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ALKALOIDS
CLASSIFICATION,PHYSICAL AND CHEMICAL PROPERTIES,CHEMISTRY
ORGIN , HISTORY AND INTRODUCTION
• THE TERM “ALKALOID” [ALKALI-LIKE] IS COMMONLY USED TO DESIGNATE BASIC HETEROCYCLIC
NITROGENOUS COMPOUNDS OF PLANT ORGIN THAT ARE PHYSIOLOGICALLY ACTIVE
• The term alkaloid of pflanzenlkalien was coined by Meissner a German Pharmacist in 1819
• The mankind has been using alkaloid for various purposes like poisons, medicines, teas etc.
• The French scientist Derosne in 1803 isolated Narcotine
DISTRIBUTION IN PLANTS
1. LEAVES: TOBACCO
2. LATEX : OPIUM
3. FRUIT : BLACK PEPPER
4. ALL PARTS: DATURA
DISTRIBUTION AND OCCURANCE
• Rare in lower plants
• Dicots are more rich in alkaloids than monocots
• Families rich in alkaloids : APOCYNACEAE,RUBIACEAE,SOLANACEAE AND PAPAVERACEAE
FUNCTION IN PLANTS
• They may act as protective against insects and herbivorous due to their bitterness
and toxicity.
• Act as source of nitrogen in the case of nitrogen deficiency.
• They sometimes act as growth regulators in certain metabolic system.
• They may be utilised as a source of energy in the case of deficiency in carbon
dioxide assimilation.
• In certain cases they are final products of detoxification.
EFFECT OF ALAKLOID IN HUMANS
• High biological activity
• Produce varying degree of physiological and psychological responses.
• Largely interfering with neurotransmitters.
• In large dose-highly toxic or fatal
• In small dose –many have therapeutic value eg.painkillers
STIMULANTS HALLUCINOGENS
TROPANEALKALOIDS
MESCALNE
LSD
DEPPRESENTS
MORPHIN
CODEINE
HEROINE
COCAINE
EPHEDRINE
CAFFEINE
PSYCHOACTIVE ALKALOIDS
CLASSIFICATIONS
A. TRUE (TYPICAL) ALKALOIDS that are derived from amino acids and have nitrogen
in a heterocyclic ring eg. Atropine
B. PROTOALKALOIDS that are derived from amino acids and do not have nitrogen in
a heterocyclic ring eg. Ephrdrine
C. PSUEDOALKALOIDS that are not derived from amino acid but have nitrogen in a
heterocyclic ring eg. Caffeine
D. FALSE ALKALOIDS are non alkaloids give false positive reaction with alkaloidal
reagents.
PHYSICAL PROPERTIES
• COLOURLESS
• CRYSTALLINE SOLIDS
• INSOLUBLE IN WATER
• SOLUBLE IN ORGANIC SOLVENTS
• TASTE : BITTER
• OPTICALLY ACTIVE (MOSTLY LEAVO ROTATORY)
CONDITION
• Most alkaloids are crystalline
solids.
• Few alkaloids are amorphous
solids eg. Emetine
• Some are liquids that are
either (A) VOLTILE eg. Nicotine
and coniine (B) NONVOLATILE
eg.pilocarpine and hyoscine
COLOUR
• The majority of alkaloids are
colourless
• EXEPTIONS : Colchicine and
Berberine are yellow
Canadine is orange
SOLUBILITY
• Both alkaloidal bases and their salts are soluble in alcohol
• Generally the bases are soluble in organic solvents and insoluble in
water.
• Exceptions:
Bases soluble in water : caffeine ,ephedrine ,codeine
Bases insoluble or sparingly soluble in certain organic solvents : morphine
in ether
• Salts are usually soluble in water and insoluble or sparingly soluble in
organic solvents
• Exceptions:
Salt insoluble in water – quinine monosulphate
Salts soluble in organic solvents – iobeline and apotropine hydrochlorides
are soluble in chloroform.
CHEMICAL PROPERTIES
• In addition to carbon ,nitrogen, and hydrogen most alkaloids contains oxygen in their molecules.
• Few alkaloids are oxygen free such as nicotine and coniine.
• Due to their basic character alkaloids with acids make salts.
• Strong bases form salts with very weak acids.
• Weak bases require strong acids
• Very weak bases form unstable salts.
• Amphoteric alkaloids can form salts with both acids and alkalies
• Alkaloids showing acidic character do not form salts with acids eg. rianine
CHEMICAL TEST
1. WAGNERS TEST : REDDISH BROWN PERCIPITATE
2. MAYERS TEST: CREAMY PERCIPITATE WITH
TRUEALKALOIDS
3. HAGGERS TEST:YELLOW PERCIPITATE WITH
TRUEALKALOIDS
4. DRAGENDOFF TEST : REDDISH BROWN PERCIPITATE
.
• CHEMICAL CHARECTORS
THE UNSHARED ELECTRON PAIR ON THE NITROGEN
ATOM IS RESPONSIBLE FOR ALKALOID BASICITY
SOME ALJKALOIDS LOSE WATER MOLECULES TO
FORM THE ANHYDRO-OR APOALKALOIDS EG.
MORPHINE AND APOMORPHINE
N OR O DEMETHYLATIONS OF CERTAIN ALAKLOIDS
CAN TAKE PLACE UPON HEATING WITH MINERAL
ACIDS EG. QUININE , NARCOTINE
• EFFECT OF HEAT AND ACID ON
ALKALOID STABILITY
• HEAT: ALAKALOIDS GENERALLY DECOMPOSE ON
HEATING WHILE SOME OF THEM SUBLIME
EG.CAFFINE
• ACID: COLD CONCENTRATED ACID MAY CAUSE
DRAMATIC CHANGES IN ALKALOIDS
THANK YOU
LAKSHMI MANOJ

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ALKALOIDS.pptx

  • 2. ORGIN , HISTORY AND INTRODUCTION • THE TERM “ALKALOID” [ALKALI-LIKE] IS COMMONLY USED TO DESIGNATE BASIC HETEROCYCLIC NITROGENOUS COMPOUNDS OF PLANT ORGIN THAT ARE PHYSIOLOGICALLY ACTIVE • The term alkaloid of pflanzenlkalien was coined by Meissner a German Pharmacist in 1819 • The mankind has been using alkaloid for various purposes like poisons, medicines, teas etc. • The French scientist Derosne in 1803 isolated Narcotine
  • 3. DISTRIBUTION IN PLANTS 1. LEAVES: TOBACCO 2. LATEX : OPIUM 3. FRUIT : BLACK PEPPER 4. ALL PARTS: DATURA
  • 4. DISTRIBUTION AND OCCURANCE • Rare in lower plants • Dicots are more rich in alkaloids than monocots • Families rich in alkaloids : APOCYNACEAE,RUBIACEAE,SOLANACEAE AND PAPAVERACEAE
  • 5. FUNCTION IN PLANTS • They may act as protective against insects and herbivorous due to their bitterness and toxicity. • Act as source of nitrogen in the case of nitrogen deficiency. • They sometimes act as growth regulators in certain metabolic system. • They may be utilised as a source of energy in the case of deficiency in carbon dioxide assimilation. • In certain cases they are final products of detoxification.
  • 6. EFFECT OF ALAKLOID IN HUMANS • High biological activity • Produce varying degree of physiological and psychological responses. • Largely interfering with neurotransmitters. • In large dose-highly toxic or fatal • In small dose –many have therapeutic value eg.painkillers
  • 8. CLASSIFICATIONS A. TRUE (TYPICAL) ALKALOIDS that are derived from amino acids and have nitrogen in a heterocyclic ring eg. Atropine B. PROTOALKALOIDS that are derived from amino acids and do not have nitrogen in a heterocyclic ring eg. Ephrdrine C. PSUEDOALKALOIDS that are not derived from amino acid but have nitrogen in a heterocyclic ring eg. Caffeine D. FALSE ALKALOIDS are non alkaloids give false positive reaction with alkaloidal reagents.
  • 9. PHYSICAL PROPERTIES • COLOURLESS • CRYSTALLINE SOLIDS • INSOLUBLE IN WATER • SOLUBLE IN ORGANIC SOLVENTS • TASTE : BITTER • OPTICALLY ACTIVE (MOSTLY LEAVO ROTATORY)
  • 10. CONDITION • Most alkaloids are crystalline solids. • Few alkaloids are amorphous solids eg. Emetine • Some are liquids that are either (A) VOLTILE eg. Nicotine and coniine (B) NONVOLATILE eg.pilocarpine and hyoscine COLOUR • The majority of alkaloids are colourless • EXEPTIONS : Colchicine and Berberine are yellow Canadine is orange SOLUBILITY • Both alkaloidal bases and their salts are soluble in alcohol • Generally the bases are soluble in organic solvents and insoluble in water. • Exceptions: Bases soluble in water : caffeine ,ephedrine ,codeine Bases insoluble or sparingly soluble in certain organic solvents : morphine in ether • Salts are usually soluble in water and insoluble or sparingly soluble in organic solvents • Exceptions: Salt insoluble in water – quinine monosulphate Salts soluble in organic solvents – iobeline and apotropine hydrochlorides are soluble in chloroform.
  • 11. CHEMICAL PROPERTIES • In addition to carbon ,nitrogen, and hydrogen most alkaloids contains oxygen in their molecules. • Few alkaloids are oxygen free such as nicotine and coniine. • Due to their basic character alkaloids with acids make salts. • Strong bases form salts with very weak acids. • Weak bases require strong acids • Very weak bases form unstable salts. • Amphoteric alkaloids can form salts with both acids and alkalies • Alkaloids showing acidic character do not form salts with acids eg. rianine
  • 12. CHEMICAL TEST 1. WAGNERS TEST : REDDISH BROWN PERCIPITATE 2. MAYERS TEST: CREAMY PERCIPITATE WITH TRUEALKALOIDS 3. HAGGERS TEST:YELLOW PERCIPITATE WITH TRUEALKALOIDS 4. DRAGENDOFF TEST : REDDISH BROWN PERCIPITATE
  • 13. . • CHEMICAL CHARECTORS THE UNSHARED ELECTRON PAIR ON THE NITROGEN ATOM IS RESPONSIBLE FOR ALKALOID BASICITY SOME ALJKALOIDS LOSE WATER MOLECULES TO FORM THE ANHYDRO-OR APOALKALOIDS EG. MORPHINE AND APOMORPHINE N OR O DEMETHYLATIONS OF CERTAIN ALAKLOIDS CAN TAKE PLACE UPON HEATING WITH MINERAL ACIDS EG. QUININE , NARCOTINE • EFFECT OF HEAT AND ACID ON ALKALOID STABILITY • HEAT: ALAKALOIDS GENERALLY DECOMPOSE ON HEATING WHILE SOME OF THEM SUBLIME EG.CAFFINE • ACID: COLD CONCENTRATED ACID MAY CAUSE DRAMATIC CHANGES IN ALKALOIDS
  • 14.
  • 15.
  • 16.