Alkaloids
Alkaloids
Alkaloids
Alkaloid Definition
Alkaloid: Difficult to define ‘Proto-alkaloid’/ ‘amino-alkaloid’ –
No definitive difference between applied to compounds which
an alkaloid and naturally lack one or more of the
occurring complex amines. properties of typical alkaloids.
If larger amounts of
alkaloids need to be
extracted, one of the
following methods can be
used. TLC plate
Extraction in an Alkaline Medium
Step 1: Powdered, defatted herb is mixed with an alkaline
aqueous solution.
Separation Funnel
Final Step
Organic solvent
containing alkaloid bases
is decanted, freed from
water traces (drying over
anhydrous salt e.g.
sodium sulphate) and
evaporated under
reduced pressure.
A dry residue remains: total
basic alkaloids.
Kava Powder
Alkaloid Extraction in Acidic
Medium
2 Methods possible
Or
Common names:
Stramonium leaf,
Thornapple, Jimson or
Jamestown weed
Datura stramonium - Constituents
Main (Tropane) Alkaloids
* Hyoscyamine
• Hyoscine (2:1)
Younger plants: hyoscine –
predominant alkaloid
Also contains
• Atropine
Common names:
Henbane
Hyoscyamus niger - Constituents
Tropane Alkaloids
Mainly
• Hyoscyamine
• Hyoscine (main
constituent)
Hyoscyamus niger – Allied Drugs
• Hyoscyamus albus
(petiolate stem-leaves
and pale yellow, non-
veined petals – bottom
left).
• Hyosycamus muticus (top
right)
• Hyoscyamus pusillus
• Hyoscyamus aureus
• Hyoscyamus reticulatus
(Indian henbane – bottom
right)
Hyoscyamus niger - Uses
Resembles belladonna
and stramonium in
action – only weaker.
Higher hyoscine content
– less likely to cause
cerebral stimulation .
Also contains
• Scopoletin
• Calcium oxalate
Atropa belladonna
ALLIED DRUGS ADULTERANTS
Indian belladonna Phytolacca decandra
(Atropa acuminata) – Ailanthus glandulosa
yellow-brown flowers
& brown-green
leaves.
Atropa baetica (yellow
flowers and black
berries) – endangered
species
Atropa belladonna - Uses
Used as a sedative
To stop bodily
secretions (e.g.
saliva)
Root preparations are
used externally
Pyridine Alkaloids
Also referred to as
Pyrrolizidine alkaloids
Include
Lobeline (Lobelia herb) –
respiratory stimulant Lobeline
Used in asthma
preparations.
Nicotine (Nicotiana
tabacum and other
Nicotina spp) – toxic
used as an insecticide
Lobelia inflata- Capmanulaceae
Definition: Lobelia herb
consists of the dried
aerial parts of Lobelia
inflata.
Also
Lobelidine
Lobelanine
Isolobelanine
Lobelia inflata - Uses
Asthma
Chronic bronchitis
Anti-smoking preparations
Injection of lobeline
hydrochloride is used in
the resuscitation of
newborn infants.
INCLUDES
C. Succirubra, C. calisaya,
C. ledgeriana, C.
officinalis
Cinchona - History
Historically played an
important role in the
treatment of malaria.
This has now lessened
with the introduction of
synthetic drugs.
Also
• Quinicine
• Cinchonicine
• Cinchotannic acid
• Anthraquinones
BP monograph: opium is
intended only as a starting
point for the manufacture of
galenicals, and should not be
dispensed as such.
Papaver somniferum - Constituents
30 Alkaloids
6 main ones
• Morphine
• Codeine
• Thebaine
• Noscapine
• Narceine
• papaverine
Tests for Opium Alkaloids
Morphine: soluble in
sodium hydroxide
(due to phenols)
Codeine is precipitated
by sodium hydroxide.
Codeine
Milder sedative
Relieve cough
Habitual use may cause
constipation
Also
• Emetamine
• Psychotrine methylether
• Ipecoside (glycoside)
Ipecacuanha - Adulterants
Other “ipecacuanhas”,
different roots said to
have emetic
properties.
These are easily
distinguished from the
original root and are
now very rarely
imported.
Test for emetine
Mix 0.5g powdered herb
with 20ml HCL and 5ml
water.
Filter
To 2ml filtrate add 0.01g
potassium chlorate
Result: if emetine is
present, a yellow colour
appears. After standing
for 1hr, changes to red.
Ipecacuanha Uses
Expectorant
Emetic
Amoebic Dysentry
Emetine is more
expectorant and less
emetic in action than
cephaeline
Controlled field
cultivation on rye is
the main source of
crude drug.
Ergot - History
World-wide, sporadic
reports of ergot
poisoning (ergotism)
still appear in
literature: 1992 an
analysis of rye flour
sold in Canada
showed low levels of
fungus contamination.
Of 128 samples, 118
were contained the
fungus.
Ergot - Constituents
Ergot alkaloids
(ergolines)
Include
• Ergonovine (water-
soluble) Alkaloids
• Ergotoxine &
Ergotamine alkaloids
(water-insoluble)
Ergot Substitutes & Storage
SUBSTITUTES
• Ergot of Wheat
• Ergot of Oats
• Ergot of Diss (reed)
STORAGE
Liable to attacks by insects,
moulds & bacteria.
Dried after collection &
stored in a cool, dry
place. If powdered and
not immediately defatted
– looses lots of its
activity. If defatted – can
keep for an extended
period.
Ergot - Uses
Traditionally used in
labour to assist the
delivery
Reduce post-partum
haemorrhage
Ergometrine produces
oxyticic effects.
Nux Vormica - Loganiaceae
Definition: Nux vormica
consists of the dried, ripe
seeds of Strychnos nux-
vormica, (a tree growing
up 13m in India, Thailand,
South Vietnam and
Cambodia).
Mainly
• Strychine
• Brucine
Strychine is more
physiological active
than brucine
Nux Vormica - Uses
Action of the whole drug
resembles the action of
Strychnine
Formerly used as a
circulatory stimulant
(e.g. in surgical shock)
Now used mainly as a
respiratory stimulant (in
certain cases of
poisoning)
Bitter - used to improve
appetite & digestion
Commonly misused as a
‘General Tonic’
Nux Vormica – Allied Drugs
Ignatius beans (seeds
of Strychnos ignatii) –
fruits are larger than
those of Nux vormica
& may contain up t 30
seeds. Also dark
grey in colour.
Main alkaloid
• Reserpine
Also
• Rauwolfine
• Serpentine
• Serpentinine
DEPRESSION
Protoalkaloids
Alkaloid-like amines.
Have no nitrogen as part
of the hetrocyclic ring.
Examples: ephedrine
and adrenaline
Mainly
Ephedrine
Pseudoephidrine
Also contains
ephedradines –
hypotensive
properties
Ephedra - Uses
Asthma, colds, flu and Above ground parts are
Hayfever medications normally used, although
(action is more prolonged the roots are better to use
than adrenaline. (less alkaloids)
Additional advantage:
need not be given by
injection, but can be
administered orally).
Allopathic: Sinumed (dries
a runny nose)
TCM: Used as an anti-
inflammatory.
Weight loss (increases
metabolism, decreases
appetite – CNS stimulant
– acts on adrenergic
Ephedra - CAUTIONS
Above-ground parts Full medical Hx of pt is
contain higher required: contra-
amounts of alkaloids indicated in DM,
(increase BP) thyroid disease,
glycoma, all cardiac
Side Effects: Causes conditions (including
tremors, hypertension)
nervousness,
palpitations &
tacchycardia.
Khat or Abyssinian Tea
Consists of the fresh
leaves of Catha
edulis.
Cultivated in Abyssinia
and Arabian
peninsula.
Contains protoalkaloids
Khat – Uses and Actions
Traditionally: Fresh leaves are Used as a tea: colds & flu, weight
chewed (mental clarity) and loss, menstrual cramps,
used in the same way as asthma.
cocoa.
Used by students & labourers. Not addictive (leaves are chewed
– juice swallowed – residue
CNS stimulant spat out)
Found in Cocoa
Nutritive/food
Nervous system
stimulant
Diuretic
Theobroma - Uses
Cocao butter is used as
a base for
suppositories and
salves
Chocolate (flavouring)