as their basic nuclei
 Used in the treatment of malaria
 Example: quinine, quinidine, cinchoninde, cinchonidine
N
Quinoline Quinoline

4. Isoquinoline Alkaloids
N
Quinoline
N
Isoquinoline
 Possess isoquinoline as their basic nuclei
 Used as anti-amoebic, skeletal muscle relaxants, analgesics,
hypnotics and astringents
 Example:

Alkaloids in Ipecac( emetine, cephaeline, psychotrine)

Alkaloids of opium( morphine, codeine, thebaine)

5. Indole Alkaloids
Indole
 Possess indole ring as their basic nuclei
 Used in the treatment of high blood pressure, Hodgkin’s disease,
leukaemia and as oxotocics
 Example:

Rauwolfia and its alkaloids( reserpine, deserpidine, rescinnamine)

Ergot and its alkaloids( ergotamine, ergometrine)

6. Imidazole alkaloids
Imidazole
 Possess imidazole ring as their basic nuclei
 Used as cholinergic drug
 Example: Pilocarpine

7. Steroidal Alkaloids
 Possess a cyclopentenoperhydrophenanthrene nucleus
 Used as hypotensives, cardiac depressants, sedatives and anti-
dysenteric agents
 Example: protoveratrine, veretramin, veratridin and germidine

8. Alkaloidal Amines
_
H-C-OH
H-C-NH-CH3
CH3
ephedrine
 Possess nitrogen atoms in side chains and called non-heterocyclic
alkaloids
 Used as bronchodilator, vasoconstrictor and cardiac stimulant and
as a uppressant for gout
 Example: ephedrine, colchicine
ephedrine

Derived from tropine and consist of mandelic,Derived from tropine and consist of mandelic,
tropic or benzoic acid esters of tropine.tropic or benzoic acid esters of tropine.
Are very closely related to each otherAre very closely related to each other
All have pronounced physiological actions.All have pronounced physiological actions.
Natural alkaloids includeNatural alkaloids include
HyoscyamineHyoscyamine
HyoscineHyoscine
AtropineAtropine
CocaineCocaine
The above mentioned alkaloids occur within theThe above mentioned alkaloids occur within the
Solanaceae family (except cocaine – fromSolanaceae family (except cocaine – from
Erythroxylaceae family)Erythroxylaceae family)

Atropine & HyoscineAtropine & Hyoscine
Have the same structure – differ only in theirHave the same structure – differ only in their
optical activity.optical activity.
Also have different physiological actionsAlso have different physiological actions
Atropine – deadly nightshade,Atropine – deadly nightshade, Atropa belladonnaAtropa belladonna::
dilates eye pupils, decreases sweating,dilates eye pupils, decreases sweating,
produces stomach acid and saliva & relaxesproduces stomach acid and saliva & relaxes
smooth muscle (asthma and colic).smooth muscle (asthma and colic).
Hyoscine – black henbane,Hyoscine – black henbane, Hyoscyamus nigerHyoscyamus niger::
Limited influence on the CNS. SedativeLimited influence on the CNS. Sedative
Cocaine: Narcotic properties & local anaestheticCocaine: Narcotic properties & local anaesthetic
action (e.g. used in eye drops).action (e.g. used in eye drops).

Datura stramonium -Datura stramonium - SolanaceaeSolanaceae
Definition: Stramonium LeafDefinition: Stramonium Leaf
consists of the driedconsists of the dried
leaves or dried leavesleaves or dried leaves
and flowering tops ofand flowering tops of
Datura stramoniumDatura stramonium. The. The
drug should contain atdrug should contain at
least 0.25% alkaloidsleast 0.25% alkaloids
calculated ascalculated as
hyoscyamine.hyoscyamine.
Common names:Common names:
Stramonium leaf,Stramonium leaf,
Thornapple, Jimson orThornapple, Jimson or
Jamestown weedJamestown weed

Datura stramoniumDatura stramonium - Constituents- Constituents
Main (Tropane) AlkaloidsMain (Tropane) Alkaloids
* Hyoscyamine* Hyoscyamine
• Hyoscine (2:1)Hyoscine (2:1)
Younger plants: hyoscine –Younger plants: hyoscine –
predominant alkaloidpredominant alkaloid
Also containsAlso contains
• AtropineAtropine
• Larger stems contain littleLarger stems contain little
alkaloid, and drug shouldalkaloid, and drug should
contain no more than 3% ofcontain no more than 3% of
stems with a diameterstems with a diameter
>5mm>5mm

Datura stramoniumDatura stramonium – Allied Drugs– Allied Drugs
& Adulterants& Adulterants
ALLIED DRUGSALLIED DRUGS
Datura innoxiaDatura innoxia
Datura metelDatura metel (dried(dried
leaves are also curledleaves are also curled
and twisted – like D.and twisted – like D.
stramonium), but arestramonium), but are
browner in colour.browner in colour.
Datura sanguineaDatura sanguinea
ADULTERANTSADULTERANTS
Xanthium, CarthamusXanthium, Carthamus
andand ChenopodiumChenopodium
leavesleaves
(easily distinguished(easily distinguished
from original herb)from original herb)

Uses ofUses of Datura stramoniumDatura stramonium
Atropine: Stimulant on CNSAtropine: Stimulant on CNS
Depresses nerve endingsDepresses nerve endings
on the secretory glandson the secretory glands
and smooth muscleand smooth muscle
Hyoscine: lacks CNSHyoscine: lacks CNS
stimulant action ofstimulant action of
atropineatropine
Sedative – motion sicknessSedative – motion sickness
Atropine & Hyoscine: usedAtropine & Hyoscine: used
in opthalmic practice toin opthalmic practice to
dilate the pupil of the eye.dilate the pupil of the eye.

Hyoscyamus niger -Hyoscyamus niger - SolanaceaeSolanaceae
Definition: HyoscyamusDefinition: Hyoscyamus
leaf consists of theleaf consists of the
dried leaves or drieddried leaves or dried
leaves and floweringleaves and flowering
tops oftops of HyoscyamusHyoscyamus
nigerniger. It should. It should
contain at least 0.05%contain at least 0.05%
alkaloids –alkaloids –
hyoscyamine.hyoscyamine.
Common names:Common names:
HenbaneHenbane

Hyoscyamus nigerHyoscyamus niger - Constituents- Constituents
MainlyMainly
• HyoscyamineHyoscyamine
• Hyoscine (mainHyoscine (main
constituent)constituent)

Hyoscyamus niger –Hyoscyamus niger – Allied DrugsAllied Drugs
• Hyoscyamus albus
(petiolate stem-leaves
and pale yellow, non-
veined petals – bottom
left).
• Hyosycamus muticus (top
right)
• Hyoscyamus pusillus
• Hyoscyamus aureus
• Hyoscyamus reticulatus
(Indian henbane – bottom
right)

Hyoscyamus nigerHyoscyamus niger - Uses- Uses
Resembles belladonnaResembles belladonna
and stramonium inand stramonium in
action – only weaker.action – only weaker.
Higher hyoscine contentHigher hyoscine content
– less likely to cause– less likely to cause
cerebral stimulation .cerebral stimulation .
Used to relieve spasmUsed to relieve spasm
of the urinary tractof the urinary tract

Atropa belladonnaAtropa belladonna - Solanaceae- Solanaceae
Definition: Belladonna herbDefinition: Belladonna herb
leaves and flowering topsleaves and flowering tops
ofof Atropa belladonnaAtropa belladonna,,
containing at least 0.3%containing at least 0.3%
alkaloids (hyoscyamine).alkaloids (hyoscyamine).
Should not contain >3%Should not contain >3%
stem >5mm in diameter.stem >5mm in diameter.
USP also allowsUSP also allows A.A.
acuminataacuminata in thein the
Belladonna LeafBelladonna Leaf
monograph.monograph.

Atropa belladonnaAtropa belladonna - Constituents- Constituents
Main (Tropane) alkaloidMain (Tropane) alkaloid
• HyoscyamineHyoscyamine
• ScopoletinScopoletin
• Calcium oxalateCalcium oxalate

Atropa belladonnaAtropa belladonna
ALLIED DRUGSALLIED DRUGS
Indian belladonna
(Atropa acuminata) –
yellow-brown flowers
& brown-green
leaves.
Atropa baetica (yellow
flowers and black
berries) – endangered
species
ADULTERANTSADULTERANTS
Phytolacca decandra
Ailanthus glandulosa

Atropa belladonnaAtropa belladonna - Uses- Uses
Used as a sedativeUsed as a sedative
To stop bodilyTo stop bodily
secretions (e.g.secretions (e.g.
saliva)saliva)
Root preparations areRoot preparations are
used externallyused externally

Pyridine AlkaloidsPyridine Alkaloids
Also referred to asAlso referred to as
Pyrrolizidine alkaloidsPyrrolizidine alkaloids
IncludeInclude
Lobeline (Lobelia herb)Lobeline (Lobelia herb)
– respiratory stimulant– respiratory stimulant
 Used in asthmaUsed in asthma
preparations.preparations.
NicotineNicotine (Nicotiana(Nicotiana
tabacumtabacum and otherand other
Nicotina sppNicotina spp) – toxic) – toxic
 used as anused as an
insecticideinsecticide
LobelineLobeline

Lobelia inflata-Lobelia inflata- CapmanulaceaeCapmanulaceae
Definition: Lobelia herbDefinition: Lobelia herb
aerial parts ofaerial parts of LobeliaLobelia
inflata.inflata.
Common Names: Lobelia,Common Names: Lobelia,
Indian Tobacco)Indian Tobacco)
History: Traditionally usedHistory: Traditionally used
by the Native Americansby the Native Americans
for asthma.for asthma.

Lobelia inflataLobelia inflata – Constituents– Constituents
Contains PyrrolizidineContains Pyrrolizidine
AlkaloidsAlkaloids
Most importantMost important
• LobelineLobeline
AlsoAlso
LobelidineLobelidine
LobelanineLobelanine
IsolobelanineIsolobelanine

Lobelia inflataLobelia inflata - Uses- Uses
AsthmaAsthma
Chronic bronchitisChronic bronchitis
Anti-smoking preparationsAnti-smoking preparations
Injection of lobelineInjection of lobeline
hydrochloride is used inhydrochloride is used in
the resuscitation ofthe resuscitation of
newborn infants.newborn infants.
Caution: Toxic doses theCaution: Toxic doses the
herb has a paralyticherb has a paralytic
effect.effect.

Consist of alkaloids andConsist of alkaloids and
alkaloid salts obtainedalkaloid salts obtained
from the bark of certainfrom the bark of certain
Cinchona speciesCinchona species
(Quinine, Quinidine,(Quinine, Quinidine,
Cinchonine,Cinchonine,
Cinchonidine). TheCinchonidine). The
amount of alkaloidsamount of alkaloids
present depend on thepresent depend on the
species, environment ofspecies, environment of
the tree, age, and methodthe tree, age, and method
of bark collection.of bark collection.
Quinine: Anti-malarialQuinine: Anti-malarial
Synthetic alkaloids are nowSynthetic alkaloids are now
used as substitutes forused as substitutes for
quinine for malaria.quinine for malaria.

CinchonaCinchona Bark - RubiaceaeBark - Rubiaceae
Definition: Cinchona barkDefinition: Cinchona bark
consists of the variousconsists of the various
species races andspecies races and
hybrids ofhybrids of CinchonaCinchona,,
large trees indigenous tolarge trees indigenous to
Colombia Equador, PeruColombia Equador, Peru
& Bolivia& Bolivia
INCLUDESINCLUDES
C. Succirubra, C. calisaya,C. Succirubra, C. calisaya,
C. ledgeriana, C.C. ledgeriana, C.
officinalisofficinalis

CinchonaCinchona - History- History
Historically played anHistorically played an
important role in theimportant role in the
treatment of malaria.treatment of malaria.
This has now lessenedThis has now lessened
with the introduction ofwith the introduction of
synthetic drugs.synthetic drugs.
Traditionally not used by theTraditionally not used by the
native South Americannative South American
Indians (bitter tasteIndians (bitter taste
inspired them with fear).inspired them with fear).
First used as a medicineFirst used as a medicine
in Peru in 1630 – used toin Peru in 1630 – used to
cure fevers.cure fevers.

CinchonaCinchona - Constituents- Constituents
MainlyMainly
• QuinineQuinine
• QuinidineQuinidine
AlsoAlso
• QuinicineQuinicine
• CinchonicineCinchonicine
• Cinchotannic acidCinchotannic acid
• AnthraquinonesAnthraquinones
• Leaves contain IndoleLeaves contain Indole
AlkaloidsAlkaloids

CinchonaCinchona – Chemical Tests– Chemical Tests
Colour reaction for quinine and quinidine alkaloidsColour reaction for quinine and quinidine alkaloids
Use bromine and ammonia (the thalleioquin test)Use bromine and ammonia (the thalleioquin test)
Powdered cinchona is slightly moistened withPowdered cinchona is slightly moistened with
glacial acetic acid & heated in an ignition tubeglacial acetic acid & heated in an ignition tube
Red drops condense on the sides of the tube.Red drops condense on the sides of the tube.
Cinchona bark therefore gives reactions forCinchona bark therefore gives reactions for
phlobatannins.phlobatannins.

CinchonaCinchona – Allied Drugs– Allied Drugs
Barks of certain speciesBarks of certain species
ofof RemijiaRemijia
e.g.e.g. R. pedunculataR. pedunculata
R. purdienaR. purdiena

Cinchona Bark - UsesCinchona Bark - Uses
Bitter tonicsBitter tonics
StomachicsStomachics
Used as garglesUsed as gargles
(tannins in bark –(tannins in bark –
astringent)astringent)
MalariaMalaria
Prophylaxis of cardiacProphylaxis of cardiac
arrhythmiasarrhythmias
Treatment of atrialTreatment of atrial
fibrillationfibrillation

Isoquinoline AlkaloidsIsoquinoline Alkaloids
Drugs: Opium and Ipecac.Drugs: Opium and Ipecac.
Alkaloids of both theseAlkaloids of both these
herbs are in the sameherbs are in the same
group, yet they differgroup, yet they differ
chemically and also inchemically and also in
their pharmaceuticaltheir pharmaceutical
actions.actions.
Opium Alkaloids: morphine,Opium Alkaloids: morphine,
codeine, ethylmorphine,codeine, ethylmorphine,
thebaine, heroine,thebaine, heroine,
papaverine.papaverine.
Ipecac Alkaloids: emetine,Ipecac Alkaloids: emetine,
cephaeline, psychotrine,cephaeline, psychotrine,
methylpsychotrinemethylpsychotrine
EmetineEmetine

Opium Alkaloids – OpiumOpium Alkaloids – Opium
Definition: Opium (Raw Opium) isDefinition: Opium (Raw Opium) is
the latex obtained by incisionthe latex obtained by incision
from the unripe capsules offrom the unripe capsules of
PapaverPapaver somniferumsomniferum, from the, from the
Papaveraceae Family. It isPapaveraceae Family. It is
dried partially by spontaneousdried partially by spontaneous
evaporation and partly byevaporation and partly by
artificial heat.artificial heat.
Commercially known as IndianCommercially known as Indian
opium.opium.
BP monograph: opium isBP monograph: opium is
intended only as a startingintended only as a starting
point for the manufacture ofpoint for the manufacture of
galenicals, and should not begalenicals, and should not be
dispensed as such.dispensed as such.

Papaver somniferumPapaver somniferum - Constituents- Constituents
30 Alkaloids30 Alkaloids
6 main ones6 main ones
• MorphineMorphine
• CodeineCodeine
• ThebaineThebaine
• NoscapineNoscapine
• NarceineNarceine
• papaverinepapaverine

Tests for Opium AlkaloidsTests for Opium Alkaloids
Morphine: soluble inMorphine: soluble in
sodium hydroxidesodium hydroxide
(due to phenols)(due to phenols)
Codeine is precipitatedCodeine is precipitated
by sodium hydroxide.by sodium hydroxide.
Other chemical testsOther chemical tests
are found inare found in
pharmacopoeias.pharmacopoeias.

Opium - AdulterantsOpium - Adulterants
Adulterated with sugaryAdulterated with sugary
fruits, gums, powderedfruits, gums, powdered
poppy capsules and otherpoppy capsules and other
substances.substances.
Adulteration is now uselessAdulteration is now useless
(product is first analysed(product is first analysed
and the price is paidand the price is paid
depending on the contentdepending on the content
of morphine and otherof morphine and other
alkaloids)alkaloids)

Papaver somniferumPapaver somniferum UsesUses
Opium & Morphine:Opium & Morphine:
Relieve painRelieve pain
Hypnotics (affect the sensoryHypnotics (affect the sensory
nerve cells of the cerebrum).nerve cells of the cerebrum).
Opium (closely resemblesOpium (closely resembles
morphine) – exerts actionmorphine) – exerts action
more slowly – preferable tomore slowly – preferable to
morphine (e.g in diarrhoea).morphine (e.g in diarrhoea).
Opium: also a diaphoreticOpium: also a diaphoretic
CodeineCodeine
Milder sedativeMilder sedative
Relieve coughRelieve cough
Habitual use may causeHabitual use may cause
constipationconstipation
Both Morphine & CodeineBoth Morphine & Codeine
decrease metabolismdecrease metabolism
Codeine – was used to treatCodeine – was used to treat
diabetes (before thediabetes (before the
introduction of insulin).introduction of insulin).

Codeine May Be No Cure ForCodeine May Be No Cure For
CoughCough
Researchers at the University of Manchester‘Researchers at the University of Manchester‘
North West Lung Centre have found thatNorth West Lung Centre have found that
codeinecodeine
- a standard ingredient in cough remedies –a standard ingredient in cough remedies –
could be no more effective than an inactivecould be no more effective than an inactive
placebo compound at treating cough.placebo compound at treating cough.
Scientists at the Centre, which is based atScientists at the Centre, which is based at
Wythenshawe Hospital, studied a sample ofWythenshawe Hospital, studied a sample of
patients with chronic lung disease. Afterpatients with chronic lung disease. After
coughing was induced with citric acid they werecoughing was induced with citric acid they were
given either codeine or a placebo, and sentgiven either codeine or a placebo, and sent
home wearing a lapel microphone to record theirhome wearing a lapel microphone to record their
coughing during the day and night.coughing during the day and night.
Lead researcher Dr. Jacyln Smith said:Lead researcher Dr. Jacyln Smith said:
"Codeine"Codeine
has long been considered the standard antihas long been considered the standard anti
cough agent against which others arecough agent against which others are
measured,measured,
but until now little has been known about itsbut until now little has been known about its
After the placebo therapy the patients' coughingAfter the placebo therapy the patients' coughing
fell from an average of 8.27 seconds per hour tofell from an average of 8.27 seconds per hour to
7.22 seconds, and after codeine to 6.417.22 seconds, and after codeine to 6.41
seconds.seconds.
"Even though there was a significant reduction"Even though there was a significant reduction
after codeine, from a statistical standpoint thereafter codeine, from a statistical standpoint there
was really no difference between codeine andwas really no difference between codeine and
placebo - despite the fact that the dose ofplacebo - despite the fact that the dose of
codeine used far exceeds that in over-thecodeine used far exceeds that in over-the
counter cough remedies.“counter cough remedies.“
The findings were reported in Journal of AllergyThe findings were reported in Journal of Allergy
and Clinical Immunology, and seem to confirmand Clinical Immunology, and seem to confirm
some medics' view that reductions in coughingsome medics' view that reductions in coughing
after codeine are attributable to a placeboafter codeine are attributable to a placebo
effecteffect

Ipecac Alkaloids - IpecacuanhaIpecac Alkaloids - Ipecacuanha
Definition: IpecacuanhaDefinition: Ipecacuanha
(Ipecacuanha Root) is(Ipecacuanha Root) is
the dried root orthe dried root or
rhizome and root ofrhizome and root of
CephaelisCephaelis
ipecacuanhaipecacuanha of theof the
Rubiaceae family.Rubiaceae family.
It should contain at leastIt should contain at least
2% alkaloids2% alkaloids

Ipecacuanha CollectionIpecacuanha Collection
A pointed stick is usedA pointed stick is used
to lever the plant upto lever the plant up
from the ground.from the ground.
Most of the roots areMost of the roots are
then removed.then removed.
The plant is replacedThe plant is replaced
into the ground,into the ground,
where it will continue twhere it will continue t
produce more crops.produce more crops.
Roots are dried in theRoots are dried in the
sun or by fire andsun or by fire and
then transported.then transported.

Ipecacuanha ConstituentsIpecacuanha Constituents
Ipecac alkaloidsIpecac alkaloids
(isoquinoline) alkaloids(isoquinoline) alkaloids
MainlyMainly
• EmetineEmetine
• PsychotrinePsychotrine
• CephaelineCephaeline
AlsoAlso
• EmetamineEmetamine
• Psychotrine methyletherPsychotrine methylether
• Ipecoside (glycoside)Ipecoside (glycoside)

Ipecacuanha - AdulterantsIpecacuanha - Adulterants
Other “ipecacuanhas”,Other “ipecacuanhas”,
different roots said todifferent roots said to
have emetichave emetic
properties.properties.
These are easilyThese are easily
distinguished from thedistinguished from the
original root and areoriginal root and are
now very rarelynow very rarely
imported.imported.

Test for emetineTest for emetine
Mix 0.5g powdered herbMix 0.5g powdered herb
with 20ml HCL and 5mlwith 20ml HCL and 5ml
water.water.
FilterFilter
To 2ml filtrate add 0.01gTo 2ml filtrate add 0.01g
potassium chloratepotassium chlorate
Result: if emetine isResult: if emetine is
present, a yellow colourpresent, a yellow colour
appears. After standingappears. After standing
for 1hr, changes to red.for 1hr, changes to red.

Ipecacuanha UsesIpecacuanha Uses
ExpectorantExpectorant
EmeticEmetic
Amoebic DysentryAmoebic Dysentry
Emetine is moreEmetine is more
expectorant and lessexpectorant and less
emetic in action thanemetic in action than
cephaelinecephaeline
Psychotrine: selective HIVPsychotrine: selective HIV
inhibotors (study couldinhibotors (study could
lead to therapeuticallylead to therapeutically
useful agents)useful agents)

Indole AlkaloidsIndole Alkaloids
These are found in Ergot &These are found in Ergot &
Nux VormicaNux Vormica
Ergot alkloids: based onErgot alkloids: based on
lysergic acid (LSD –lysergic acid (LSD –
lysergic acidlysergic acid
diethylamide)diethylamide)
Nux Vormica: 2 importantNux Vormica: 2 important
alkaloids: strychininealkaloids: strychinine
and brucine.and brucine.
Strychinine: CNSStrychinine: CNS
stimulant, lethal in largestimulant, lethal in large
doses (uses as a poison)doses (uses as a poison)

Other plants containing indole alkaloidsOther plants containing indole alkaloids
Rauwolfia serpentinaRauwolfia serpentina (Indian snakeroot) –(Indian snakeroot) –
HypertensionHypertension
Gelsemium sempervirensGelsemium sempervirens – contains gelsemine,– contains gelsemine,
sempervine.sempervine.
Used as a CNS depressant – used forUsed as a CNS depressant – used for
migraines.migraines.
Catharanthus roseusCatharanthus roseus – vinblastine, vincristine.– vinblastine, vincristine.
Used for migraineUsed for migraine

Ergot (Ergot of Rye)Ergot (Ergot of Rye)
Defintion: Ergot (ErgotDefintion: Ergot (Ergot
of Rye) is the driedof Rye) is the dried
sclerotium of asclerotium of a
fungus,fungus, ClavicepsClaviceps
purpurea,purpurea, arising inarising in
the ovary of the rye,the ovary of the rye,
Secale cerealeSecale cereale..
Controlled fieldControlled field
cultivation on rye iscultivation on rye is
the main source ofthe main source of
crude drug.crude drug.

Ergot - HistoryErgot - History
World-wide, sporadicWorld-wide, sporadic
reports of ergotreports of ergot
poisoning (ergotism)poisoning (ergotism)
still appear instill appear in
literature: 1992 anliterature: 1992 an
analysis of rye flouranalysis of rye flour
sold in Canadasold in Canada
showed low levels ofshowed low levels of
fungus contamination.fungus contamination.
Of 128 samples, 118Of 128 samples, 118
were contained thewere contained the
fungus.fungus.

Ergot - ConstituentsErgot - Constituents
Ergot alkaloidsErgot alkaloids
(ergolines)(ergolines)
IncludeInclude
• Ergonovine (water-Ergonovine (water-
soluble) Alkaloidssoluble) Alkaloids
• Ergotoxine &Ergotoxine &
Ergotamine alkaloidsErgotamine alkaloids
(water-insoluble)(water-insoluble)

Ergot Substitutes & StorageErgot Substitutes & Storage
SUBSTITUTESSUBSTITUTES
• Ergot of WheatErgot of Wheat
• Ergot of OatsErgot of Oats
• Ergot of Diss (reed)Ergot of Diss (reed)
STORAGESTORAGE
Liable to attacks by insects,Liable to attacks by insects,
moulds & bacteria.moulds & bacteria.
Dried after collection &Dried after collection &
stored in a cool, drystored in a cool, dry
place. If powdered andplace. If powdered and
not immediately defattednot immediately defatted
– looses lots of its– looses lots of its
activity. If defatted – canactivity. If defatted – can
keep for an extendedkeep for an extended
period.period.

Traditionally used inTraditionally used in
labour to assist thelabour to assist the
deliverydelivery
Reduce post-partumReduce post-partum
haemorrhagehaemorrhage
Ergometrine producesErgometrine produces
oxyticic effects.oxyticic effects.
Ergot - UsesErgot - Uses

Nux Vormica - LoganiaceaeNux Vormica - Loganiaceae
Definition: Nux vormicaDefinition: Nux vormica
consists of the dried, ripeconsists of the dried, ripe
seeds ofseeds of Strychnos nux-Strychnos nux-
vormicavormica, (a tree growing, (a tree growing
up 13m in India, Thailand,up 13m in India, Thailand,
South Vietnam andSouth Vietnam and
Cambodia).Cambodia).
History: in 16History: in 16thth
Century itCentury it
was sold in Europe,was sold in Europe,
mainly used for poisoningmainly used for poisoning
animals.animals.

Nux Vormica – Collection &Nux Vormica – Collection &
PreparationPreparation
Fruit consists a berryFruit consists a berry
about the size of aabout the size of a
small orange.small orange.
When ripe it has a hardWhen ripe it has a hard
orange-yelloworange-yellow
pericarp and a white,pericarp and a white,
pulpy interior –pulpy interior –
containing 1-5 seeds.containing 1-5 seeds.
Seeds are washed toSeeds are washed to
remove pulp andremove pulp and
dried. Exported indried. Exported in
small sacks known assmall sacks known as
pockets.pockets.

Nux Vormica - ConstituentsNux Vormica - Constituents
2-5% Indole alkaloids2-5% Indole alkaloids
MainlyMainly
• StrychineStrychine
• BrucineBrucine
Strychine is moreStrychine is more
physiological activephysiological active
than brucinethan brucine

Nux Vormica - UsesNux Vormica - Uses
Action of the whole drugAction of the whole drug
resembles the action ofresembles the action of
StrychnineStrychnine
Formerly used as aFormerly used as a
circulatory stimulantcirculatory stimulant
(e.g. in surgical shock)(e.g. in surgical shock)
Now used mainly as aNow used mainly as a
respiratory stimulant (inrespiratory stimulant (in
certain cases ofcertain cases of
poisoning)poisoning)
Bitter - used to improveBitter - used to improve
appetite & digestionappetite & digestion
Commonly misused as aCommonly misused as a
‘General Tonic’‘General Tonic’

Nux Vormica – Allied DrugsNux Vormica – Allied Drugs
Ignatius beans (seedsIgnatius beans (seeds
ofof Strychnos ignatiiStrychnos ignatii) –) –
fruits are larger thanfruits are larger than
those of Nux vormicathose of Nux vormica
& may contain up t 30& may contain up t 30
seeds. Also darkseeds. Also dark
grey in colour.grey in colour.
AlsoAlso S. potatorumS. potatorum andand
S. nux-blandaS. nux-blanda ––
contai no strychninecontai no strychnine
or brucineor brucine

Rauwolfia serpentineRauwolfia serpentine --
ApocynaceaeApocynaceae
Defintion: RauwolfiaDefintion: Rauwolfia
rhizome and roots ofrhizome and roots of
Rauwolfia serpentiana.Rauwolfia serpentiana.
(a small shrub found in(a small shrub found in
India, Pakistan, Java andIndia, Pakistan, Java and
Thailand).Thailand).
Common name: Rauwolfia,Common name: Rauwolfia,
Indian SnakerootIndian Snakeroot

Rauwolfia - ConstituentsRauwolfia - Constituents
30 Alkaloids30 Alkaloids
Main alkaloidMain alkaloid
• ReserpineReserpine
AlsoAlso
• RauwolfineRauwolfine
• SerpentineSerpentine
• SerpentinineSerpentinine
New alkaloids continue toNew alkaloids continue to
be isolated.be isolated.

Rauwolfia - UsesRauwolfia - Uses
Essential HypertensionEssential Hypertension
Malignant HypertensionMalignant Hypertension
NeuropsychiatricNeuropsychiatric
DisordersDisorders
Cardiac arrhythmiasCardiac arrhythmias
Circulatory DiseaseCirculatory Disease

Rauwolfia – CAUTIONS!Rauwolfia – CAUTIONS!
Conflicting reports on theConflicting reports on the
possible involvement ofpossible involvement of
rauwolfia alkaloids inrauwolfia alkaloids in
breast cancer.breast cancer.
Suggested that the alkaloidsSuggested that the alkaloids
do not initiate thedo not initiate the
carcinogenic process, butcarcinogenic process, but
promote breast cancerpromote breast cancer
from previously initiatedfrom previously initiated
cells.cells.
DEPRESSIONDEPRESSION

ProtoalkaloidsProtoalkaloids
Alkaloid-like amines.Alkaloid-like amines.
Have no nitrogen asHave no nitrogen as
part of the hetrocyclicpart of the hetrocyclic
ring.ring.
Examples: ephedrineExamples: ephedrine
and adrenalineand adrenaline
Both cause dilation ofBoth cause dilation of
the bronchi (asthma),the bronchi (asthma),
increase heart rateincrease heart rate
and peripheraland peripheral
vasoconstriction.vasoconstriction.

Ephedra - EphedraceaeEphedra - Ephedraceae
Definition: Various speciesDefinition: Various species
of Ephedra are used as aof Ephedra are used as a
source of the alkaloidssource of the alkaloids
Ephedrine andEphedrine and
Psuedoephidrine.Psuedoephidrine.
These includeThese include E. major, E.E. major, E.
intermedia, E. sinica andintermedia, E. sinica and
E. equisetina.E. equisetina.
Common name: Ephedra,Common name: Ephedra,
(Ma-huang)(Ma-huang)

Ephedra - ConstituentsEphedra - Constituents
AlkaloidsAlkaloids
(protoalkaloids)(protoalkaloids)
MainlyMainly
EphedrineEphedrine
PseudoephidrinePseudoephidrine
ephedradines –ephedradines –
hypotensivehypotensive
propertiesproperties

Ephedra - UsesEphedra - Uses
Asthma, colds, flu andAsthma, colds, flu and
Hayfever medicationsHayfever medications
(action is more prolonged(action is more prolonged
than adrenaline.than adrenaline.
Additional advantage:Additional advantage:
need not be given byneed not be given by
injection, but can beinjection, but can be
administered orally).administered orally).
Allopathic: Sinumed (driesAllopathic: Sinumed (dries
a runny nose)a runny nose)
TCM: Used as an anti-TCM: Used as an anti-
inflammatory.inflammatory.
Weight loss (increasesWeight loss (increases
metabolism, decreasesmetabolism, decreases
appetite – CNS stimulantappetite – CNS stimulant
– acts on adrenergic– acts on adrenergic
receptors)
Above ground parts areAbove ground parts are
normally used, althoughnormally used, although
the roots are better to usethe roots are better to use
(less alkaloids)(less alkaloids)

Ephedra - CAUTIONSEphedra - CAUTIONS
Above-ground partsAbove-ground parts
contain highercontain higher
amounts of alkaloidsamounts of alkaloids
(increase BP)(increase BP)
Side Effects: CausesSide Effects: Causes
tremors,tremors,
nervousness,nervousness,
palpitations &palpitations &
tacchycardia.tacchycardia.
Full medical Hx of pt isFull medical Hx of pt is
required: contra-required: contra-
indicated in DM,indicated in DM,
thyroid disease,thyroid disease,
glycoma, all cardiacglycoma, all cardiac
conditions (includingconditions (including
hypertension)hypertension)

Khat or Abyssinian TeaKhat or Abyssinian Tea
Consists of the freshConsists of the fresh
leaves ofleaves of CathaCatha
edulis.edulis.
Cultivated in AbyssiniaCultivated in Abyssinia
and Arabianand Arabian
peninsula.peninsula.
Contains protoalkaloidsContains protoalkaloids

Khat – Uses and ActionsKhat – Uses and Actions
Traditionally: Fresh leaves areTraditionally: Fresh leaves are
chewed (mental clarity) andchewed (mental clarity) and
used in the same way asused in the same way as
cocoa.cocoa.
Used by students & labourers.Used by students & labourers.
CNS stimulantCNS stimulant
Used to treat depression (bringsUsed to treat depression (brings
about a sense of well-being)about a sense of well-being)
Alleviates sensations of hungerAlleviates sensations of hunger
and fatigue.and fatigue.
Elevates mood, increases mentalElevates mood, increases mental
and physical alertnessand physical alertness
Used as a tea: colds & flu, weightUsed as a tea: colds & flu, weight
loss, menstrual cramps,loss, menstrual cramps,
asthma.asthma.
Not addictive (leaves are chewedNot addictive (leaves are chewed
– juice swallowed – residue– juice swallowed – residue
spat out)spat out)
Toxic in high dosesToxic in high doses
Males: headaches, insomnia, lowMales: headaches, insomnia, low
sperm count, decreasedsperm count, decreased
fertilityfertility
Females: jaundice and acuteFemales: jaundice and acute
gastritisgastritis
(Toxic effects differ in males and(Toxic effects differ in males and
females)females)

Colchicum - LiliaceaeColchicum - Liliaceae
Definition: ColchicumDefinition: Colchicum
seed and corm areseed and corm are
derived from thederived from the
Autumn crocus orAutumn crocus or
meadow saffron,meadow saffron,
ColchicumColchicum
autumnaleautumnale..

ColchicineColchicine
Constituent in colchiumConstituent in colchium
seeds and corm.seeds and corm.
Amorphous, yellow-whiteAmorphous, yellow-white
alkaloid (darkens onalkaloid (darkens on
exposure to light).exposure to light).
Gives a strong yellowGives a strong yellow
coloration with strongcoloration with strong
mineral acids.mineral acids.
Dissolves readily in water,Dissolves readily in water,
alcohol and chloroform,alcohol and chloroform,
but only slightly in etherbut only slightly in ether
or petroleum spirit.or petroleum spirit.
Weak baseWeak base

Colchium UsesColchium Uses
Relieve gout (used withRelieve gout (used with
caution – professionalcaution – professional
supervision)supervision)
Also used in biologicalAlso used in biological
experiments toexperiments to
produce polyploidyproduce polyploidy
(multiplication of the(multiplication of the
chromosomes in achromosomes in a
cell nucleus)cell nucleus)

Purine AlkaloidsPurine Alkaloids
Also known as non-alkaloids (xanthines)Also known as non-alkaloids (xanthines)
* synthetic origin does not contain an intact AA* synthetic origin does not contain an intact AA
* Amphoteric Character* Amphoteric Character
* Peculiar solubility in warm water and in chlorinated* Peculiar solubility in warm water and in chlorinated
solvents.solvents.
Examples are caffeine (seeds of coffee plants, kolaExamples are caffeine (seeds of coffee plants, kola
plants, tea leaves and guarana seeds),plants, tea leaves and guarana seeds),
theobromine (Theobroma cocao) and theophyllinetheobromine (Theobroma cocao) and theophylline
(tea leaves & cola nuts).(tea leaves & cola nuts).
Beverages such as tea and coffee owe their stimulantBeverages such as tea and coffee owe their stimulant
action to the purine alkaloids.action to the purine alkaloids.

Caffeine: stimulates CNSCaffeine: stimulates CNS
and has a weak diureticand has a weak diuretic
action.action.
Theobromine: oppositeTheobromine: opposite
action.action.
Theophylline: relaxesTheophylline: relaxes
involuntary musclesinvoluntary muscles
more effectively thanmore effectively than
caffeine or theobrominecaffeine or theobromine
Caffeine does notCaffeine does not
precipitate like mostprecipitate like most
alkaloids.alkaloids.
A purple colour is derivedA purple colour is derived
from caffeine and otherfrom caffeine and other
purine derivativespurine derivatives
(murexide test).(murexide test).

Pharmacological Activity ofPharmacological Activity of
CaffeineCaffeine
CNS activity, enhancesCNS activity, enhances
alertness, facilitates thoughtalertness, facilitates thought
formation, decreases theformation, decreases the
sensation of fatigue.sensation of fatigue.
Very high doses: inducesVery high doses: induces
nervousness, insomnia &nervousness, insomnia &
tremors.tremors.
Stimulates respiratory centre ofStimulates respiratory centre of
the brain (increasingthe brain (increasing
sensitivity to CO2).sensitivity to CO2).
Cardiovascular activity:Cardiovascular activity:
Positive inotropic action,Positive inotropic action,
causes tacchycardia,causes tacchycardia,
increases CO, slightincreases CO, slight
peripheral dilation, mildperipheral dilation, mild
diuretic actiondiuretic action

Caffeine: UsesCaffeine: Uses
In combinations withIn combinations with
antipyretics andantipyretics and
analgesics, cold andanalgesics, cold and
flu medication.flu medication.
(increases the intestinal(increases the intestinal
absorption of some ofabsorption of some of
these drugs; or tothese drugs; or to
counteractcounteract
drowsiness).drowsiness).
Ingredient in non-Ingredient in non-
alcoholic beveragesalcoholic beverages
and “energizing”and “energizing”
beveragesbeverages

Caffeine Side EffectsCaffeine Side Effects
Sinus tacchycardiaSinus tacchycardia
Epigastric painEpigastric pain
NauseaNausea
VomitingVomiting
HeadachesHeadaches
NervousnessNervousness
InsomniaInsomnia
tremorstremors

Pharmacological Action ofPharmacological Action of
TheophyllineTheophylline
bronchial smooth musclebronchial smooth muscle
relaxantrelaxant
Stimulates respiratoryStimulates respiratory
centre in the brain stemcentre in the brain stem
by increasing sensitivityby increasing sensitivity
to CO2.to CO2.
CNS stimulatingCNS stimulating
Slightly inotropic.Slightly inotropic.
Diuretic activity is strongerDiuretic activity is stronger
than that of caffeine.than that of caffeine.

Theophylline - UsesTheophylline - Uses
Used for cough &Used for cough &
asthmatic medicationasthmatic medication
ReversibleReversible
bronchospasmbronchospasm
(chronic obstructive(chronic obstructive
pulmonary disease).pulmonary disease).

Theophylline Side EffectsTheophylline Side Effects
NervousnessNervousness
SleeplessnessSleeplessness
Transient tacchycaridiaTransient tacchycaridia
Permanent tacchycardiaPermanent tacchycardia
NauseaNausea
VomitingVomiting
HeadachesHeadaches
TremorsTremors
DiarrhoeaDiarrhoea

Theobroma – ActionsTheobroma – Actions
Found in CocoaFound in Cocoa
Nutritive/foodNutritive/food
Nervous systemNervous system
stimulantstimulant
DiureticDiuretic

Theobroma - UsesTheobroma - Uses
Cocao butter is used asCocao butter is used as
a base fora base for
suppositories andsuppositories and
salvessalves
Heart and kidney tonicHeart and kidney tonic
Chocolate (flavouring)Chocolate (flavouring)

Plant Alkaloids

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