alkaloids (1).pdf for pharmacognosy student
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About This Presentation
5
THE MEVALONATE AND
METHYLERYTHRITOL PHOSPHATE
PATHWAYS: TERPENOIDS AND
STEROIDS
Terpenoids form a large and structurally diverse
family of natural products derived from C5 isoprene
units (Figure 5.1) joined in a head-to-tail fashion.
Typical structures contain carbon skeletons represented
by (C5)n...
Slide Content
ALKALOIDS ALKALOIDS
By AbyotE. (B. Pharm,MSc)
By AbyotE. (B. Pharm,MSc)
Learning objectives
•Describe general back ground of alkaloids
–Properties;
–History;
–Distribution; –Distribution;
–Nomenclature;
–Extraction method;
–Classification;
–Chemical test
•Describe general back ground of alkaloids
–Properties;
–History;
–Distribution; –Distribution;
–Nomenclature;
–Extraction method;
–Classification;
–Chemical test
–Discuss crude drug contain alkaloids along with
their biological source, major chemical
constituents, clinical /pharmaceutical use
–Categorize alkaloids according to their Categorize alkaloids according to their
biosynthesis root, chemical class, taxonomic class
and pharmacologic action
their biological source, major chemical
constituents, clinical /pharmaceutical use
–Categorize alkaloids according to their Categorize alkaloids according to their
biosynthesis root, chemical class, taxonomic class
and pharmacologic action
Introduction
•Are organic nitrogenous bases found mainly in
plants, but also to a lesser extent in
microorganisms and animals
•'alkaloid‘----alkali-like•'alkaloid‘----alkali-like
•A precise definition is somewhat difficult
because there is no clear-cut boundary
between alkaloids and naturally occurring
complex amines
•Are organic nitrogenous bases found mainly in
plants, but also to a lesser extent in
microorganisms and animals
•'alkaloid‘----alkali-like•'alkaloid‘----alkali-like
•A precise definition is somewhat difficult
because there is no clear-cut boundary
between alkaloids and naturally occurring
complex amines
Introduction…
•Typical alkaloids are:
–Derived from plant sources
–They are basic.
–They contain one or more nitrogen atom/s –They contain one or more nitrogen atom/s
(usually in a heterocyclic ring) and they usually
have a marked physiological action on man or
other animals
•Typical alkaloids are:
–Derived from plant sources
–They are basic.
–They contain one or more nitrogen atom/s –They contain one or more nitrogen atom/s
(usually in a heterocyclic ring) and they usually
have a marked physiological action on man or
other animals
History
•The French apothecary Derosneisolated the
alkaloid known as narcotinein 1803 and
•The Hanoverian apothecary Serttilnerfurther
reinvestigated opium and isolated morphinereinvestigated opium and isolated morphine
•The French apothecary Derosneisolated the
alkaloid known as narcotinein 1803 and
•The Hanoverian apothecary Serttilnerfurther
reinvestigated opium and isolated morphinereinvestigated opium and isolated morphine
History…
•Isolation of other alkaloids particularly by
Pelletier and Caventou, rapidly followed:
–Strychnine (1817)
–emetine (1817)–emetine (1817)
–brucine(1819)
–pipcrine(1819)
–caffeine (1819), quinine (1820)
–colchicine( I 820)
–coniine ( I 826)
•Isolation of other alkaloids particularly by
Pelletier and Caventou, rapidly followed:
–Strychnine (1817)
–emetine (1817)–emetine (1817)
–brucine(1819)
–pipcrine(1819)
–caffeine (1819), quinine (1820)
–colchicine( I 820)
–coniine ( I 826)
History…
•Coniine was the first alkaloid to have its
structure established and to be synthesized
–Modern methods and instrumentation have
greatly facilitated these investigations note that greatly facilitated these investigations note that
the yields of
•'minor‘ alkaloids, during the first quarter of the last
century would now be sufficient, several thousand time
for a complete structural analysis
•Coniine was the first alkaloid to have its
structure established and to be synthesized
–Modern methods and instrumentation have
greatly facilitated these investigations note that greatly facilitated these investigations note that
the yields of
•'minor‘ alkaloids, during the first quarter of the last
century would now be sufficient, several thousand time
for a complete structural analysis
History…
•In the second half of the twentieth century
alkaloids feature strongly in the search for
plant drugs with anticancer activity
–A notable success was the introduction of –A notable success was the introduction of
Catharanthusalkaloids and paclitaxel
–There is much current interest in other alkaloids
having anticancer propertiesas well as those
exhibiting anti-agingand antiviral possibilities
•In the second half of the twentieth century
alkaloids feature strongly in the search for
plant drugs with anticancer activity
–A notable success was the introduction of –A notable success was the introduction of
Catharanthusalkaloids and paclitaxel
–There is much current interest in other alkaloids
having anticancer propertiesas well as those
exhibiting anti-agingand antiviral possibilities
Distribution
•In the fungi thelysergic acid derivatives and
the sulphur' containing alkaloids.
e .g. the gliotoxins
•Among the pteridophytesand gymnosperms •Among the pteridophytesand gymnosperms
–lycopodium, ephedrine and Taxusalkaloids have
medicinal interest
•In the fungi thelysergic acid derivatives and
the sulphur' containing alkaloids.
e .g. the gliotoxins
•Among the pteridophytesand gymnosperms •Among the pteridophytesand gymnosperms
–lycopodium, ephedrine and Taxusalkaloids have
medicinal interest
Distribution...
•Chiefly occur in certain dicotyledon.
–The alkaloids occur in the leaf, root, bark, and
seeds of nearly 40 plant family
•Lauraceae,, Magnoliaceae, Berberidaceae, •Lauraceae,, Magnoliaceae, Berberidaceae,
Menispermaceae, Ranunculaceae, Papaveraceae,
Rutaceae, Apocynaceae, Loganiaceae, Rubiaceae,
Boragiraceae, Solanaceaea
•Chiefly occur in certain dicotyledon.
–The alkaloids occur in the leaf, root, bark, and
seeds of nearly 40 plant family
•Lauraceae,, Magnoliaceae, Berberidaceae, •Lauraceae,, Magnoliaceae, Berberidaceae,
Menispermaceae, Ranunculaceae, Papaveraceae,
Rutaceae, Apocynaceae, Loganiaceae, Rubiaceae,
Boragiraceae, Solanaceaea
Distribution...
•Nearly 300 alkaloids
belonging to more than 24
classes of alkaloids are
known to occur in the skins known to occur in the skins
of amphibians along with
other toxins
•the potent neurotoxin
alkaloids of frogs from the
genus Phyllobates, which
are among some of the most
poisonous substances known
•Other reptilian alkaloids are
strongly antimicrobial
•Nearly 300 alkaloids
belonging to more than 24
classes of alkaloids are
known to occur in the skins known to occur in the skins
of amphibians along with
other toxins
•the potent neurotoxin
alkaloids of frogs from the
genus Phyllobates, which
are among some of the most
poisonous substances known
•Other reptilian alkaloids are
strongly antimicrobial
Distribution...
•Alkaloids derived from mammals include
Indoleand isoquinolineclasses along with
mammalian morphine.
•A few are found in both plants and animals•A few are found in both plants and animals
•Alkaloids derived from mammals include
Indoleand isoquinolineclasses along with
mammalian morphine.
•A few are found in both plants and animals•A few are found in both plants and animals
Properties
•Most alkaloids are well-defined crystalline
substances which unite with acids to form salts
•In the plant they may exist in the free state, as
salts or as N-oxides
•In addition to the elements carbon, hydrogen and •In addition to the elements carbon, hydrogen and
nitrogen, most alkaloids contain oxygen
–A few, such as coniine and nicotine , are oxygen-free
and are liquids
•Almost colourless but few coloured found
Example berberineis yellow
•Most alkaloids are well-defined crystalline
substances which unite with acids to form salts
•In the plant they may exist in the free state, as
salts or as N-oxides
•In addition to the elements carbon, hydrogen and •In addition to the elements carbon, hydrogen and
nitrogen, most alkaloids contain oxygen
–A few, such as coniine and nicotine , are oxygen-free
and are liquids
•Almost colourless but few coloured found
Example berberineis yellow
Properties…
•They are almost bitter in taste and optically
active
•Free bases are insoluble or sparingly soluble in
water but soluble in organic solventswater but soluble in organic solvents
•The salt being usually soluble in water but
sparingly soluble in organic solvents
•e. g. strychnine hydrochloride is much more
soluble in water than is strychnine base.
•They are almost bitter in taste and optically
active
•Free bases are insoluble or sparingly soluble in
water but soluble in organic solventswater but soluble in organic solvents
•The salt being usually soluble in water but
sparingly soluble in organic solvents
•e. g. strychnine hydrochloride is much more
soluble in water than is strychnine base.
Properties…
•Knowledge of the solubility of alkaloids and
their salts is of considerable pharmaceutical
importance
–These differences in solubility between alkaloids –These differences in solubility between alkaloids
and their salts provide methods for the isolation
•Knowledge of the solubility of alkaloids and
their salts is of considerable pharmaceutical
importance
–These differences in solubility between alkaloids –These differences in solubility between alkaloids
and their salts provide methods for the isolation
Properties…
•Many exceptions to the above generalizations
–Caffeine (base) being readily extracted from tea
with water and colchicines are being soluble in
either acid, neutral or alkaline watereither acid, neutral or alkaline water
–Some alkaloidalsalts are sparingly soluble in water
•Quinine sulphate sparingly soluble in water
•Many exceptions to the above generalizations
–Caffeine (base) being readily extracted from tea
with water and colchicines are being soluble in
either acid, neutral or alkaline watereither acid, neutral or alkaline water
–Some alkaloidalsalts are sparingly soluble in water
•Quinine sulphate sparingly soluble in water
Nomenclature of Alkaloids
•Alkaloids can be named by:
–The plants from which they are obtained
•A large majority have been named based on this.
•e.gPapaverinefrom Papaversomniferum
•From their physiologic response•From their physiologic response
–Emetine (in Greek mean-vomit),
–Morphine (in Germany mean-god of dream)
•Name given after the discoverer
–Only a single alkaloid is named
•Pelletierinehas been named after its discoverer PJ-Pelletier
•Alkaloids can be named by:
–The plants from which they are obtained
•A large majority have been named based on this.
•e.gPapaverinefrom Papaversomniferum
•From their physiologic response•From their physiologic response
–Emetine (in Greek mean-vomit),
–Morphine (in Germany mean-god of dream)
•Name given after the discoverer
–Only a single alkaloid is named
•Pelletierinehas been named after its discoverer PJ-Pelletier
Role of Alkaloids in plant
•As a reserve substance with an ability to
supply nitrogen.
•As a defensive mechanism for plant growing in
dry region dry region
•As a regulatory growth factors in plants
•Carriers with in plants for transportation of
growth acids
•As a reserve substance with an ability to
supply nitrogen.
•As a defensive mechanism for plant growing in
dry region dry region
•As a regulatory growth factors in plants
•Carriers with in plants for transportation of
growth acids
Extraction of alkaloids
•Using a modified version of the classic ‘‘acid–
base shakeout’’ method
–Mineral acids and strong bases should be avoided
in extracting alkaloids (and plant material in in extracting alkaloids (and plant material in
general) because of the risk of artefact formation
•Using a modified version of the classic ‘‘acid–
base shakeout’’ method
–Mineral acids and strong bases should be avoided
in extracting alkaloids (and plant material in in extracting alkaloids (and plant material in
general) because of the risk of artefact formation
Plant material
DefatedMeOH
extract
Saturate with water
Suspend in tartaric acid at PH 5
Defat, extract,
concenterate
Aqueous phase
EtOAClayer
Contains, primary, secondary
and tertiary amines
Aqueous layer
(quaternary amine, N-
Oxides)
Make alkaline with Na
2CO
3
Partition with EtOAC
EtOAcphase
Suspend in tartaric acid at PH 5
Partition with EtOAc
DefatedMeOH
extract
Saturate with water
Suspend in tartaric acid at PH 5
Defat, extract,
concenterate
Aqueous phase
EtOAClayer
Contains, primary, secondary
and tertiary amines
Aqueous layer
(quaternary amine, N-
Oxides)
Make alkaline with Na
2CO
3
Partition with EtOAC
EtOAcphase
Suspend in tartaric acid at PH 5
Partition with EtOAc
Classification
•Varies classifications of alkaloids are:
–Pharmacological classification:
CNS-stimulant, sympathomimetic,antiprotozolal,
analgesics etc.
–Taxonomical classification: based on their distribution –Taxonomical classification: based on their distribution
on various plant families. Like Solanaceae,
Leguminaceae, Lamiaceae
–Biosynthetic classification: Based on the precursor
from which the alkaloidaldrug biosynthesized in the
plant
e.gornithininederived , tyrosine derived, phenyl
alanine..etc.
•Varies classifications of alkaloids are:
–Pharmacological classification:
CNS-stimulant, sympathomimetic,antiprotozolal,
analgesics etc.
–Taxonomical classification: based on their distribution –Taxonomical classification: based on their distribution
on various plant families. Like Solanaceae,
Leguminaceae, Lamiaceae
–Biosynthetic classification: Based on the precursor
from which the alkaloidaldrug biosynthesized in the
plant
e.gornithininederived , tyrosine derived, phenyl
alanine..etc.
Classification ---
•Chemical classification:
–It is based on fundamental ring structure
–The alkalidal drugs are broadly categorized in to three
i.True alkaloids –contain nitrogen in a hetrocyclicring and
biogenetically derived from amino acids. Eg. Tropanebiogenetically derived from amino acids. Eg. Tropane
alkaloids, Indolealkaloids,
ii.Proto /Amino alkaloids:
–biosyntheszedfrom amino acids but devoid of hetrocyclicnitrogen
–Eg. Biological amines, Ephedraalkalods, Khatalkaloids
iii. Pseudo alkaloids
May Have hetrocyclicnitrogen but not biosynthesized from amino
acids
Eg. Purinealkaloids, Terpenoidalalkaloids, Steroidal alkaloids
•Chemical classification:
–It is based on fundamental ring structure
–The alkalidal drugs are broadly categorized in to three
i.True alkaloids –contain nitrogen in a hetrocyclicring and
biogenetically derived from amino acids. Eg. Tropanebiogenetically derived from amino acids. Eg. Tropane
alkaloids, Indolealkaloids,
ii.Proto /Amino alkaloids:
–biosyntheszedfrom amino acids but devoid of hetrocyclicnitrogen
–Eg. Biological amines, Ephedraalkalods, Khatalkaloids
iii. Pseudo alkaloids
May Have hetrocyclicnitrogen but not biosynthesized from amino
acids
Eg. Purinealkaloids, Terpenoidalalkaloids, Steroidal alkaloids
Chemical Test
Reagent/test Compositionofthereagent Result
Meyer’sreagent PotassiummercuriciodidesolutionCreamprecipitate
Wagner’sreagent Iodineinpotassiumiodide Reddish-brownprecipitate
Tannicacid Tannicacid Precipitation
Hager’sreagent Asaturatedsolutionofpicricacid Yellowprecipitate
Dragendorff’s
reagent
Solutionofpotassiumbismuth
iodide
Orangeorreddish-brown
precipitate(exceptwithcaffeineandafew
otheralkaloids)
Reagent/test Compositionofthereagent Result
Meyer’sreagent PotassiummercuriciodidesolutionCreamprecipitate
Wagner’sreagent Iodineinpotassiumiodide Reddish-brownprecipitate
Tannicacid Tannicacid Precipitation
Hager’sreagent Asaturatedsolutionofpicricacid Yellowprecipitate
Dragendorff’s
reagent
Solutionofpotassiumbismuth
iodide
Orangeorreddish-brown
precipitate(exceptwithcaffeineandafew
otheralkaloids)
Chemical test…
•Caffeine and other purinederivatives can be
detected by the Muroxidetest.
–Alkaloids are mixed with a tiny amount of
potassium chlorate and a drop of hydrochloric potassium chlorate and a drop of hydrochloric
acid and evaporated to dryness, and the resulting
residue is exposed to ammonia vapour.
•Purinealkaloids produce pink colour in this test
•Caffeine and other purinederivatives can be
detected by the Muroxidetest.
–Alkaloids are mixed with a tiny amount of
potassium chlorate and a drop of hydrochloric potassium chlorate and a drop of hydrochloric
acid and evaporated to dryness, and the resulting
residue is exposed to ammonia vapour.
•Purinealkaloids produce pink colour in this test
INDOLE ALKALOIDSINDOLE ALKALOIDS
Learning objectives
•After completing this session you will be able
to:
–Distinguish the basic skeletal of indolealkaloids
and its their biosynthesis root and its their biosynthesis root
–List type of indolealkaloids
–Discuss clinically important drug containing indole
alkaloids
•After completing this session you will be able
to:
–Distinguish the basic skeletal of indolealkaloids
and its their biosynthesis root and its their biosynthesis root
–List type of indolealkaloids
–Discuss clinically important drug containing indole
alkaloids
IndoleAlkaloids
•Incorporate an indolering system in their
molecular structure
•Biogenetically derived from tryptophan
–contain two nitrogen atoms, one of which is –contain two nitrogen atoms, one of which is
contained within the five-memberedpart of the
indolenucleus
•Incorporate an indolering system in their
molecular structure
•Biogenetically derived from tryptophan
–contain two nitrogen atoms, one of which is –contain two nitrogen atoms, one of which is
contained within the five-memberedpart of the
indolenucleus
Type of IndoleAlkaloids
•The simple indoles
Tryptamine psilocybin
•The simple indoles
Tryptamine psilocybin
Type….
•Simple β-Carboline
•Simple β-Carboline
Type….
•Complex indole
–the tryptophan skeleton is linked with a
monoterpeneunit derived from the iridoid
secologanin.secologanin.
•Complex indole
–the tryptophan skeleton is linked with a
monoterpeneunit derived from the iridoid
secologanin.secologanin.
•E.g. Ajmalicine
Ergot
•Dried sclerotiumof the
fungus Claviceps
purpurea
(Clavicipitaceae)
developed on the ovary developed on the ovary
of rye, Secalecereale
(Poaceae)
•Dried sclerotiumof the
fungus Claviceps
purpurea
(Clavicipitaceae)
developed on the ovary developed on the ovary
of rye, Secalecereale
(Poaceae)
Ergot...
•Cultivated in Czech Republic, Germany,
Hungary, Switzerland, Austria, and Poland
•Cultivated in Czech Republic, Germany,
Hungary, Switzerland, Austria, and Poland
The phenomena of Ergotism
Ergot...
•Constituent
–The medicinally useful compounds are derivatives
of (+)-lysergic acid
•Constituent
–The medicinally useful compounds are derivatives
of (+)-lysergic acid
Ergot...
•Water soluble
component
–The water-soluble amino
alcohol derivatives (up
to about 20% of the total to about 20% of the total
alkaloids)
–Ergometrine
(ergonovine) is an amide
of lysergic acid and 2-
aminopropanol
•Water soluble
component
–The water-soluble amino
alcohol derivatives (up
to about 20% of the total to about 20% of the total
alkaloids)
–Ergometrine
(ergonovine) is an amide
of lysergic acid and 2-
aminopropanol
Ergot...
•Water-insoluble peptide
derivatives (up to 80%
of the total alkaloids).
–Contain a cyclized
tripeptidefragment tripeptidefragment
bonded to lysergic acid
via an amide linkage
•ergotamine group
•Water-insoluble peptide
derivatives (up to 80%
of the total alkaloids).
–Contain a cyclized
tripeptidefragment tripeptidefragment
bonded to lysergic acid
via an amide linkage
•ergotamine group
Ergot...
•Chemical test
–Vanurk’sreagent: paradimethylamino
benzoldehyde
•Chemical test
–Vanurk’sreagent: paradimethylamino
benzoldehyde
Ergot...
•Uses:
–Ergometrineis mainly used in childbirth
•cause contraction of the uterus and contract blood
vessels, thus reducing bleeding.vessels, thus reducing bleeding.
–Ergotamine has a stronger dopaminergic
•mainly employed in treating migraine because it
reduces vasodilation
•Uses:
–Ergometrineis mainly used in childbirth
•cause contraction of the uterus and contract blood
vessels, thus reducing bleeding.vessels, thus reducing bleeding.
–Ergotamine has a stronger dopaminergic
•mainly employed in treating migraine because it
reduces vasodilation
Ergot...
•LSD
–is a semisyntheticderivative and possesses
psychomimeticaction
•LSD
–is a semisyntheticderivative and possesses
psychomimeticaction
Nux vomica (Poison nut)
•Consists of the dried ripe seeds of Strychnos
nux-vomica(Loganiaceae), a small tree found
in a wide area of East Asia
•Consists of the dried ripe seeds of Strychnos
nux-vomica(Loganiaceae), a small tree found
in a wide area of East Asia
Nux vomica...
•Constituents:
–These seeds contain 1.5–
5% of alkaloids
•chiefly strychnine(about
1.2%) and brucine1.2%) and brucine
(about1.6%).
•Constituents:
–These seeds contain 1.5–
5% of alkaloids
•chiefly strychnine(about
1.2%) and brucine1.2%) and brucine
(about1.6%).
Nux vomica...
•Strychnine
–is very toxic, affecting the CNS and causing
convulsion
•It has found use as a vermin killer•It has found use as a vermin killer
•Its only medicinal use is in very small doses as an
appetite stimulant and general tonic, sometimes with
iron salts if the patient is anaemic
•Strychnine
–is very toxic, affecting the CNS and causing
convulsion
•It has found use as a vermin killer•It has found use as a vermin killer
•Its only medicinal use is in very small doses as an
appetite stimulant and general tonic, sometimes with
iron salts if the patient is anaemic
Nux vomica...
•Brucine
–is considerably less toxic
–It is used to denaturing alcohol and inedible fats.
•Brucine
–is considerably less toxic
–It is used to denaturing alcohol and inedible fats.
Physostigma(Calabarbean)
•Is a perennial woody climbing plant obtained
from Physostigmavenenosum(Fabaceae)
found on the banks of streams in West Africa
•Is a perennial woody climbing plant obtained
from Physostigmavenenosum(Fabaceae)
found on the banks of streams in West Africa
Physostigma...
•Constituents:
–The seeds contain
several alkaloids
(alkaloid content about
1.5%), 1.5%),
•Physostigmineis the chief
•Constituents:
–The seeds contain
several alkaloids
(alkaloid content about
1.5%), 1.5%),
•Physostigmineis the chief
Physostigma...
•Uses:
–Physostigmine: is a reversible inhibitor of
cholinesterase
•Its major use is as a miotic, to contract the pupil of the •Its major use is as a miotic, to contract the pupil of the
eye, often to combat the effect of mydriaticssuch as
atropine
•It also reduces intraocular pressure in the eye by
increasing outflow of the aqueous humour, and is a
valuable treatment for glaucoma, often in combination
with pilocarpine
•Uses:
–Physostigmine: is a reversible inhibitor of
cholinesterase
•Its major use is as a miotic, to contract the pupil of the •Its major use is as a miotic, to contract the pupil of the
eye, often to combat the effect of mydriaticssuch as
atropine
•It also reduces intraocular pressure in the eye by
increasing outflow of the aqueous humour, and is a
valuable treatment for glaucoma, often in combination
with pilocarpine
Physostigma...
•Physostigminecan be used as an antidote to
anticholinergicpoisons such as atropine
•Physostigminecan be used as an antidote to
anticholinergicpoisons such as atropine
Physostigma...
•Anticholinesterasedrugs are also of value in the
treatment of Alzheimer’s disease,
•Use of acetylcholinesteraseinhibitors can result in
significant memory enhancement in patients, and
analogues of physostigmineare presently in use analogues of physostigmineare presently in use
(e.g.rivastigmine)
•Anticholinesterasedrugs are also of value in the
treatment of Alzheimer’s disease,
•Use of acetylcholinesteraseinhibitors can result in
significant memory enhancement in patients, and
analogues of physostigmineare presently in use analogues of physostigmineare presently in use
(e.g.rivastigmine)
Rauwolfia
•the dried rhizome and
roots of Rauwolfia
serpentine
(Apocynaceae), a small
shrub from India, shrub from India,
Pakistan, Burma, and
Thailand
•Otherspecies used in
commerce include R.
vomitoriafrom tropical
Africa
•the dried rhizome and
roots of Rauwolfia
serpentine
(Apocynaceae), a small
shrub from India, shrub from India,
Pakistan, Burma, and
Thailand
•Otherspecies used in
commerce include R.
vomitoriafrom tropical
Africa
Rauwolfia...
•Constituent
–Therapeutically active
compounds
•Reserpine
•Rescinnamine•Rescinnamine
•deserpidine
•Constituent
–Therapeutically active
compounds
•Reserpine
•Rescinnamine•Rescinnamine
•deserpidine
Rauwolfia...
•Use:
–Reserpineand deserpidinehave been widely used
as antihypertensivesand mild tranquillizers
–They act by interfering with catecholamine –They act by interfering with catecholamine
storage, depleting levels of available
neurotransmitters
•Reserpinehas also been suggested to play a role in the
promotion of breast cancers.
•Use:
–Reserpineand deserpidinehave been widely used
as antihypertensivesand mild tranquillizers
–They act by interfering with catecholamine –They act by interfering with catecholamine
storage, depleting levels of available
neurotransmitters
•Reserpinehas also been suggested to play a role in the
promotion of breast cancers.
Vinca
•The Madagascar
periwinkle Catharanthus
roseus(Apocynaceae) is a
small herb or shrub
originating in Madagascaroriginating in Madagascar
•Drug material is now
cultivated in many parts
of the world, including
the USA, Europe, India,
Australia, and South
America.
•The Madagascar
periwinkle Catharanthus
roseus(Apocynaceae) is a
small herb or shrub
originating in Madagascaroriginating in Madagascar
•Drug material is now
cultivated in many parts
of the world, including
the USA, Europe, India,
Australia, and South
America.
Vinca…
•constituents
–Vinblastine
–Vincristine
–ajmalicine
–serpentine
•constituents
–Vinblastine
–Vincristine
–ajmalicine
–serpentine
Vinca…
•Uses:
–Vinblastineis used mainly in the treatment of
Hodgkin’s disease
–Vincristinehas superior antitumouractivity –Vincristinehas superior antitumouractivity
compared to vinblastinebut is more neurotoxic
–Some other cancer conditions, including
lymphomas, small celllung cancer, and cervical
and breast cancers, also respond favourably
•Uses:
–Vinblastineis used mainly in the treatment of
Hodgkin’s disease
–Vincristinehas superior antitumouractivity –Vincristinehas superior antitumouractivity
compared to vinblastinebut is more neurotoxic
–Some other cancer conditions, including
lymphomas, small celllung cancer, and cervical
and breast cancers, also respond favourably
ISOQUINOLINE ALKALOIDSISOQUINOLINE ALKALOIDS
Learning objectives
•After completing this unit you will be able to:
–Distinguish the basic skeletal and biosynthetic root
of isoquinoline alkaloids
–Discuss clinically important crude drug containing
isoquinoline alkaloids (Opium, Curare, isoquinoline alkaloids (Opium, Curare,
Ipicacuhana)
•After completing this unit you will be able to:
–Distinguish the basic skeletal and biosynthetic root
of isoquinoline alkaloids
–Discuss clinically important crude drug containing
isoquinoline alkaloids (Opium, Curare, isoquinoline alkaloids (Opium, Curare,
Ipicacuhana)
Isoquinoline
•Belongs alkaloids having isoquinolineor
tetrahydroisoquinolinering
•Biogenetically from phenylalanine group or its
hydroxyderivative—tyrosine hydroxyderivative—tyrosine
•Belongs alkaloids having isoquinolineor
tetrahydroisoquinolinering
•Biogenetically from phenylalanine group or its
hydroxyderivative—tyrosine hydroxyderivative—tyrosine
Opium
•Air dried milky latex
obtained by incision
from the unripe capsule
of Papaversomniferum
(Papaveraceae)
•Opium poppy yields
seeds, which are used
in baking and are also
pressed to give poppy
seed oil
•Air dried milky latex
obtained by incision
from the unripe capsule
of Papaversomniferum
(Papaveraceae)
•Opium poppy yields
seeds, which are used
in baking and are also
pressed to give poppy
seed oil
Opium…
•The main producer of medicinal opium is
India, while poppy straw is cultivated in
Turkey, Russia, and Australia
•Opium black market•Opium black market
–Golden Triangle (Burma/Myanmar, Laos, and
Thailand),
–Golden Crescent (Iran, Pakistan, and Afghanistan),
and Mexico
•The main producer of medicinal opium is
India, while poppy straw is cultivated in
Turkey, Russia, and Australia
•Opium black market•Opium black market
–Golden Triangle (Burma/Myanmar, Laos, and
Thailand),
–Golden Crescent (Iran, Pakistan, and Afghanistan),
and Mexico
Opium…
•Constituent:
–Opium contains some 30
alkaloids, which are
largely combined with
the organic acid meconic
acidacid
•Constituent:
–Opium contains some 30
alkaloids, which are
largely combined with
the organic acid meconic
acidacid
Opium…
•Benzyl isoquinoline
type
•Papaverine
•Noscapine
•Narceine•Narceine
•Benzyl isoquinoline
type
•Papaverine
•Noscapine
•Narceine•Narceine
Opium…
•Phenanthrenetype
–Morphine
–Condeine
–Thebaine
•Phenanthrenetype
–Morphine
–Condeine
–Thebaine
Opium…
•Use:
–Opium belongs to the category of hypnotic,
sedative and analgesic in which the action is
mainly due to morphine
•Use:
–Opium belongs to the category of hypnotic,
sedative and analgesic in which the action is
mainly due to morphine
Opium…
•Morphine
–is a powerful analgesic and narcotic, and remains
one of the most valuable analgesics for relief of
severe pain.
–It also induces a state of euphoria and mental –It also induces a state of euphoria and mental
detachment, together with nausea, vomiting,
constipation, tolerance, and addiction
•Morphine
–is a powerful analgesic and narcotic, and remains
one of the most valuable analgesics for relief of
severe pain.
–It also induces a state of euphoria and mental –It also induces a state of euphoria and mental
detachment, together with nausea, vomiting,
constipation, tolerance, and addiction
Opium…
•Codeine
–3-O-methyl ether of
morphine
–Codeine is a relatively safe
non-addictive medium
analgesic, but is still too analgesic, but is still too
constipating for long-term
use
–It also has valuable
antitussive action, helping
to relieve and prevent
coughing
•Codeine
–3-O-methyl ether of
morphine
–Codeine is a relatively safe
non-addictive medium
analgesic, but is still too analgesic, but is still too
constipating for long-term
use
–It also has valuable
antitussive action, helping
to relieve and prevent
coughing
Opium…
•Thebaine
–differs structurally from
morphine/codeine mainly
by its possession of a
conjugated dienering
system
–It is almost devoid of –It is almost devoid of
analgesic activity
–may be used as a morphine
antagonist
–Its main value is as
substrate for the semi-
synthesis of other drugs
•Thebaine
–differs structurally from
morphine/codeine mainly
by its possession of a
conjugated dienering
system
–It is almost devoid of –It is almost devoid of
analgesic activity
–may be used as a morphine
antagonist
–Its main value is as
substrate for the semi-
synthesis of other drugs
Opium…
•Diamorphineor heroin
–is the semi-synthetic (diacetate) of morphine
•Is a highly addictive, analgesic and hypnotic.
•The increased lipophiliccharacter results in better
transport and absorption
•Diamorphineor heroin
–is the semi-synthetic (diacetate) of morphine
•Is a highly addictive, analgesic and hypnotic.
•The increased lipophiliccharacter results in better
transport and absorption
Opium…
•‘opioids’: Semi-synthetic or totally synthetic
morphine-like derivatives:
–etorphine, are used in veterinary practice to
sedate large animals. sedate large animals.
•5000–10,000 times more potent than morphine
•‘opioids’: Semi-synthetic or totally synthetic
morphine-like derivatives:
–etorphine, are used in veterinary practice to
sedate large animals. sedate large animals.
•5000–10,000 times more potent than morphine
Opium…
•Papaverine
–It has little or no analgesic or hypnotic properties
–possesses spasmolyticand vasodilator activity
–It has been used in some expectorant preparations, and in the
treatment of gastrointestinal spasms, but its efficacy was not
substantiated
–It is sometimes used as an effective treatment for male impotence, –It is sometimes used as an effective treatment for male impotence,
being administered by direct injection to achieve erection of the penis
•Papaverine
–It has little or no analgesic or hypnotic properties
–possesses spasmolyticand vasodilator activity
–It has been used in some expectorant preparations, and in the
treatment of gastrointestinal spasms, but its efficacy was not
substantiated
–It is sometimes used as an effective treatment for male impotence, –It is sometimes used as an effective treatment for male impotence,
being administered by direct injection to achieve erection of the penis
Opium…
•Noscapine/Narcotine
–Has good antitussive and
cough suppressant
activity comparable to
that of codeine.
–In recent studies, –In recent studies,
antitumouractivity has
been noted from
noscapine, which binds
to tubulin, thus arresting
cells at mitosis
•Noscapine/Narcotine
–Has good antitussive and
cough suppressant
activity comparable to
that of codeine.
–In recent studies, –In recent studies,
antitumouractivity has
been noted from
noscapine, which binds
to tubulin, thus arresting
cells at mitosis
Opium…
•Papaveretum
–a mixture of purified opium alkaloids, as their
hydrochlorides, and is formulated to contain only
morphine (85.5%), codeine (7.8%), and
papaverine(6.7%)papaverine(6.7%)
–It is used for pain relief during operations
•Papaveretum
–a mixture of purified opium alkaloids, as their
hydrochlorides, and is formulated to contain only
morphine (85.5%), codeine (7.8%), and
papaverine(6.7%)papaverine(6.7%)
–It is used for pain relief during operations
Curare (South American Arrow Poison)
•Curare' is a generic one
applied to various South
American arrow poisons
•Curare' is a generic one
applied to various South
American arrow poisons
Curare…
•Extracts are made from a number of different
plants, particularly members of the
Menispermaceae(e.g.Chondrodendron) and
the Loganiaceae(e.g. Strychnostoxifera)the Loganiaceae(e.g. Strychnostoxifera)
–The principal ones used in curare are
Chondrodendrontomentosom
•Extracts are made from a number of different
plants, particularly members of the
Menispermaceae(e.g.Chondrodendron) and
the Loganiaceae(e.g. Strychnostoxifera)the Loganiaceae(e.g. Strychnostoxifera)
–The principal ones used in curare are
Chondrodendrontomentosom
Curare…
•Constituents:
–The alkaloid content of curare is from 4%
to 7%
–bisbenzyltetrahydroisoquinoline–bisbenzyltetrahydroisoquinoline
•(+) tubocurarine
•It is a mono quaternary ammonium salt,
and is water soluble
•Constituents:
–The alkaloid content of curare is from 4%
to 7%
–bisbenzyltetrahydroisoquinoline–bisbenzyltetrahydroisoquinoline
•(+) tubocurarine
•It is a mono quaternary ammonium salt,
and is water soluble
Curare…
•Other main alkaloids include non-quaternary
dimericstructures such as:
–isochondrodendrineand
–curine(bebeerine)–curine(bebeerine)
•Other main alkaloids include non-quaternary
dimericstructures such as:
–isochondrodendrineand
–curine(bebeerine)–curine(bebeerine)
Curare…
•Uses:
–Tubocurarinechloride, is used to secure muscular
relaxation in surgical operations and in certain
neurological conditionsneurological conditions
•Reducing the need for deep anaesthesia
–limited availability of tubocurarinehas led to the
development of a series of synthetic analogues
•Uses:
–Tubocurarinechloride, is used to secure muscular
relaxation in surgical operations and in certain
neurological conditionsneurological conditions
•Reducing the need for deep anaesthesia
–limited availability of tubocurarinehas led to the
development of a series of synthetic analogues
Ipecacuanha
•Ipecacuanhais obtained
from the dried root or
rhizome and root of
Cephaelisipecacuanha
(Rubiaceae)(Rubiaceae)
–C. ipecacuanhais a
shrub 20-10 cm high
found over a large area
in Brazil.
•It is cultivated to some
extent in Malaysia, Burma
and West Bengal
•Ipecacuanhais obtained
from the dried root or
rhizome and root of
Cephaelisipecacuanha
(Rubiaceae)(Rubiaceae)
–C. ipecacuanhais a
shrub 20-10 cm high
found over a large area
in Brazil.
•It is cultivated to some
extent in Malaysia, Burma
and West Bengal
Ipecacuanha…
•Chemical constituents:
–Emetine and cephaeline
possess a skeleton with two
tetrahydroisoquinolinering
systemssystems
•Chemical constituents:
–Emetine and cephaeline
possess a skeleton with two
tetrahydroisoquinolinering
systemssystems
Ipecacuanha…
–Minor psychotrineand O-methylpsychotrine
–Ipecac also contains ipecacuanicacid, glycoside,
starch and calcium-oxalate
–Minor psychotrineand O-methylpsychotrine
–Ipecac also contains ipecacuanicacid, glycoside,
starch and calcium-oxalate
Ipecacuanha…
•In the treatment of amoebic dysentery
emetine hydrochloride is frequently given by
injection and emetine and bismuth iodide by
mouthmouth
•In the treatment of amoebic dysentery
emetine hydrochloride is frequently given by
injection and emetine and bismuth iodide by
mouthmouth
Ipecacuanha…
•The crude drug extract in the form of
ipecacuanhaemetic mixture is an important
preparation used for drug overdose or
poisoningpoisoning
•The crude drug extract in the form of
ipecacuanhaemetic mixture is an important
preparation used for drug overdose or
poisoningpoisoning
Ipecacuanha…
•O-methyl psychotrinehas displayed fairly low
effects on protein synthesis, but a quite potent
ability to curb viral replication through
inhibition of HIV-reverse transcriptaseinhibition of HIV-reverse transcriptase
–This may give it potential in the treatment of AIDS
•O-methyl psychotrinehas displayed fairly low
effects on protein synthesis, but a quite potent
ability to curb viral replication through
inhibition of HIV-reverse transcriptaseinhibition of HIV-reverse transcriptase
–This may give it potential in the treatment of AIDS
TROPANE ALKALOIDS TROPANE ALKALOIDS
1 + 1=3….WHEN?1 + 1=3….WHEN?
Learning objectives
•After completing this sesionyou will be able
to:
–Distinguish the basic skeletal and biosynthetic root
of tropanealkaloids
–Discuss clinically important crude drug containing
tropanealkaloids (Belladona, Datura, hyosymus,
Coca)
•After completing this sesionyou will be able
to:
–Distinguish the basic skeletal and biosynthetic root
of tropanealkaloids
–Discuss clinically important crude drug containing
tropanealkaloids (Belladona, Datura, hyosymus,
Coca)
Tropane alkaloids
•Ester alkaloids resulted from the coupling of
organic acids with amino alcohol (Base)
•The parent base is the “Tropane” base
•Ester alkaloids resulted from the coupling of
organic acids with amino alcohol (Base)
•The parent base is the “Tropane” base
Tropane…
•Biosynthesized from L-Ornithine
–L-Ornithineis a non-protein amino acid forming
part of the urea cycle in animals, where it is
produced from L-argininein a reaction catalysed
by the enzyme arginaseby the enzyme arginase
–In plants it is formed mainly from L-glutamate
•Biosynthesized from L-Ornithine
–L-Ornithineis a non-protein amino acid forming
part of the urea cycle in animals, where it is
produced from L-argininein a reaction catalysed
by the enzyme arginaseby the enzyme arginase
–In plants it is formed mainly from L-glutamate
Chemical Test
•Vitali-Marin test:
–Tropane alkaloid is treated with fuming HNO
3
followed by evaporation to dryness and addition
of methanolicKOH solution to acetone solution of of methanolicKOH solution to acetone solution of
nitrated residue
–Violet coloration takes place due to tropane
derivatives
•Vitali-Marin test:
–Tropane alkaloid is treated with fuming HNO
3
followed by evaporation to dryness and addition
of methanolicKOH solution to acetone solution of of methanolicKOH solution to acetone solution of
nitrated residue
–Violet coloration takes place due to tropane
derivatives
•TropaneAlkaloids are classified into:
–SolanaceousTropane Alkaloids.
•Occurrence in Atropa, Datura, Hyoscyamus, Duboisia
sppspp
–Erythroxylom: Coca alkaloids
–SolanaceousTropane Alkaloids.
•Occurrence in Atropa, Datura, Hyoscyamus, Duboisia
sppspp
–Erythroxylom: Coca alkaloids
Beladona
•It consists of dried leaves or the leaves and
other aerial parts of Atropabelladonna
(Solanaceae)
•It consists of dried leaves or the leaves and
other aerial parts of Atropabelladonna
(Solanaceae)
•Constituents
–Belladonna herb typically contains 0.3–0.6% of
alkaloids, mainly (−)-hyoscyamine
–Belladonna root has only slightly higher alkaloid –Belladonna root has only slightly higher alkaloid
content at 0.4–0.8%, again mainly (−)hyoscyamine
–Belladonna herb typically contains 0.3–0.6% of
alkaloids, mainly (−)-hyoscyamine
–Belladonna root has only slightly higher alkaloid –Belladonna root has only slightly higher alkaloid
content at 0.4–0.8%, again mainly (−)hyoscyamine
•During extraction hyoscyamineracemizesto
the optically inactive dlAtropine[(±)-
hyoscyamine]
–It is more stable than hyoscyamine–It is more stable than hyoscyamine
–On hydrolysis both yields tropic acid and tropine
the optically inactive dlAtropine[(±)-
hyoscyamine]
–It is more stable than hyoscyamine–It is more stable than hyoscyamine
–On hydrolysis both yields tropic acid and tropine
(−) Hyoscyamine
Atropine
Atropine
•Use
–They are anticholinergicactions
•Used to reduce the secretion such as sweat, saliva and
gastric juice and also to reduce spasmgastric juice and also to reduce spasm
•Decrease saliva and GIT secretions so used as
preoperative.
•Decrease motility of smooth muscles so used as
antispasmodics.
•A mydriatic(causes dilatation of the eye pupil).
–They are anticholinergicactions
•Used to reduce the secretion such as sweat, saliva and
gastric juice and also to reduce spasmgastric juice and also to reduce spasm
•Decrease saliva and GIT secretions so used as
preoperative.
•Decrease motility of smooth muscles so used as
antispasmodics.
•A mydriatic(causes dilatation of the eye pupil).
•An antidote to organophosphorusinsecticides
•It is also sued as an antidote in opium and
chloral hydrate poisoning
•It is also sued as an antidote in opium and
chloral hydrate poisoning
•Homatropineis semi-
synthetic ester of
tropinewith racemic
mandelicacid which is
less toxic than Atropineless toxic than Atropine
•It is used as Mydriatic
with shorter effect than
Atropine
•It has also hypnotic
effect in small doses
synthetic ester of
tropinewith racemic
mandelicacid which is
less toxic than Atropineless toxic than Atropine
•It is used as Mydriatic
with shorter effect than
Atropine
•It has also hypnotic
effect in small doses
•Benzatropine
(benztropine) is an
ether of tropineused as
an antimuscarinicdrug
in the treatment of in the treatment of
Parkinson’s disease
(benztropine) is an
ether of tropineused as
an antimuscarinicdrug
in the treatment of in the treatment of
Parkinson’s disease
Stramonium
•Dried leaves or dried leaves
and flowering tops of Datura
stramoniumandits varieties
(Solanaceae)
•Dried leaves or dried leaves
and flowering tops of Datura
stramoniumandits varieties
(Solanaceae)
•Constituent
–(−)-hyoscyamineand (−)-hyoscinein a ratio of
about 2:1
–In young plants, (−)-hyoscinecan predominate. –In young plants, (−)-hyoscinecan predominate.
–A little atropine may be formed from the
hyoscyamineby racemisation
–(−)-hyoscyamineand (−)-hyoscinein a ratio of
about 2:1
–In young plants, (−)-hyoscinecan predominate. –In young plants, (−)-hyoscinecan predominate.
–A little atropine may be formed from the
hyoscyamineby racemisation
•Hyoscine(C
17H
25O
4N) is an ester of tropic acid
and scopine
17H
25O
4N) is an ester of tropic acid
and scopine
•Use:
–Hyoscinelacks the central stimulant action of
atropine:
•Restricted to sedative properties enable it to be used •Restricted to sedative properties enable it to be used
in the control of motion sickness
–Hyoscinelacks the central stimulant action of
atropine:
•Restricted to sedative properties enable it to be used •Restricted to sedative properties enable it to be used
in the control of motion sickness
Hyosymus
•Hyosymusconsists of
the dried leaves or
leaves and flowering
tops of Hyoscymus
niger(Solonaceae)niger(Solonaceae)
•Hyosymusconsists of
the dried leaves or
leaves and flowering
tops of Hyoscymus
niger(Solonaceae)niger(Solonaceae)
•Constituents:
–Hyoscyamineand hyoscineare the principal
alkaloids
–Henbane resembles belladonna and stramonium–Henbane resembles belladonna and stramonium
in action but is somewhat weaker.
–Hyoscyamineand hyoscineare the principal
alkaloids
–Henbane resembles belladonna and stramonium–Henbane resembles belladonna and stramonium
in action but is somewhat weaker.
Coca leaves
•Are derived from shrubs of
the Erythrorylumcocaand
E. truxillense
(Erythroxylaceae) cultivated
in Peru, Bolivia, Colombia in Peru, Bolivia, Colombia
and Indonesia
•Are derived from shrubs of
the Erythrorylumcocaand
E. truxillense
(Erythroxylaceae) cultivated
in Peru, Bolivia, Colombia in Peru, Bolivia, Colombia
and Indonesia
•constituents:
–cocaine, cinnamyl
cocaine and , α-truxilline
are the most important
–Cocaineon heating at –Cocaineon heating at
160
0
C in conc. HCl
hydrolysedto MeOH,
Benzoic acid and
Ecogoninebase
–cocaine, cinnamyl
cocaine and , α-truxilline
are the most important
–Cocaineon heating at –Cocaineon heating at
160
0
C in conc. HCl
hydrolysedto MeOH,
Benzoic acid and
Ecogoninebase
•Use
–Cocaine was used as local anesthetic.
–Owing to hallucinogenic and additive effects of
cocaine it becomes drug of abuse. cocaine it becomes drug of abuse.
–Several semi synthetic analogue of cocaine are
available
•Procainewas the first major analogue employed.
–Cocaine was used as local anesthetic.
–Owing to hallucinogenic and additive effects of
cocaine it becomes drug of abuse. cocaine it becomes drug of abuse.
–Several semi synthetic analogue of cocaine are
available
•Procainewas the first major analogue employed.
–Benzocaineis used
topically, but has a short
duration of action.
–Tetracaine
oxybuprocaine, and oxybuprocaine, and
proxymetacaineare
valuable local
anaesthticsemployed
principally in ophthalmic
work.
topically, but has a short
duration of action.
–Tetracaine
oxybuprocaine, and oxybuprocaine, and
proxymetacaineare
valuable local
anaesthticsemployed
principally in ophthalmic
work.
•Lidocaine,
•Although introduced as a local anaesthetic, was
subsequently found to be a potent antiarrhythmicagent,
and it now finds further use as an antiarrhythmicdrug
•Although introduced as a local anaesthetic, was
subsequently found to be a potent antiarrhythmicagent,
and it now finds further use as an antiarrhythmicdrug
QUINOLINEALKALOIDSQUINOLINEALKALOIDS
Quinoline
•Have quinolinenucleus in their basic structure
•Modified terpenoidindolealkaloid
•The Cinchona alkaloids are therapeutic
importance of this groupimportance of this group
•Biosynthesized from the amino acid
trypthophan
•Have quinolinenucleus in their basic structure
•Modified terpenoidindolealkaloid
•The Cinchona alkaloids are therapeutic
importance of this groupimportance of this group
•Biosynthesized from the amino acid
trypthophan
Cinchona: Peruvian bark
•is the dried bark from
the stem and root of
species of Cinchona
(Rubiaceae)
•is the dried bark from
the stem and root of
species of Cinchona
(Rubiaceae)
•constituents:
–quinine and quinidine
–Cinchonidineand
cinchonine
–quinine and quinidine
–Cinchonidineand
cinchonine
•Chemical Test:
–Tholleoquintest-the powdered drug gives
emerald green colour with bromine-water and
dilute ammonia solutiondilute ammonia solution
–Tholleoquintest-the powdered drug gives
emerald green colour with bromine-water and
dilute ammonia solutiondilute ammonia solution
•Cinchona bark is antimalarial in nature
•The cinchona preparation like cinchona
extract, compound cinchona tincture etc. are
also employed as bitter stomachics, and also employed as bitter stomachics, and
antipyetics
•Quinidineis the principal cinchona alkaloid
used therapeutically, and is administered to
treat cardiac arrhymias
•The cinchona preparation like cinchona
extract, compound cinchona tincture etc. are
also employed as bitter stomachics, and also employed as bitter stomachics, and
antipyetics
•Quinidineis the principal cinchona alkaloid
used therapeutically, and is administered to
treat cardiac arrhymias
•Causecinchonism
PYRIDINE ALKALOIDS PYRIDINE ALKALOIDS
Pyridine alkaloids
•Have a pyridine nucleus
Biosynthesized from amino acid lysine and/or
tyrosine
•Have a pyridine nucleus
Biosynthesized from amino acid lysine and/or
tyrosine
Lobelia: Indian tobacco
•Lobelia or Indian tobacco consists of the dried
leaves and tops of Lobelia inflate
(Campanulaceae), an annual herb from the
USA and CanadaUSA and Canada
•Lobelia or Indian tobacco consists of the dried
leaves and tops of Lobelia inflate
(Campanulaceae), an annual herb from the
USA and CanadaUSA and Canada
•Constituent:
–Lobeline(lysine derived),
is the chief constituent
–Lobeline(lysine derived),
is the chief constituent
Use
•lobelinestimulates nicotinic receptor sites in a
similar way to nicotine, but with a weaker
effect. effect.
•The crude plant drug has also long been used
to relieveasthma and bronchitis, though in
large doses it can be quite toxic.
•lobelinestimulates nicotinic receptor sites in a
similar way to nicotine, but with a weaker
effect. effect.
•The crude plant drug has also long been used
to relieveasthma and bronchitis, though in
large doses it can be quite toxic.
•Lobelinehas similar physiological effects as
that of nicotine, but weaker so used to
discontinue smoking habit
•An injection of lobelinehydrochloride is used •An injection of lobelinehydrochloride is used
in the resuscitationof new-born infants
that of nicotine, but weaker so used to
discontinue smoking habit
•An injection of lobelinehydrochloride is used •An injection of lobelinehydrochloride is used
in the resuscitationof new-born infants
Arecanuts: Betel nuts.
•Seeds of Areca catechu (Palmae), a tall palm
cultivated in the Indian and Asian continents
•Seeds of Areca catechu (Palmae), a tall palm
cultivated in the Indian and Asian continents
•Constituent.
–Areca contains alkaloids
which are reduced
pyridine derivative .
–arecolineis medicinally –arecolineis medicinally
important
–Areca contains alkaloids
which are reduced
pyridine derivative .
–arecolineis medicinally –arecolineis medicinally
important
•Use:
–Arecolineis parasympathomimeticused for the
treatment of sialogogue(Sialogenous)
–vermicide to eradicate worms in veternary–vermicide to eradicate worms in veternary
medicine.
–Arecolineis parasympathomimeticused for the
treatment of sialogogue(Sialogenous)
–vermicide to eradicate worms in veternary–vermicide to eradicate worms in veternary
medicine.
Tobacco
•The dried leaves of Nicotianatabacum
(Solanaceae)
•The dried leaves of Nicotianatabacum
(Solanaceae)
•Constituent:
–Tobacco leaves contain alkaloids derived from
nicotinic acid.
•From which 0.6–9% of (−)-nicotine, an oily, volatile •From which 0.6–9% of (−)-nicotine, an oily, volatile
liquid alkaloid, together with smaller amounts of
structurally related alkaloids.
•In the leaf, the alkaloids are typically present as salts
with malicand citric acids.
–Tobacco leaves contain alkaloids derived from
nicotinic acid.
•From which 0.6–9% of (−)-nicotine, an oily, volatile •From which 0.6–9% of (−)-nicotine, an oily, volatile
liquid alkaloid, together with smaller amounts of
structurally related alkaloids.
•In the leaf, the alkaloids are typically present as salts
with malicand citric acids.
•Use
–Nicotine in small doses can act as a respiratory
stimulant, though in larger doses it causes
respiratory depression.respiratory depression.
–Powdered tobacco leaves have long been used as
an insecticide, and nicotine has been formulated
for agricultural and horticultural use.
–Nicotine in small doses can act as a respiratory
stimulant, though in larger doses it causes
respiratory depression.respiratory depression.
–Powdered tobacco leaves have long been used as
an insecticide, and nicotine has been formulated
for agricultural and horticultural use.
•Nicotine can improve memory by stimulating
the transmission of nerve impulses, and this
finding may account for the lower incidence of
Alzheimer’s disease in smokersAlzheimer’s disease in smokers
•Polycyclic aromatic hydrocarbons, e.g.benzopyrene,
nitrosamines Are carcinogens
the transmission of nerve impulses, and this
finding may account for the lower incidence of
Alzheimer’s disease in smokersAlzheimer’s disease in smokers
•Polycyclic aromatic hydrocarbons, e.g.benzopyrene,
nitrosamines Are carcinogens
•Tobacco smoke contains over 4000 compounds,
including more than 60 known carcinogens
formed by incomplete combustion.
–Amongst these are polycyclic aromatic hydrocarbons, –Amongst these are polycyclic aromatic hydrocarbons,
e.g.benzopyrene, nitrosamines, aromatic amines,
aldehydes, and other volatile compounds.
–Metabolism by the body’s P-450 system leads to
further reactive intermediates which can combine
with DNA and cause mutations
–Tobacco smoking also contributes to atherosclerosis
including more than 60 known carcinogens
formed by incomplete combustion.
–Amongst these are polycyclic aromatic hydrocarbons, –Amongst these are polycyclic aromatic hydrocarbons,
e.g.benzopyrene, nitrosamines, aromatic amines,
aldehydes, and other volatile compounds.
–Metabolism by the body’s P-450 system leads to
further reactive intermediates which can combine
with DNA and cause mutations
–Tobacco smoking also contributes to atherosclerosis
IMIDAZOLEALKALOIDS
ImidazoleAlkaloids
•The amino acid L-histidinethe likely
presursore
•Pilocarpusis medicinally important
•The amino acid L-histidinethe likely
presursore
•Pilocarpusis medicinally important
Pilocarpus. Syn: Jabaranda
•Consists of the dried leaflets of
Pilocarpusjaborandi, P.
microphyllus, or P. pennatifolius
(Rutaceae), small shrubs from
Brazil and Paraguay. Brazil and Paraguay.
•Pilocarpusmicrophyllusis
currently the main source.
•Consists of the dried leaflets of
Pilocarpusjaborandi, P.
microphyllus, or P. pennatifolius
(Rutaceae), small shrubs from
Brazil and Paraguay. Brazil and Paraguay.
•Pilocarpusmicrophyllusis
currently the main source.
•Constituent:
–Pilocarpineis the
principal
–Pilocarpineis the
principal
•Use
–Used in eye drops as mioticsand for the
treatment of glaucoma.
•Causing constriction of the pupil and enhancement of •Causing constriction of the pupil and enhancement of
outflow of aqueous humour
•Pilocarpinegives relief for both narrow angle and wide
angle glaucoma
–Used in eye drops as mioticsand for the
treatment of glaucoma.
•Causing constriction of the pupil and enhancement of •Causing constriction of the pupil and enhancement of
outflow of aqueous humour
•Pilocarpinegives relief for both narrow angle and wide
angle glaucoma
–It is antagonistic to atropine
–As muscarinicagonists, pilocarpineand analogues
are also being investigated for potential treatment
of Alzheimer’s diseaseof Alzheimer’s disease
–As muscarinicagonists, pilocarpineand analogues
are also being investigated for potential treatment
of Alzheimer’s diseaseof Alzheimer’s disease
AMINO ALKALOIDS AMINO ALKALOIDS
Amino Alkaloids
•Most of these alkaloids are simple amines and
are simple derivatives of phenylethylamine
•Are also called proto alkaloids
•Most of these alkaloids are simple amines and
are simple derivatives of phenylethylamine
•Are also called proto alkaloids
Ephedra; Ma-hung
•From dried young stems
of Ephedrageradiana
(Ephedraceae)
•From dried young stems
of Ephedrageradiana
(Ephedraceae)
•Constituent:
–(−) Ephedrine is the chief
constent
–(+) pseudoephedrine and
the demethylanalogues the demethylanalogues
(−)-norephedrineand (+)-
norpseudoephedrineare
also present
–(−) Ephedrine is the chief
constent
–(+) pseudoephedrine and
the demethylanalogues the demethylanalogues
(−)-norephedrineand (+)-
norpseudoephedrineare
also present
Use
–Ephedrineis a sympathomimeticamine with
effects similar to noradrenaline
–It has only weak action on adrenoreceptors, but it –It has only weak action on adrenoreceptors, but it
is able to displace noradrenalinefrom storage
vesicles in the nerve terminals
–It is orally active and has a longer duration of
action than noradrenaline
–Ephedrineis a sympathomimeticamine with
effects similar to noradrenaline
–It has only weak action on adrenoreceptors, but it –It has only weak action on adrenoreceptors, but it
is able to displace noradrenalinefrom storage
vesicles in the nerve terminals
–It is orally active and has a longer duration of
action than noradrenaline
•Has bronchodilator activity
–Giving relief in asthma
•A vasoconstrictor action on mucous
membranesmembranes
–making it an effective nasal decongestant
•Pseudoephedrineis also widely used in
compound cough and cold preparations and
as a decongestant
–Giving relief in asthma
•A vasoconstrictor action on mucous
membranesmembranes
–making it an effective nasal decongestant
•Pseudoephedrineis also widely used in
compound cough and cold preparations and
as a decongestant
•The herbal drug ephedrabeing traded as
‘herbal ecstasy’
–Consumption gives CNS stimulation, but in high
amounts can lead to hallucinations, fear, and amounts can lead to hallucinations, fear, and
psychosis.
‘herbal ecstasy’
–Consumption gives CNS stimulation, but in high
amounts can lead to hallucinations, fear, and amounts can lead to hallucinations, fear, and
psychosis.
Khat, Abyssinian tea
•Consists of the fresh
leaves of Catha edulis
(Celastraceae)
•Consists of the fresh
leaves of Catha edulis
(Celastraceae)
•Constituent:
–Dried leaves contain up to 1% cathine((+)-
norpseudoephedrine)
–young fresh leaves contain (−)-cathinoneas the –young fresh leaves contain (−)-cathinoneas the
principal
–Dried leaves contain up to 1% cathine((+)-
norpseudoephedrine)
–young fresh leaves contain (−)-cathinoneas the –young fresh leaves contain (−)-cathinoneas the
principal
•Pharmacologic action/use:
–Cathinonehas similar pharmacological properties
as the synthetic CNS stimulant (+)-
amfetamine/dexamfetaminewith a similar amfetamine/dexamfetaminewith a similar
potency
–Both compounds act by inducing release of
catecholamines
–Cathinonehas similar pharmacological properties
as the synthetic CNS stimulant (+)-
amfetamine/dexamfetaminewith a similar amfetamine/dexamfetaminewith a similar
potency
–Both compounds act by inducing release of
catecholamines
(−)-Cathinone
(+)-Amfetamine
(+)-Amfetamine
•The traditional use alleviates hunger and
fatigue, but also gives a sensation of general
well-being
–Users become cheerful and talkative, and khathas
become a social drug
Users become cheerful and talkative, and khathas
become a social drug
•Prolonged usage can lead to hypertension,
insomnia, or even mania
•Khatconsumption may lead to psychological
dependence
fatigue, but also gives a sensation of general
well-being
–Users become cheerful and talkative, and khathas
become a social drug
Users become cheerful and talkative, and khathas
become a social drug
•Prolonged usage can lead to hypertension,
insomnia, or even mania
•Khatconsumption may lead to psychological
dependence
Colchicum; Autumn crocus
•It consists of the dried
unripe seeds of
Culchicumautumnale
(Liliaceae)
•It is a native of Europe, •It is a native of Europe,
is widely cultivated as
an ornamental garden
plant, and is grown for
drug use, mainly in
Europe and North
Africa.
•It consists of the dried
unripe seeds of
Culchicumautumnale
(Liliaceae)
•It is a native of Europe, •It is a native of Europe,
is widely cultivated as
an ornamental garden
plant, and is grown for
drug use, mainly in
Europe and North
Africa.
•Chemsicalconstituents:
–colchicines (derived from
tyrosine) is the principal
–colchicines (derived from
tyrosine) is the principal
•Use
–Extracts and the active colchicine, have been used
in the treatment of gout
–Colchicineis an effective treatment for acute
attacks, but it is very toxic, and this restricts its
general usegeneral use
–Colchicines is widely used to produce poly ploidy
(increase in number of chromosome)
–Extracts and the active colchicine, have been used
in the treatment of gout
–Colchicineis an effective treatment for acute
attacks, but it is very toxic, and this restricts its
general usegeneral use
–Colchicines is widely used to produce poly ploidy
(increase in number of chromosome)
Pseudo Alkaloids
STEROIDAL ALKALOIDSSTEROIDAL ALKALOIDS
•Many plants in the Solanaceaeaccumulate
steroidal alkaloids based on a C
27cholestane
skeleton
steroidal alkaloids based on a C
27cholestane
skeleton
Kurchior holarrhenabark
•It is obtained from the
stem bark of
Holarrhena
antidysenterica
(Apocynaceae)(Apocynaceae)
•It is obtained from the
stem bark of
Holarrhena
antidysenterica
(Apocynaceae)(Apocynaceae)
•Constituents:
–Kurchicontains numerous
steroidal type alkaloids (1.8
4.5%) including conessine, 4.5%) including conessine,
norconessine, isoconessine
and kurchine
–Kurchicontains numerous
steroidal type alkaloids (1.8
4.5%) including conessine, 4.5%) including conessine,
norconessine, isoconessine
and kurchine
•Use
–Kurchiis anti-protozoalin activity and used in the
treatment of amoebic dysentery.
–A traditional preparation of kurchibark is –A traditional preparation of kurchibark is
commonly used for chronic amoebiasis
–Kurchiis anti-protozoalin activity and used in the
treatment of amoebic dysentery.
–A traditional preparation of kurchibark is –A traditional preparation of kurchibark is
commonly used for chronic amoebiasis
TERPENOIDALKALOIDS
•A variety of alkaloids based on mono-, sesqui-,
di-, and tri-terpenoidskeletons have been
characterized,
–Aconite (Aconitum species; Ranunculaceae) and –Aconite (Aconitum species; Ranunculaceae) and
species of Delphinium (Ranunculaceae). Plants of
both genera owe their highly toxic nature to
diterpenoidalkaloids.
di-, and tri-terpenoidskeletons have been
characterized,
–Aconite (Aconitum species; Ranunculaceae) and –Aconite (Aconitum species; Ranunculaceae) and
species of Delphinium (Ranunculaceae). Plants of
both genera owe their highly toxic nature to
diterpenoidalkaloids.
Aconite
•Are species of Aconitum
(Ranunculaceae),
•Their alkaloid content, mainly
in the roots, makes them in the roots, makes them
some of the most toxic plants
commonly encountered.
•Are species of Aconitum
(Ranunculaceae),
•Their alkaloid content, mainly
in the roots, makes them in the roots, makes them
some of the most toxic plants
commonly encountered.
•The toxic alkaloids (0.3–
1.5%) are complex
diterpene-derived
esters.
•Aconitineis the
principal component
(about 30%) and is a
diesterof aconinewith
acetic and benzoic
acids.
1.5%) are complex
diterpene-derived
esters.
•Aconitineis the
principal component
(about 30%) and is a
diesterof aconinewith
acetic and benzoic
acids.
•Hydrolysis products benzoylaconineand aconineare also
present in dried plant material.
•These alkaloids appear to behave as neurotoxins by acting on
sodium channels.
•All species of Aconitum and Delphinium are potentially toxic •All species of Aconitum and Delphinium are potentially toxic
to man and animals and must be treated with caution.
present in dried plant material.
•These alkaloids appear to behave as neurotoxins by acting on
sodium channels.
•All species of Aconitum and Delphinium are potentially toxic •All species of Aconitum and Delphinium are potentially toxic
to man and animals and must be treated with caution.
•The dried roots of Aconitumnapelluswere
used, mainly externally for relief of pain,
–e.g. in rheumatism.
•Aconite is a very potent and quick-acting •Aconite is a very potent and quick-acting
poison which is now rarely used internally
except in homeopathic doses
•It was formerly used for the preparation of an
antineuralgicliniment
used, mainly externally for relief of pain,
–e.g. in rheumatism.
•Aconite is a very potent and quick-acting •Aconite is a very potent and quick-acting
poison which is now rarely used internally
except in homeopathic doses
•It was formerly used for the preparation of an
antineuralgicliniment
PURINEALKALOIDS PURINEALKALOIDS
•Purinealkaloids'constitutesecondary
metabolites and are derivatives of xanthine.
•Three well-known examples are cafieine,
theophylline, and theobromine. theophylline, and theobromine.
•Beverages such as tea and coffee owe their
stimulant properties to these substances.
metabolites and are derivatives of xanthine.
•Three well-known examples are cafieine,
theophylline, and theobromine. theophylline, and theobromine.
•Beverages such as tea and coffee owe their
stimulant properties to these substances.
Caffeine, Theobromine, Theophylline
•all methyl derivatives of xanthineand they
commonly co-occur in a particular plant.
•The major sources of these compounds are
the beverage materials such as tea, coffee, the beverage materials such as tea, coffee,
cocoa, and cola, which owe their stimulant
properties to these water-soluble alkaloids.
•all methyl derivatives of xanthineand they
commonly co-occur in a particular plant.
•The major sources of these compounds are
the beverage materials such as tea, coffee, the beverage materials such as tea, coffee,
cocoa, and cola, which owe their stimulant
properties to these water-soluble alkaloids.
•competitively inhibit phosphodiesterase,
resulting in an increase in cyclic AMP and
subsequent release of adrenaline.
•This leads to a stimulation of the CNS, a relaxation of •This leads to a stimulation of the CNS, a relaxation of
bronchial smooth muscle, and induction of diuresis, as
major effects.
•These effects vary in the three compounds.
resulting in an increase in cyclic AMP and
subsequent release of adrenaline.
•This leads to a stimulation of the CNS, a relaxation of •This leads to a stimulation of the CNS, a relaxation of
bronchial smooth muscle, and induction of diuresis, as
major effects.
•These effects vary in the three compounds.
•Caffeineis the best CNS stimulant, and has
weak diuretic action.
–Caffeine stimulates the central nervous system
and has a weak diuretic action. Whereas and has a weak diuretic action. Whereas
theobromineacts in the reverse.
•Caffeine is used medicinally as a CNS stimulant, usually
combined with another therapeutic agent, as in
compound analgesic preparations.
weak diuretic action.
–Caffeine stimulates the central nervous system
and has a weak diuretic action. Whereas and has a weak diuretic action. Whereas
theobromineacts in the reverse.
•Caffeine is used medicinally as a CNS stimulant, usually
combined with another therapeutic agent, as in
compound analgesic preparations.
•Theobrominehas little stimulant action, but
has more diuretic activity and also muscle
relaxant properties.
•Theophyllinealso has low stimulant action •Theophyllinealso has low stimulant action
and is an effective diuretic, but it relaxes
smooth muscle better than caffeine or
theobromine.
has more diuretic activity and also muscle
relaxant properties.
•Theophyllinealso has low stimulant action •Theophyllinealso has low stimulant action
and is an effective diuretic, but it relaxes
smooth muscle better than caffeine or
theobromine.
•Theobromineis of value as a diuretic and
smooth muscle relaxant, but is not now
routinely used.
smooth muscle relaxant, but is not now
routinely used.
•Theophyllineis an important smooth muscle
relaxant for relief of bronchospasm, and is
frequently dispensed in slow release
formulations to reduce side-effects. formulations to reduce side-effects.
–It is also available as aminophylline(a more
soluble preparation containing theophyllinewith
ethylenediamine) and cholinetheophyllinate
(theophyllineand choline).
relaxant for relief of bronchospasm, and is
frequently dispensed in slow release
formulations to reduce side-effects. formulations to reduce side-effects.
–It is also available as aminophylline(a more
soluble preparation containing theophyllinewith
ethylenediamine) and cholinetheophyllinate
(theophyllineand choline).
MISCELLANEOUS ALKALOIDS MISCELLANEOUS ALKALOIDS
IndolizidineAlkaloids
•characterized by fused six-and five-
memberedrings, with a nitrogen atom at the
ring fusion
•Derived from lysine •Derived from lysine
•characterized by fused six-and five-
memberedrings, with a nitrogen atom at the
ring fusion
•Derived from lysine •Derived from lysine
•Polyhydroxy-indolizidinessuch as
–swainsoninefrom Swainsona
canescens(Fabaceae) and
–castanosperminefrom the Moreton
Bay chestnut Castanospermum
austral(Fabaceae)
Bay chestnut Castanospermum
austral(Fabaceae)
•have demonstrated activity against
the AIDS virus HIV, by their ability to
inhibit glycosidase enzymes involved
in glycoprotein biosynthesis.
–swainsoninefrom Swainsona
canescens(Fabaceae) and
–castanosperminefrom the Moreton
Bay chestnut Castanospermum
austral(Fabaceae)
Bay chestnut Castanospermum
austral(Fabaceae)
•have demonstrated activity against
the AIDS virus HIV, by their ability to
inhibit glycosidase enzymes involved
in glycoprotein biosynthesis.
QuinolizidineAlkaloids
•bicyclic ring system,
formed from two
molecules of lysine.
•bicyclic ring system,
formed from two
molecules of lysine.
•Mainly found in plants of Fabaceaefamily
–They deter or repel feeding of herbivores, and are
toxic to them by a variety of mechanisms
–They deter or repel feeding of herbivores, and are
toxic to them by a variety of mechanisms
•A number of plants (Laburnum, Cytisus,
Lupinus) containing significant quantities of
these alkaloids:
–Potentially toxic to humans, and are known to be –Potentially toxic to humans, and are known to be
responsible for human poisoning
Lupinus) containing significant quantities of
these alkaloids:
–Potentially toxic to humans, and are known to be –Potentially toxic to humans, and are known to be
responsible for human poisoning
PyrrolizidineAlkaloids
•Two molecules of ornithineare utilized in
formation of the bicyclic pyrrolizidineskeleton
•Two molecules of ornithineare utilized in
formation of the bicyclic pyrrolizidineskeleton
PyrrolizidineAlkaloids
•Pyrrolizidinealkaloids have a wide
distribution, but are characteristic of certain
genera of the
–Boraginaceae(e.g. Heliotropium, Cynoglossum, –Boraginaceae(e.g. Heliotropium, Cynoglossum,
and Symphytum),
–the Asteraceae(e.g. Senecio) and
–the Fabaceae(e.g. Crotalaria)
•Pyrrolizidinealkaloids have a wide
distribution, but are characteristic of certain
genera of the
–Boraginaceae(e.g. Heliotropium, Cynoglossum, –Boraginaceae(e.g. Heliotropium, Cynoglossum,
and Symphytum),
–the Asteraceae(e.g. Senecio) and
–the Fabaceae(e.g. Crotalaria)
•Pyrrolizidinebases rarely occur in the free
form, but are generally found as esters with
rare mono-or di-basic acids, the necicacids
form, but are generally found as esters with
rare mono-or di-basic acids, the necicacids
•Senecioninefrom
Seneciospecies is a
diesterof retronecine
with senecicacid.
Seneciospecies is a
diesterof retronecine
with senecicacid.
•Many pyrrolizidinealkaloids are known to
produce pronounced hepatic toxicityand
there are many recorded cases of livestock
poisoningpoisoning
•Potentially toxic structures have 1, 2-
unsaturation in the pyrrolizidinering and an
ester function on the side-chain.
produce pronounced hepatic toxicityand
there are many recorded cases of livestock
poisoningpoisoning
•Potentially toxic structures have 1, 2-
unsaturation in the pyrrolizidinering and an
ester function on the side-chain.
•These alkaloids are
transformed by mammalian
liver oxidasesinto reactive
pyrrolestructurespyrrolestructures
–potent alkylatingagents and
react with suitable cell
nucleophiles,
•e.g. nucleic acids and
proteins.
transformed by mammalian
liver oxidasesinto reactive
pyrrolestructurespyrrolestructures
–potent alkylatingagents and
react with suitable cell
nucleophiles,
•e.g. nucleic acids and
proteins.
Conium maculatum
•Conium maculatum
(Apiaceae) or poison
hemlock is a large
biennial herb indigenous
to Europe and naturalized
in North and South
to Europe and naturalized
in North and South
America.
•The dried unripe fruits
were formerly used as a
pain reliever and
sedative, but have no
medicinal use now
•Conium maculatum
(Apiaceae) or poison
hemlock is a large
biennial herb indigenous
to Europe and naturalized
in North and South
to Europe and naturalized
in North and South
America.
•The dried unripe fruits
were formerly used as a
pain reliever and
sedative, but have no
medicinal use now
•The ancient Greeks are said to have executed
condemned prisoners, including Socrates,
using poison hemlock.
–The poison causes gradual muscular paralysis –The poison causes gradual muscular paralysis
followed by convulsions and death from
respiratory paralysis
condemned prisoners, including Socrates,
using poison hemlock.
–The poison causes gradual muscular paralysis –The poison causes gradual muscular paralysis
followed by convulsions and death from
respiratory paralysis
•The major alkaloid (about 90%) is the volatile
liquid coniine
–acetate derived
liquid coniine
–acetate derived
belongs to amino alkaloids?
A. CathenoneB. Connesine
C. Cocaine D. Theobromine
A. CathenoneB. Connesine
C. Cocaine D. Theobromine
alkaloid derived from ornithine
A. Reserpine B. Morphine
C. HyoscyamineD. Quinine
drug containing Pseudo alkaloids? drug containing Pseudo alkaloids?
A. Holarhenabark B. Ephedraherb
C. Ergot D. Senociospecies
A. Reserpine B. Morphine
C. HyoscyamineD. Quinine
drug containing Pseudo alkaloids? drug containing Pseudo alkaloids?
A. Holarhenabark B. Ephedraherb
C. Ergot D. Senociospecies
Categorize the ff accordingly
•Categorize them under true, proto and pseudo
alkaloids
•which one are tryptophanederived
•Which one are obtained from Apocynaceae
–a.Ergotamine h.Physostigmine
–b.Atropine i.Lobeline
–c.Morphine j.cathinone–c.Morphine j.cathinone
–d.Cocaine k. Aconitine
–e.Vincristine l.Theophylline
–f.Quinine m.Swainsonine
–g.Reserpine n.Ephedrine
True—a,b,c,d,e,f,g,h,I,mProto-j,-n Pseudo-k,l
Trypthohanderived: a,e,g,f,h
Ornithinederived: b,d,
Apocynaceae: e, g
•Categorize them under true, proto and pseudo
alkaloids
•which one are tryptophanederived
•Which one are obtained from Apocynaceae
–a.Ergotamine h.Physostigmine
–b.Atropine i.Lobeline
–c.Morphine j.cathinone–c.Morphine j.cathinone
–d.Cocaine k. Aconitine
–e.Vincristine l.Theophylline
–f.Quinine m.Swainsonine
–g.Reserpine n.Ephedrine
True—a,b,c,d,e,f,g,h,I,mProto-j,-n Pseudo-k,l
Trypthohanderived: a,e,g,f,h
Ornithinederived: b,d,
Apocynaceae: e, g
•Categorize them under true, proto and pseudo
alkaloids
•which one are tryptophanederived
•Which one are obtained from Apocynaceae•Which one are obtained from Apocynaceae
alkaloids
•which one are tryptophanederived
•Which one are obtained from Apocynaceae•Which one are obtained from Apocynaceae
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