OBJECTIVES

To enumerate the different important alkaloids under

isoquinoline.

To determine the sources and importance of different alkaloids.

Isoquinoline is a heterocyclic aromatic organic compound. It is a
structural isomer of quinoline.

Isoquinoline and quinolone are benzopyridines which are composed of a

benzene ring fused to a pyridine ring.

It is a colorless hygrospic liquid with a strong odor.

It is also an alkaloid from various plant species including Mentha

species. Also present in cocoa, black tea, and scotch whiskey.
Isoquinoline is a heterocyclic aromatic organic compound. It is a structural
isomer of quinoline.

Isoquinoline and quinolone are benzopyridines which are composed of a

benzene ring fused to a pyridine ring.

It is a colorless hygrospic liquid with a strong odor.

It is also an alkaloid from various plant species including Mentha species.

Also present in cocoa, black tea, and scotch whiskey.
 It is only slightly soluble in cold water but dissolves
readily in hot water and most organic solvents.
Chemical Formula: C9H7N

Structural Formula:
 USES:

Used in the manufacture of dyes, paints, insecticides and antifungals.

It is also used as a solvent for the extraction of resins and terpenes and as a corrosion inhibitor.
BIOSYNTHESIS OF
ISOQUINOLINE
IPECAC
Consist of the dried rhizome and roots of Cephalis ipecacuanha, known in commerce as Rio or Brazilian Ipecaccac, or
Cephalis acuminata, known in commerce as Cartagena Nicaragua or Panama ipecac (fam. Rubiaceae).

Ipecac yield NLT 2% of the ether- soluble alkaloid of ipecac.

IPECAC
Consist of the dried rhizome and roots of Cephalis ipecacuanha, known in commerce as Rio or Brazilian Ipecaccac, or
Cephalis acuminata, known in commerce as Cartagena Nicaragua or Panama ipecac (fam. Rubiaceae).

yield NLT 2% of the ether- soluble alkaloid of ipecac.

 IPECAC
CEPHAELIS IPECACUANHA
IPECAC
Cephalaes- is from the Greek words, meaning head, and to collect or roll up, and refers to the inflorescence.

Ipecacuanha- is Portuguese from the Brazilian Indian ipekaaguene, meaning a creeping plant that causes vomiting.

Acuminata- refers to the acute apex of the leaf.

Adverse effect :
* Prolonged vomiting

* Aspiration

* CNS depression

* Mallory-Weiss tear

* Delay of other therapy (charcoal/N-

acetylcysteine)

* Pneumomediastinum

* May cause vomiting-induced vagal

bradycardia
 USES:

In form of syrup, used in the treatment of drug overdose and in certain poisonings.

Produce emesis through local irritant effect on GI mucosa.

EMETINEA
EMETINE HYDROCHLORIDE
Is a hydrated hydrochloride of emetine.

It occurs as a white, odorless, crystalline powder that becomes yellowish when exposed to light.

It is freely soluble in water and alcohol.

EMETINE HYDROCHLORIDE
 USES:

Anti-amebic and acts primarily in the intestinal wall and the liver.

Inhibits polypeptide chain elongation, thereby blocking protein synthesis.

Anti-protazoan

Treatment of amebic dysentry, pyrrhea alveolaris, and other amebic disease.

EMETINE

Emetine or methylcephaeline
Is an alkaloid obtain from ipecac or prepared synthetically by methylation
of cephaeline.

It was discovered by Pelettier and Magendie in 1817.

HYDRASTIS
 HYDRASTIS

Hydastis or goldenseal consist of the dried rhizome and roots of Hydrastis Canadensis Linne
(Fam. Ranunculaceaa)

Hydrastis is greek means and means to accomplish or act with water, the specific efers to
the habitat. The rhizome and roots show a golden yellow color. Goldenseal was plentiful
in the forests of the eastern of United States and Canada. Goldenseal has been cultivated
in Oregon, Washington, North Carolina, Tennesse, Michigan, Wisconsin and other
localities. The plants, propagated from rhizome buds, require 3 to 4 years to produce
marketable drug.
HYDRASTIS

Three alkaloids have been isolated from hydrastis: hydrastine, berberine, and
canadine.

Use:

The hydrastis alkaloid, hydrastine and berberine, are used as astringent in

inflammation of the mucous membranes.

Hydrastine is readily soluble in choloform, alcohol, and eher but most insoluble in
water. It crystallizes in prisms, melting at 131 to 132C
 SANGUINARIA

Sanguinaria or bloodroot is the dried rhizome of Sanguinaria Canadensis Linne (Fam. Papaveracea.) Generic name is from
sanguinarius, meaning bloody, and refers to the color of the juice: Canadensis refers to the plant habitat in Canada.

The plant is a low perennial herb with a horizontal branching rhizome that bears slender roots and contains an orange-red latex.
The rhizomes are dug during the early summer, deprived of their roots, and carefully dried. The plant grows in the rich oen
woodlands in North America east of the Mississippi.
 SANGUINARIA

* Blood root was used by the Indians to stain their faces and was also used as an acrid emetic. It is use in
homemade cough remedies.

* Sanguinaria contains alkaloids of the protopine series, including sangunarine (about 1%) chererythrine, protopine,
and allocryptopine. These alkaloids are colorless but tend to form colored salts and yields reddish salts with nitric
orsulfuric acids; yellowish salts are formed with chlerythrine.

* All sangunaria are found in other members of Papaveracea. Species of the families Ranunculacea, Berbeidacea,
Menispermacea, and Papaveraceae contains alkaloids of this type.
SANGUINARIA
Uses:

Stimulating expectorant and emetic properties.

Doses:

Usual dose 125 mg.

Prescription product:

Prunicodeine
TUBOCURARINE CHLORIDE
CHEMICAL FORMULA: C37H52CL2N2O11

CHEMICAL STRUCTURE:
Curare or South American arrow poison is a crude dried extract.
A toxic alkaloid obtained chiefly from the bark and stems
(Chondrodendron tomentosum of the fam.(Menispermaceae)
that in its dextrorotatory form constitutes the chief active
constituents of curare and has been used in skeletal muscle
especially as an adjunct to anesthesia in surgery.
Any given sample of the drugs contains at least several of a large possible
number of alkaloids and quartenary compounds, but the specific composition
varies according to the identity of the plant material from which it was
prepared.

(+)- Tubocurarine, the most important constituent, is a quarternary compound

that contains a bis- benzylisoquinoline structure.
It is only slightly soluble in cold water but dissolves readily in hot
water and most organic solvents.
Tubocurarine chloride or (+)- tubocurarine chloride is a white or
yellowish white to grayish, odorless, crystalline powder. It is
derived from the tube curare and was first isolated by Boehm in
1898 and later by King in 1947. King obtained it from
Chondodendron tomentosum and confirmed the structure as a
quartenary ammonium compund.
USES:

Tubocurarine chloride is employed as a skeletal muscle relaxant to

secure muscle relaxation in surgical procedures without deep
anesthesia. Also, it is used to control convulsions of strychnine
poisoning and of tetanus; it is an adjunct to shock therapy in
neuropsychiatry and a diagnostic aid in myasthenia gravis.
 USES:
Special Concerns: use with caution during pregnancy and lactation and in children. If repeated doses are used before delivery, the
newborn may manifest decreased skeletal muscle activity. Children up to 1 month of age may be more sensitive to the effects of
tubocurarine. Use with extreme caution in clients with renal dysfunction, liver disease, or obstructive states.
Additional Side Effects: Allergic reactions. Excessive secretion and circulatory collapse.
Overdose Management: Treatment: Overdosage chiefly treated by artificial respiration, although neostigmine, atropine, and
edrophonium chloride should also be on hand.
 OPIUM

A dried latex obtained from the opium poppy. (Papaver somniferum).

From the greek word opion meaning poppy juice. Papaver is the latin name for poppy and somniferum means
produce sleep.
An annual herb with large, slowly, solitary flowers that vary in color from white to pink or purple.

Plants that produce lighter color seeds have been classified as variety album, but its designation is not employed in
the modern taxonomic writings.
OPIUM POPPY SEED
The plant was first cultivated somewhere in the northeastern
corner of the mediterranean region, were opium was first
produce.
First recorded cultivation of opium poppy in india dates
from the 15 century, and the cultivation began in macedonia
and persia(Iran) middle of 19 century.
The discovery of the medicinal qualities of opium is lost in
antiquity.
Cultivation of opium is controlled internationally by the
International Narcotics Control Board of the United Nations.
 ALKALOIDS OF OPIUM

Morphine
Codeine
Heroine
Aphomorphine hydrochloride
Papaverine
Hydromorphone hydrochoride
Hydrocodone bitartrate
Noscapine
Morphine

The most important opium alkaloid, contains a phenolic and an alcoholic hydroxyl group.

Occurs white silky crystal, cubic masses and fine crystalline powder. Stable in air,

odorless and bitter tasting.

They are strong hypnotic and narcotic.

Centrally acting analgesics, in most cases, have certain structural features in common.

They are quaternary, phenol group attached to this carbon atom, a tertiary nitrogen atom

and 2-carbon bridge separating the tertiary atom and central carbon atom.
Codeine
The most widely used opium alkaloid. May be either obtained from opium or
prepared from morphine by methylation or from thebaine by appropriate
reduction and demethylation.

A methylmorphine in which the methyl group replaces the hydrogen of the

phenolic hydroxyl group.

Effloresces in air, used as sedative, especially in allaying coughs.

Dose of codeine sulfate and codeine phosphate is

Anagelsic 15-60 mg every 4 hrs.or as needed. Antitussive ,

10-20 mg every 6 hrs. as needed.

Heroine
Also known as Diacetylmorphine.

Formed by acetylation of morphine.

Action is similar but more pronounced than that of morphine.

Its manufacture in the US is forbidden by law and its use in medicine has been discontinued.
Apomorphine hydrochloride

Formed when morphine is treated with hydrochloric acid in a sealed tube, and one molecule of water is lost.

An emetic and is particularly valuable in cases of poisoning .

Decomposes readily and must be rejected if an emerald green color is produced when it is shaken with distilled water.
 Papaverine

Occurs naturally in opium to extent of about 1%, but it may also produced synthetically.

Papaverine hydrochloride is odorless but has a slightly bitter taste.

A smooth muscle relaxant.

Usual dose orally is 150mg.

It is also used as antitussive in combination with codeine sulfate.

Hydromorphone hydochloride

Also known as hydromorphinone hydrochloride.

It is prepared by reducing morphine in hydrochloric acid solution with hydrogen in the presence of catalyst.

The drug is a powerful narcotic analgesic and tends to strongly depress the respiratory mechanism.
HYDROMORPHONE HYDOCHLORIDE
Also known as hydromorphinone
hydrochloride.

It is prepared by reducing morphine in

hydrochloric acid solution with
hydrogen in the presence of catalyst.

The drug is a powerful narcotic

analgesic and tends to strongly
depress the respiratory mechanism.
HYDROCODONE BITARTRATE
Hydrocodone bitartrate
Also known as Di-hydrocodeinone bitartrate.

It classed as antitussive and is excellent aid in treating a troublesome cough.

Also known as Di-hydrocodeinone bitartrate.
Usual dose is 5-10 mg,3-4 times a day , as necessary.
It classed as antitussive and is excellent aid in treating a troublesome cough.
Its represented product is Hyocodan and tussend.
Usual dose is 5-10 mg,3-4 times a day , as necessary.

Its represented product is Hyocodan and tussend.

Noscapine
Commonly called as narcotine and anarcotine.

exist in opium as a free base

An antitussive, usual dose is 15mg, up to 4 times a day.

Available in syrup and chewable tablets.

Ex. Are Conar, Actol

Chemical Formula: C9H7N

Structural Formula:
 USES:

Used in the manufacture of dyes, paints, insecticides and antifungals.

It is also used as a solvent for the extraction of resins and terpenes and as a corrosion inhibitor.
Noscapine

Commonly called as narcotine and anarcotine.

exist in opium as a free base

An antitussive, usual dose is 15mg, up to 4 times a day.

Available in syrup and chewable tablets.

Ex. Are Conar, Actol

REFERRENCES:

http://www.mayoclinic.org/drugs-supplements/ipecac-syrup-oral-route/description/drg-20064363

http://reference.medscape.com/drug/ipecac-syrup-343735

V.TYLER.,PHARMACOGNOSY WITH ORGANIC CHEMISTRY

9TH edition.