CHARACTERISTIC OF ALKALOIDS

1. Free alkaloids are sparingly soluble in H2O

2. Combine directly with acids to form salts
3. Form highly insoluble precipitates with salts
of heavy metals.
4. Basic nitrogenous of plant origin that are
physiologically active
5. Na2CO3- added to convert alkaloidal salt into
free base
6. Solid alkaloid- white in color, soluble or slightly soluble
in H2O, soluble in organic solvents
7. Pure alkaloids- insoluble in water, soluble in organic
solvents
8. alkaloids+acids- alkaloidal salts
(soluble in water)

9/7/13
Alkaloids yielding plants:
Leguminosae
Ranunculaceae
Solanaceae
Papaveraceae
Rubiaceae
Berberidaceae
Free alkaloids:
Gymnosperms
Taxaceae
Liquid alkaloids
-nicotine
-coniine


9/7/13
The names of the alkaloids are obtained in various
ways:
1. From the generic name of the plant (Hydrastine,
Atropine)
2. From the specific name of the plant (Coccaine,
Belladona)
3. From the common name of the drug (Ergotamine)
4. From their physiologic activity (Emetine,
morphine)
5. Occasionally from the discoverer (Pelletietine)



FUNCTIONS OF ALKALOIDS IN PLANTS
a. poisonous agents protecting plants against insects
and herbivores
b. end products of detoxification reaction
representing
- metabolic locking up of compounds otherwise
harmful to the plant
c. Regulatory growth factor
d. Reserve substance capable of supplying nitrogen or
other elements necessary to the plant economy.

9/7/13
Alkaloidal reagents/precipitants:
mercuric potassium iodide TS known as Mayers
reagent - white or slightly yellow ppt.
marmers rgt. potassium cadmium iodide-
white ppt.
dragendorffs rgt.- potassium bismuth iodide
-orange
Iodine TS is commonly known as Wagners reagent
yields reddish brown or red brown ppt.

Scheiblers rgt.- phosphotungstic acid
- yellowish or brownish
AuCl- white or yellowish precipitates/
Mercuric iodide TS commonly known as Valsers reagent
(KI and mercuric iodide white ppt.
tannic acid - white or yellowish, flocculent compounds
picric acid (Hagers)- yellow
Sonnenscheins rgt. phosphomolybdic acid
- yellowish or brownish-yellow solids

9/7/13
Pharmacologic Action of Alkaloids
Analgesic and narcotics-morphine, codeine
Central stimulant- strychnine, brucine
Mydriatics- atropine
Miotics physostigmine, pilocarpine
Cause a rise in B.P - ephedrine
Excessive hypertension- reserpine












.
.




The following plant is based on the ring structure
or nucleus of the chief alkaloid group in the
plant drug.
1. Pyridine piperidine alkaloids

N N
H
Tropane



9/7/13
NCH
3
OH
Quinoline
N
Isoquinoline




Indole

9/7/13
N
N
H
Imidazole



Steroid


9/7/13
N
N
Alkaloidal amine





Purine alkaloid

9/7/13
N
N
N
N
H
Purine
1
2
3
4
5
6
7
8
9
CH
2
CH CH
3
NH
2
Properties of alkaloids
1. Free alkaloids are sparingly soluble in H2O.

2. Combine directly with acids to form salts

3. Forms highly insoluble ppts. with salts of heavy
metals.
1. Pyridine- PIPERIDINE ALKALOIDS
ARECA
BO: Areca Catechu, Palmae
Syn: Areca nut, Betel nut
AC: Arecoline
Use: Anthelmintic in veterinary practice as vermicide
& vermifuge


9/7/13
LOBELIA
BO: Lobelia inflata, Lobeliaceae
Syn: Indian tobacco
AC: Lobeline
Use: Aid in breaking the tobacco habit incorporated in
the tablets and lozenges that intended to aid in
breaking the tobacco habit.

9/7/13
9/7/13
NICOTINE
BO: Nicotiana tabacum, Solanaceae
Named after Jean Nicot , French diplomat who
intoduced tobacco in Europe.
- bound to an ion-exchange resin in a
chewing gum base to aid smokers in giving up
smoking.

9/7/13
TROPANE ALKALOIDS

BELLADONNA
BO: Atropa belladona, Solanaceae
Syn: Deadly nightshade leaf
AC: Hyoscyamine
Use: acts as a parasympathetic depressant
9/7/13
9/7/13
Principal Solanaceous alkaloids
-hyoscyamine- when racemized during extraction is
converted to atropine
-atropine
-scopolamine or hyoscine an anticholinergic
Rudolf Brandes- discovered codeine & isolation of
atropine with Philip Geiger




STRAMONIUM
BO: Datura stramonium, Solanaceae
Syn: Jimson weed, Jamestown weed
AC: Hyoscyamine
Use: Anticholinergic
Powder of this alkaloid is burned, the resultant vapor is
Inhaled for the relief of asthma.
9/7/13
9/7/13
COCAINE
BO: Erythroxylum coca, Erythroxylaceae
Syn: Coca
AC: Ecgonine, tropine , and hygrine
Use: Psychomotor stimulant with a strong abuse
potential
Cocaine has a long duration of local anesthetic
action because it is a vasoconstrictor
9/7/13
QUINOLINE ALKALOIDS
CINCHONA
BO: Cinchona succiruba, Rubiaceae
Syn: Peruvian bark
AC: Quinine. quinidine , cinchonine, cinchonidine
Quinidine- principal cinchona alkaloid employed
therapeutically at present as anti-arrthythmic agent
Quinine- quinoline alkaloid employed for malaria


9/7/13
9/7/13
Identification of the quinine /quinidine by
Thalleioquin test
- addition of 2 drops of bromine T.S. to 5ml. Sat.
soln. of quinine/quinidine or 1:100 soln. of their
salts followed by NH3 T.S
ISOQUINOLINE ALKALOIDS Emerald
green color of thalleioquin - discovered by
Joseph Caventou collaborated Pelltie
IPECAC
BO: Cephalis ipecacuanha, Rubiaceae
AC: Emetine, Cephaeline, Psychotrine
Use: treatment of drug overdose and in certain
poisoning (emetic)
- Form of syrup is used in the treatment of drug
overdose in certain poisonings


9/7/13
HYDRASTIS
BO: Hydrastis canadensis, Ranunculaceae
Syn: Golden deal
AC: Hydrastine
Use: astringents in inflammation of the mucous
membrane

9/7/13
9/7/13
SANGUINARIA
BO: Sangunaria canadensis, Papaveraceae
Syn: Blood root
AC: Sanguinarine (about1%), chelerythrine,
protopine and allocryptopine
Use: Stimulating expectorant & emetic
prorperties


9/7/13
OPIUM: Paracelsus referred opium as the stone of
immortality
BO: Papaver somniferum
Syn: opium or gum opium
AC: meconic acid
Use: stimulate and depresses CNS

9/7/13
9/7/13
Alkaloids of Opium
1. morphine- most important of the opium
alkaloids
Use: narcotic analgesics
2. codeine most widely used in opium alkaloid
(methyl morphine)-derivative of morphine
- discovered by Pierre Robiquet
-antitussive principle
3. Diacetylmorphine or heroin
- is formed by the acetylation of morphine

4. Papaverine used in principally for the relief of
cerebral and peripheral isehemia associated with artyerial
spasm & myocardial ischemia complicated by arrhythmias

5. Hydromorphine
6. Hydrocodone
9/7/13
INDOLE ALKALOIDS
RAUVOLFIA SERPENTINA
BO: Rauvolfia serpentina, Apocynaceae
AC: reserpine
Use: Antihypertensive/psychotherapeutic alkaloid
Other alkaloids found in other species of Apocynaceae
- Officially used as an adjunct in psychotherapy

9/7/13
1. Rescinnamine
chemically it is methyl reserpate ester of
3,4,5 trimethoxycinnamic acid
Use: treat mild essential hypertension

2. Deserpidine (canescine, recanescine)
chemically it is II-desmethoxyreserpine

3. Yohimbine
Use: treat impotence in patients with vascular or
diabetic problems
product: serpasil


9/7/13
9/7/13
CATHARANTHUS-exerts antineoplastic action by
interfering with the polymerization of tubulin
into microtubules
BO: Catharanthus roseus , Apocynaceae
Syn: vinca
AC: vinblastine , vincristine
Use: antineoplastic/oncolytic
USP official alkaloids with oncolytic
action/anticancer
Leurocristine , Vinblastine ,Vinca leukoblastin

9/7/13
NUX VOMICA
BO: Strychnos nux-vomica , Loganiaceae
AC: Strychnine, brucine (dimethyoxystrychnine)
Use: strychnine (extremely toxic)- vermin killer
brucine- commercially as an alcohol denaturant
because it is extremely bitter and CNS stimulant

9/7/13
PHYSOSTIGMA
BO: physostigma venenosum, Fabaceae
Syn: Physostigma, calabar bean,
Ordeal bean
AC: Physostigmine (eserine)- major alkaloid eseramine ,
geneserine , physovenine
Use: employed in ophthalmology to treat glaucoma and
miotics

9/7/13
9/7/13
ERGOT- organisms uses in the parasitic method of
producing ergot alkaloids
BO: Claviceps purpurea, clavicipitaceae
Syn: rye ergot, secale cornutum
AC: ergotoxine , ergonovine, ergotamine
(H2o insol.) (H2o soluble) (H2o insol.)
Use: ergonovine-oxytocic (uterine contraction)
ergotamine-prevent or abort vascular headache
including migrane
9/7/13
IMIDAZOLE ALKALOIDS
PILOCARPINE
BO: Pilocarpus jaborandi, Rutaceae
Syn: pilocarpus ,m jaborandi
Use: Cholinergic drug used in the treatment of
glaucoma
-miotic


9/7/13
STEROIDAL ALKALOIDS
VERATRUM VIRIDE
BO: Veratrum , viride, Liliaceae
Syn: American or green hellebore
AC: Group I
cevadine , germidine , neogermitrine,
neoprotoveratrine, protovevatrine, vceratridine

9/7/13
Group II
pseudojervine, veratrosine
Group III
germine , jervine, robjervine, veratramine
Uses: hypotension , cardiac depressant & sedative
properties



9/7/13
9/7/13
WHITE HELLEBORE
BO: Veratrum album, Liliaceae
Syn: European hellebore
AC: proveratrive a&B
Use: hypotensive properties
insecticides (crude drug)


9/7/13
ALKALOIDAL AMINES

EPHEDRINE
BO: Ephedra sinica, Gnetaceae
Syn: Ephedra, mahuang
AC: Ephedrine
Use: potent sympathommetic that stimulates alpha, beta
& beta 2 adrenergic receptors.

9/7/13
9/7/13
COLCHICUM
BO:Colchicum autumnate, Liliaceae
Syn: Colchium seed
AC: Colchicine
Use: suppresant for gout


9/7/13
OTHER ALKALOIDAL DRUGS
Khat or Abyssinian Tea
BO: Catha edulis, celastraceae
AC: cathinone

9/7/13
9/7/13
Peyote or mescal buttons
BO: Lophophora williamsii, castaceae
AC: mescaline (3,4,5 trimethoxy B
phenylethylamine
Use: psychotomimetic


9/7/13
PURINE BASES
Caffeine containing Drugs
1. Kola, cola or Kola nuts
BO: Cola nitida, sterculiceae
AC: caffeine, theobromine

9/7/13
9/7/13
2. Coffee bean coffee seed
BO: Coffee arabica, Rubiaceae
AC: caffeine
CAFFEINE (xanthine alkaloids)
-does not react w/ or ppt with alkaloidal
reagnents.
BO: Coffea Arabica, Rubiaceae
Syn: 1,3,7 trimethylxanthine
Use: CNS stimulants
9/7/13
Caffeine occurs in :
o Coffee
o Tea
o Cacao
o Guarana
o Kola
o mate

9/7/13
THEOPHYLLINE (xanthine alkaloids)
BO: Camella sinensis, theaceae
Syn: Thea , tea , 1,3 dimethyl xanthine
Use: muscle relaxants for symptomatic relief or
prevention of bronchial asthma

9/7/13
THEOBROMINE
BO: theobroma cacao , Sterculiaceae
Syn: 3,7 dimethyl xanthine
Use: diuretic , smooth muscle relaxant
Preferred over caffeine in the treatment of cardiac edema
and agina pectoris because it has little stimulant action
on the CNS.

9/7/13
9/7/13
ALKALOIDAL precipitants
Caffeine (purine derivative) does not ppt. with
alkaloidal precipitants.
-detected by means of a Murexide test
Mixing a small amt. KLClO3 + a drop of HCl
evaporate to dryness exposing the residue to
NH3 vapor purple color
Miotics
are eye drops that stimulate the parasympathetic
nervous system causing the pupil of the eye to
become smaller.
They reduce intraocular pressure by increasing the
outflow of eye fluids from the eye and they are
usually used to reverse angle-closure glaucoma or
prevent angle-closure in eyes with narrow chamber
angles.
Pilocarpine (one of the miotics) has been used for
almost 150 years for the treatment of glaucoma. It is
rarely utilized today to treat open-angle glaucoma.

9/7/13
Emetic
an agent that causes vomiting
Mydriatic
a drug that dilates the pupil
Vasoconstrictor
a substance that narrows blood vessels by constricting
the smooth muscle in the walls; increases blood pressure


9/7/13
Anticholinergic
an anti-cholinergic agent that functions by
competing with the neurotransmitter acetylcholine
for its receptor sites at synaptic junctions.
Anticholinergics are used to treat spastic disorders of
the GI tract, to reduce salivary and bronchial
secretions before surgery, or to dilate the pupil. Some
anticholinergics reduce parkinsonian symptoms but
are never considered primary agents for therapy.
Atropine in large doses stimulates the central
nervous system and in small doses acts as a
depressant. Among numerous cholinergic blocking
agents are atropine, belladonna, glycopyrrolate,
hyoscyamine, methixene hydrochloride,
trihexyphenidyl hydrochloride, and scopolamine.

9/7/13
Analgesic and Narcotics
Narcotic agents are potent analgesics which are
effective for the relief of severe pain. Analgesics are
selective central nervous system depressants used to
relieve pain. The term analgesic means "without pain".
Even in therapeutic doses, narcotic analgesics can
cause respiratory depression, nausea, and drowsiness.
Long term administration produces tolerance, psychic,
and physical dependence called addiction.
9/7/13
Ergotamine

The combination of ergotamine and caffeine is used to
prevent and treat migraine headaches. Ergotamine is
in a class of medications called ergot alkaloids. It
works together with caffeine by preventing blood
vessels in the head from expanding and causing
headaches.
9/7/13
Brand names of combination products
Cafatine

Rectal Suppository (containing Caffeine,

Ergotamine)

Cafergot

(containing Caffeine, Ergotamine)

Cafergot

Rectal Suppository (containing Caffeine,

Ergotamine)

Cafetrate

Rectal Suppository (containing Caffeine,

Ergotamine)

Ercaf

(containing Caffeine, Ergotamine)

Migergot

Rectal Suppository (containing Caffeine,

Ergotamine)
Wigraine

(containing Caffeine, Ergotamine)

9/7/13
Morphine Oral
Avinza
Kadian
MS Contin
Oramorph SR
Roxanol
Roxanol-T

Epinephrine Injection
Adrenalin Chloride Solution
EpiPen Auto-Injector
EpiPen Jr. Auto-Injector

9/7/13
Hyoscyamine
Anaspaz
Cystospaz
Cystospaz-M
Hyosol SL
Hyospaz
Levbid
Levsin
Levsin Drops
Levsin/SL
Levsinex Timecaps
NuLev

Atropine Ophthalmic
Atropine Care 1%
Atropisol
Isopto Atropine
Ocu-Tropine

9/7/13
Papaverine
-Para-Time SR

Morphine Rectal
-RMS
Reserpine
-Serpalan
-Serpasil

Codeine
-Dihistine
-Nucotuss

9/7/13