Dr. Md. Rageeb Md.

Usman
Associate Professor
Department of Pharmacognosy

Smt. Sharadchandrika Suresh Patil

College of Pharmacy,
Chopda, Maharashtra, India
 Pseudoalkaloids include steroidal, terpenoid alkaloids & purines.Eg:conessine
& caffeine.

DISTIBUTION :
Alkaloids are widely distributed in higher plants. Eg Apocynaceae,Papaveraceae,
Solanaceae. They are present as salts of organic acids like acetic ,oxalic,
malic, lactic, tartaric, tannic, aconitic acid & few with sugars like
solanum,veratrum.Alkaloids are obtained from leaves (nicotine), bark
(chinchonine,quinine), seeds (strychnine), roots (rauwolfinine,
punarnavine).

PHYSICAL PROPERTIES:
1) Colourless, crystalline solids with sharp melting point.
2) They are amorphous gums or volatile liq.(like coniine, sparteine,
nicotine),some are coloured (betanidin – red, berberine – yellow )
3) Salts are soluble in water, free bases in non polar organic,immiscible
solvents . Salts of free bases are sparingly soluble in organic solvents.
 4) Quaternary bases are only water soluble. Some pseudo &
proto alkaloids show higher solubility in water.
CHEMICAL PROPERTIES :
1) Basicity of alkaloids is due to lone pair of electron on nitrogen.
2) Basicity increases if adjacent functional gr. is electron
releasing.
3) Basicity decreases if adjacent functional gr. is electron
withdrawing.
NOMENCLATURE
They are named
1) Acc/- to family : eg : papavarine, punarnavine.
2) Acc/- to physiological response ; eg : morphine – God of
dreams, emetine –vomit.
3) Acc/- to discoverer: eg: pelletierine – Scientist P.J. Pelletier.
4) Acc/- to prefixes :eg :epi,iso,neo,pseudo.
 Biosynthesis of alkaloids
1) Derived from ornithine : eg : nicotine, hygrine, tropine,cocaine,
hyoscyamine, scopolamine.
2) Derived from lysine ; eg: lupinine , anabasine, lysine,
isopelletierine.
3) Derived from phenylalanine, tyrosine & related aminoacids : eg:
phenylalanine :- ephedrine, mesaline , tyrosine :- papaverine,
morphine, dihydroxyphenylalanine :- emetine, colchicine.
4) Derived from tryptophan :- eg: indole alkaloids like reserpine, ergot.

FUNCTIONS:
1) As reservoir of nitrogen.
2) As reservoir of protein synthesis.
3) As detoxicating agent.
 CLASSIFICATION :
1) Taxonomical : acc/- to family. Eg: solanaceous
2) Pharmacological : acc/- to actions. Eg: analgesic, cardioactive.
3) Biosynthesis : acc/- to precursors used by plants to synthesize complex structure.
4) Chemical : Non heterocyclic : ephedrine
: Heterocyclic : true alkaloids
1) Pyrrole & pyrrolidine : hygrine, coca.
2) Pyridine & piperidine : arecoline, anabasine. Coniine, lobeline, pelletierine,
trigonelline.
3) Pyrrolizidine : echimidine.
4) Tropane : atropine, hyoscine, hyoscyamine, cocaine, pseudo pelletierine.
5) Quinoline : quinine, quinidine, chinchonine, chinconidine, camptothecin.
6) Isoquinoline : morphine, codeine, hydrastine, d-tubocurarine, berberine,
emetine, cephaeline, papaverine, narcotine.
7) Aporphine ; boldine
8) Indole : ergotamine, ergometrine, reserpine, vincristine, vinblastine,
strychnine,brucine,physostimine.
9) Imidazole : pilocarpine, isopilocarpine.
10) Norlupinane : cytisine, laburnine, lupanine, sparteine.
11) Purine : caffeine, theobromine, theophylline.
12) Steroidal : protoveratrine, solanidine, conessine.

PSEUDOALKALOIDS
13) Diterpine : aconitine, aconine, hypoaconitine.

PROTO ALKALOIDS
14) Alkylamine : ephedrine, pseudoephedrine, mescaline, colchicine.

CHEMICAL TEST FOR ALKALOIDS:

1) Mayer’s reagent (potassium mercuric iodide solution ) gives cream coloured
ppt.
2) Hager’s reagent ( saturated solution of picric acid ) gives yellow coloured ppt.
3) Wagner’s reagent ( iodine potassium iodide solution ) gives reddish brown
ppt.
4) Dragendorff’s reagent (potassium bismuth iodide solution) gives reddish
brown ppt.
5) Murexide test : purine alkaloid + Hcl + pot. Chlorate heated in petridish till
dryness. Purple colour is obtained on exposing residue to vapours of
ammonia.Purple colour lost on adding alkali.
 
ISOLATION & EXTRACTION OF ALKALOIDS :

Alkaloids are soluble in different solvents depending on their solubility. Free bases are
soluble in organic solvents & salt forms are soluble in water
Extraction can be done by using various solvents.

1) Extraction with water immiscible solvent : Alkaloids in salt form like tannates,
oxalates is treated with alkali & extracted with water immiscible solvents. Alkaloids in
immiscible solvent is removed by treating with dil. acid. Again with treatment of alkali
& immiscible solvent free alkaloidal bases are obtained in immiscible solvent layer.

2) Extraction with water missible solvent : Grounded drug is treated with methanol,
ethanol, isopropanol. Alcohol dissolves salts & free bases imparting hydrolysing
effect on bases and salts.

3) Extraction with water : drug is extracted with acidified water which is then made
alkaline & alkaloids are removed with the help of immiscible solvents.

Automatic machines used for isolation are mills & extractors.

purification can be done by :
1) Treating with pet.ether
2) Changing pH, filtering with charcoal, treating with heavy metals.
3) Successive washings with pet.ether, alcohol, acetone, chloroform.
 Powdered drug (alkaloid in salt form)
+water
+ base (ammomium hydroxide, calcium hydroxide
Alkaloid converted to free base form

Free base extracted with nonpolar solvents (chloroform)

chloroform or nonpolar phase contains Aq. phase contains acids,

free bases; resins, fats, waxes glycosides,sugars, pigments.
+dil.Hcl

Aq.acidic phase(alkaloidal Chloroform phase(resins, fats, oils)

salts, impurities)

Add ammonium hydroxide & extract with chloroform

chloroform phase (free alkaloidal Aq. Phase

base)

Remove phase & recrystallise alkaloid

 Extraction of indole alkaloid reserpine
Dried root (finely powdered)
Extract with 10 % acetate
buffered with sod. Bicarbonate to pH 3-5
Add liq. Ammonia to make sol. alkaline

Filter formed ppt

filtrate ppt
Dissolve in chloroform
extrate with 2%acetate

Acetate chloroform layer

Treat with 0.5 N sulfuric acid
wash with water

basify aq. Layer

treat with chloroform
evaporate chloroform extract
residue
treat with pet.ether
filter
add 4% citrate sol.
ppt of reserpine
recrystallise pure reserpine obtained
 Extraction of hyoscyamine (tropane alkaloid)
ground drug extract with alcohol residue
treat with ccl4
+ H2O
+ Hcl
stand
(+ methanol if ccl4 does not seperates readily)

test for alk. Content alkaloid in water phase

stand aq. extract decant
clear liquore basified with ammonia
filter
Extract with ethylene dichloride

reextract with 5% dil Hcl

basify with NH4OH

extract with ethylenedichloride

Filter
evaporate under
reduced pressure
Crude drug obtained
 Crude drug

dissolve in dry methanol

treat with charcoal
filter
cool
netralise with sulphuric acid
treat with charcoal
filter
evaporate in vaccum at low temp

Sulfated salts crystallise

If required recrystallise with methanol & charcoal

 Extraction of purine alkaloid
Powdered drug (tea)
boil with water
filter

marc filtrate
boil with water
filter

marc filtrate
combine filtrate (caffine + tannin)
add lead acetate
tannins pptheat
filter
filtrate
add lead acetate
pass hydrogen sulphide gas
excess lead acetate seperates as lead sulfide
Add filter aid
ppted lead sulphite + filtrate
absorbed colouring matter evaporate to 1/3rd volume
extract with chloroform
stand
distill chloroform
true caffeine
recrystallise using alcohol