SAS 8 ALKALOIDS

Names are either obtained from:

1\. generic name of the plant yielding them 2. specific name of the plant yielding them 3. common name of the drugs yielding them 4. physiologic activity 5. occasionally from discoverer

names of all alkaloids should end in

“ine”

poisonous agents

protecting the plants against insects and herbivores

end products

of detoxification reactions representing a metabolic locking-up of compounds otherwise harmful to the plant

regulatory growth factors

regulatory growth factors

supplying nitrogen

reserve substances capable of ________ or other elements necessary to the plant’s economy.

PROPERTIES OF ALKALOIDS

 colourless, crystalline solids

 basic

 having a ring structure

 have definite melting points

 free bases are:

\- soluble in organic solvents and insoluble in water

alkaloidal salts are:

soluble in water and partially soluble in organic solvents

free bases are:

\- soluble in organic solvents and insoluble in water

True Alkaloid

Derive from amino acid and they share a heterocyclic ring with nitrogen.

Protoalkaloid

The Nitrogen atom derived from an amino acid is not a part of heterocyclic

Pseudoalkaloid

The basic carbon skeletons of which are not derived from amino acids. They are connected with amino acid pathways.

Mayer’s Reagent

Mercuric K iodide

Valser’s Reagent

Mercuric iodide

Wagner’s Reagent

Iodine in KI

Dragendorff’s reagent

K bismuth iodide

Marme’s reagent

Cadmium KI

Sonnenscheins’s Reagent

Phosphomolybdic acid

Scheibler’s Reagent

Phosphotungstic Acid

Tannic acid

Tannic acid

Gold salts

Gold salts

Picric acid

Hager’s test

CLASSES OF ALKALOIDS

* PYRIDINE - PIPERIDINE ALKALOIDS
* TROPANE ALKALOIDS
* QUINOLINE ALKALOIDS
* ISOQUINOLINE ALKALOIDS
* INDOLE ALKALOIDS
* IMIDAZOLE ALKALOIDS
* STEREOIDAL ALKALOIDS
* STEROIDAL ALKALOIDS
* ALKALOIDAL AMINE
* PURINE BASE

3 sub-groups

Derivatives of

1\. piperidine; lobeline from lobelia

2\. pyridine and pyrrolidine; nicotine from tobacco

3\. nicotinic acid; arecoline from areca

Other name for Tobacco / Nicotine

 Roots of Nicotiana tabaccum

EFFECTS OF TOBACCO / NICOTINE

 CNS stimulant

 Cholinergic agent

 Hydrocarbons : benzopyrene and tar (carcinogenic)

Tobacco / Nicotine

 The most important constituent:

Nicotine,

nicotianine,

nicotinine,

nicoteine, & nicoteline.

Lobelia /Indian tobacco

 Consists of the dried leaves and tops of *Lobelia inflata*

Lobelia

was employed by the Indians, when necessity required, as a substitute for tobacco.

14 alkaloids

The drug contains ________, of which lobeline is the major and most important.

Betel nut / Areca nut / Areca

Is the dried, ripe seed of Areca catechu, Fam. Palmaceae

Arecoline

the most abundant and physiologically most active alkaloid; CNS stimulant

USE of Betel nut / Areca nut / Areca

 Anthelmintic in veterinary practice and is employed as a vermicide and taenifuge.

Belladonna / Deadly nightshade leaf

Consists of the dried leaf and flowering or fruiting top of Atropa belladonna , fam. Solanaceae

Atropine

antimuscarinic

peptic ulcer

The drug is used as adjunctive therapy in the treatment of ______, functional digestive disorders, ulcerative colitis and diarrhea

Hyocyamus / henbane/ Hog’s bean

Is the dried leaf with or without the stem and flowering or fruiting top of Hyocyamus niger, fam Solanaceae

Cons for Hyocyamus / henbane/ Hog’s bean

 Hyoscyamine

 Scopolamine

 Atropine

USE for Hyocyamus / henbane/ Hog’s bean

• Parasympatholytic

Egyptian henbane

The dried leaves and floweing tops of Hyocyamus muticus

2) Egyptian henbane

The plant yields bout 1.5% of total alkaloid, consisting primarily of Hyoscyamine.

Stramonium/ Jimson / jamestown weed

Consists of the dried leaf and flowering tops with branches of Datura stramonium

Withania

is the dried root of Withania somnifera (Fam Solanaceae)

ACTIVE CONTITUENTS FOR “WITHANIA”

 Tropine

 Pseudotropine

 Hygrine

2) Withania

Used as a sedative

Duboisia

Consist of the dried leaves of Duboisia myoporoides

2) Duboisia

Commercial source of atropine

Pituri / Australian tobacco

 Is the leaf of Duboisia hopwoodii

 Used in australia like tobacco

 It contains Nicotine and nornicotine

Mandragora / European mandrake

 From the root of Mandragora officinarum

 It contains hyoscyamine, scopolamine, and mandragorine.

Dried leaves of Erythroxylum coca – Commercially known as?

Huanuco

Dried leaves of Erythroxylum truxillensecommercially known as?

Truxillo coca

PREPARATION FOR “Cocaine / Coca / Coca Leaves”

semi-synthesis from plant derived ecgonine.

 local anesthetic

Brompton’s cock

cocaine HCL

 Used for patients with terminal cancer for the purpose of relieving pain

Cinchona succirubra - cinchonidine

Is the dried bark of the stem or of the root of_______?

Yellow cinchona

Cinchona calisaya- quinine

Cinchona bark/Peruvian bark

Fam Rubiaceae

Cinchona bark/Peruvian bark

The alkaloids are chiefly formed in the parenchymal cells of the middle layers of the bark.

USE AND DOSE OF “**Cinchona bark/Peruvian bark”**

 malaria fever

 In some places it is also employed as effervescent tonic water.

 Quinidine is now the principal cinchona alkaloid employed therapeutically.

 Cinchona was formerly given in doses of 1g.

 Cinchonism- cinchona alkaloid toxicity

Cuprea bark

Is from Remija purdieana

2) Cuprea bark

Commercial source of Quinidine

Ipecac

From the rhizome of Cephaelis ipecacuanha

Aka Rio / brazilian ipecac

\[IPEC\] From the rhizome of

Cephaelis acuminata

Cephaelis acuminata

Aka Nicaragua ipecac/ panama ipecac/ cartagena ipecac

• Cephaeline

• Psychotrine

• Emetine (primary)

– Powerful stimulant emetic and antiamoebic Ipecac 3 primary alkaloids

Ipecac 3 primary alkaloids

USE OF IPECAC

used in the treatment of drug overdose and in certain poisonings.

DOSE OF IPECAC

15 ml, followed by 2 glasses of water.

Ipecac + Opium =?

Dover’s Powder- acts as diaphoretic

Pharmaceutical Products

\- Emetine/ methylcephaeline

\- Emetine Hydrochloride

Emetine/ methylcephaeline

is an alkaloid obtained from ipecac or prepared synthetically by methylation of cephaeline.

Emetine Hydrochloride

is a hydrated hydrochloride of emetine. It is an antiamoebic and acts primarily in the intestinal wall and in the liver

Hydrastis / Golden seal

From the dried rhizome and roots of Hydrastis canadensis

Hydrastis / Golden seal

\- 3 types of alkaloids has been isolated from the plant -

\- Hydrastine, berberine – astringent

\- Canadine- anti-inflammatory agent

From the dried rhizome?

Sanguinaria canadensis

Sanguinarine

• Emetic and stimulant expectorant

Tubocurarine / Curare

South American arrowhead poison

 The extract from the bark and stems of?

Strychnos toxifera & Strychnos castelnaei

(+)-Tubocurarine-

the most important constituent, is a quaternary compound that contains a Bisbenzylisoquinoline structure.

Characteristics of (+)-Tubocurarine

 Anti-nicotinic

 Ganglionic blocker

 Skeletal muscle relaxant

 Anticonvulsant from strychnine poisoning of tetanus.

 It is standardized by the **“headdrop**” crossover test in rabbits.  DOSE: 200-400microgram/kg of BW

Opium/ gum opium

The plant contains 30 different alkaloids, the most important of these are;

Morphine 4-21%

Codeine 0.8-2.5%

Noscapine 4-8%

Papaverine 0.5-2.5%

Thebaine 0.5-2%

The dried milky exudate obtained by incising the unripe capsules of?

\- Papaver somniferum

\- Poppyseed

Test for **Opium/ gum opium**

Ferric Chloride test (red color due to meconic acid)

USE FOR **Opium/ gum opium**

CNS stimulant, analgesic, hypnotic, checks excessive peristalsis.

Who first studied this plant for steroidal components?

SERTURNER

Paregoric /camphorated Opium tincture - ?

antipersitaltic

Laudanum

opium tincture

Morphine

most important opium alkaloid

USES OF MORPHINE

narcotic analgesic, hypnotic.

AE: nausea vomiting and constipation

Codeine / methyl morphine

most widely used: antitussive

Heroine / diacetylmorphine

habit forming ; more pronounced effects than morphine

Apomorphine Hydrochloride-

Morphine + HCL in a sealed tube; used as an emetic

Papaverine

smooth muscle relaxant

Hydromorphone

powerful narcotic analgesic, strong respiratory depressant

Diphenoxylate + loperamide

antidirarrheal

Meperidine + Fentanyl

anesthetic

Noscapine (narcotine)

exists as a free base.

It possesses no narcotic properties and is therefore sometimes called “**anarcotine”**

Rauwolfia serpentina

From the dried root of Rauwolfia serpentina

 Reserpine

 Antihypertensive

 Can cause depression and sedation due to its ability to cross BBB

Rescinnamine

an alkaloid that occurs in several species of Rauwolfia

Desperidine

an alkaloid from the root of R. canescens

Catharantus/ vinca

– Is the dried whole plant of Catharantus roseus

– Periwinkle plant

– Source of Vincristine and Vinblastine

Catharantus/ vinca

\- Antineoplastic agent

\- Antimitotic agent