ALKALOIDS Flashcards
Are extremely difficult to define for they do not represent a homogenous group of
compounds either from the chemical,
biochemical or physiologic point of view.
ALKALOIDS
Naturally occurring chemical compounds
containing basic nitrogen atoms.
ALKALOIDS
Commonly applied to basic nitrogenous
compounds of plant origin that is
physiologically active.
ALKALOIDS
Usually classified according to the nature of the basic chemical structures from which they are derived.
ALKALOIDS
All do occur in plants which have been the
rich sources.
ALKALOIDS
Some are found in animals and practically all have been reproduced by chemical synthesis.
ALKALOIDS
Examples of Alkaloids:
BACTERIA
FUNGI
FROGS
INSECTS
Usually a bitter taste.
ALKALOIDS
By agreement, chemical rules designate
that the name of alkaloids should end in
INE.
ALKALOIDS
By agreement, chemical rules designate
that the name of alkaloids should end in
____.
INE
The term Alkaloid (______) is commonly
used to designate basic heterocyclic
nitrogenous compounds of plant origin that are physiologically active.
ALKALI-LIKE
Some alkaloids are not basic.
BASICITY
Examples or Basicity:
COLCHICINE, PIPERINE, QUATERNARY ALKALOIDS
The nitrogen in some alkaloids is
not a heterocyclic ring.
NITROGEN
Examples of Nitrogen:
COLCHICINE, EPHEDRINE, MESCALINE
Derived from amino acids and have nitrogen in a heterocyclic ring. – Atropine
TRUE/TYPICAL ALKALOIDS
Derived from amino acids and do not have nitrogen in a heterocyclic ring.
– Ephedrine
PROTO-ALKALOIDS
Not derived from amino acids but have nitrogen in a heterocyclic ring. - Caffeine
PSEUDO-ALKALOIDS
Non-alkaloids that gives false positive reaction with alkaloidal reagents.
FALSE ALKALOIDS
Types of Alkaloids:
TRUE/TYPICAL ALCALOIDS
PROT-ALKALOIDS
PSEUDO-ALKALOIDS
FALSE ALKALOIDS
Example of true/typical alcaloid
ATROPINE
Example or Proto-Alkaloids
EPHEDRINE
Example of Pseudo-Alkaloids
CAFFEINE
Are cyclic organic compounds
containing nitrogen in negative state of
oxidation with limited distribution
among living organisms.
ALKALOIDS
Occurrence of Alkaloids:
• RARE IN LOWER PLANTS
• DICOTS ARE MORE RICH IN ALKALOIDS THAN MONOCOTS
• MONOCOT PLANTS WITH ALKALOIDS
• FAMILIES FREE FROM ALKALOIDS
Monocot plants with Alkaloids:
AMARYLLIDACEAE
LILIACEAE
Families free from Alkaloids:
ROSACEAE
LABIATAE
Families rich in Alkaloids:
• APOCYNACEAE
• SOLANACEAE
• PAPAVERACEAE
• RUBIACEAE
• RANUNCULACEAE
• BERBERIDACEAE
Poisonous agent protecting the plant against insects and hervibores due to its bitterness and toxicity.
ALKALOIDS
End product of detoxification reaction
representing a metabolic locking-up of
compounds otherwise harmful to the plants– waste products.
ALKALOIDS
As regulatory growth factor in certain
metabolic systems.
ALKALOIDS
Reserved the substance capable of supplying nitrogen or other necessary elements to the plant’s economy– Sources of nitrogen in case of nitrogen deficiency.
ALKALOIDS
Utilized as source of energy in case of
deficiency in carbon dioxide assimilation.
ALKALOIDS
Plant part used in Datura
ALL PARTS
Plant part used in Tobacco
LEAVES
Plant part used in Cinchona
BARKS
Plant part used in Belladonna, Aconite
ROOTS
Plant part used in Black Pepper
FRUITS
Plant part used in Areca, Nux Vomica, Physostigma
SEEDS
Plant part used in Ipecac, Hydrastis
RHIZOMES AND ROOTS
Plant part used in Opium
LATEX
Plant part used in Ergot
FUNGI
From the Generic Name of the plant
yielding them:
ATROPINE - ATROPA
HYDRASTINE - HYDRASTIS
From the Specific Name of the plant
yielding them:
COCAINE - COCA
BELLADONINE - BELLADONNA
Atropa
ATROPINE
HYDRASTIS
HYDRASTINE
COCA
COCAINE
Belladonna
BELLADONINE
From the Common Name of the plant
yielding them.
ERGOTAMINE - ERGOT
Ergot
ERGOTAMINE
From their Physiologic Activity
EMETINE
MORPHINE
Occasionally, from the Discoverer
PELLETIERINE - PELLETIER
Pelletier
PELLETIERINE
Sometimes, a prefix or suffix is added to
the name of a principal alkaloid to
designate another alkaloid from the
same source.
▪ Quinine
▪ Quinidine
▪ Hydroquinidine
Forms of Alkaloids:
• FREE BASES
• SALTS WITH ORGANIC ACIDS
• SALTS WITH INORGANIC ACIDS
• SALTS WITH SPECIAL ACIDS
• GLYCOSIDAL FORM
Examples of Salt with Organic Acids
OXALIC ACID, ACETIC ACID
Examples of Salts with Inorganic Acid:
HYDROCHLORIC ACID, SULFURIC ACID
Examples of Salts with Special Acids:
MECONIC ACID - OPIUM
QUINIC ACID - CINCHONA
Examples of Glycosidal Form
SOLANINE - SOLANUM
Insoluble or sparingly soluble in water.
ALKALOIDS
freely soluble in water.
SALTS WITH ACIDS
soluble in alcohol, ether, chloroform or other relatively nonpolar, immiscible solvents.
FREE ALKALOIDS
( However, alkaloidal salts are insoluble. )
( Most are crystalline solids– often a useful
means of microscopic identification. )
Few are amorphous
ALKALOIDS
( Form double-salts with compounds of
Mercury (Hg), Gold (Au), Platinum (Pt),
and other heavy metals. )
The _______ are usually obtained as
precipitates and many of them are
microcrystallographically
characteristics.
DOUBLE SALTS
Few are Amorphous solids
EMETINE
Some of the alkaloids are liquids that are either:
VOLATILE - NICOTINE and CONIINE
NON-VOLATILE - PILOCARPINE AND AND HYOSCINE
End product of detoxification reaction
representing a metabolic locking-up of
compounds otherwise harmful to the plants
WASTE PRODUCT
Non-volatile
PILOCARPINE and HYOSCINE
Color of Colchicine and Berberine
YELLOW
Color of Canadine
ORANGE
Color of Salts of Sanguinarine
Copper Red
Examples of Yellow Color
COLCHICINE and BERBERINE
Examples of Orange Color:
CANADINE
Examples of Copper Red:
SALTS OF SANGUINARINE
❑Both alkaloidal bases and their salts are
soluble in alcohol.
❑Generally, the bases are soluble in organic solvents and insoluble in water
SOLUBILITY
BASES INSOLUBLE IN ORGANIC SOLVENTS
• MORPHINE IN ETHER
• THEOBROMINE IN BENZENE
• THEOPHYLLINE IN BENZENE
BASES SOLUBLE IN WATER
• CAFFEINE
• CODEINE
• COLCHICINE
• EPHEDRINE
• PILOCARPINE
• QUATERNARY AMMONIUM BASES
are usually soluble in water and
insoluble or sparingly soluble in organic
solvents.
SALTS
Exception of the Physical Properties of Alkaloids
• SALTS INSOLUBLE IN WATER
• SALTS SOLUBLE IN IN ORGANIC SOLVENTS
Salts insoluble in water
QUININE MONOSULPHATE
Salts soluble in organic solvents
LOBELINE AND APOATROPINE HCL-CHLOROFORM