Chemical properties

The substitution on the nitrogen atom

R2 NH2 R R H N R2 R N R3 R R2

+ R3
N R4

1ry

2ry

3ry

Clquaternary

The state of the alkaloid

NH2 R R

R2 N

+
NH3

O
R3

Free base

Cl-

Salt form

N-oxide

Classification

Non-heterocyclic or atypical alkaloids or biological amines

NH2 H3CO CH2 C H2

H3CO OCH3

Mescaline

Heterocyclic or typical alkaloids: divided into groups according to their ring structure

H N

H N N N

pyrrole
H N

pyrrolidine

pyrrolizidine

pyridine

NMe N N

piperidine

tropane

quinoline

isoquinoline

N H

N H

N H

indole

indolizidine

imidazole

NMe

aporphine

HO H

HO N H H3CO H

N H

H3CO

N Quinine

N Quinidine

Me

N Me

OH

CH2OH

tropine (-) hyoscyamine

Me
N

CH2OH

(-) hyoscine (scopolamine)

O N H

pelletierine

EFEK FARMAKOLOGI ALKALOID

1.

Analgetik dan narkotik : morfin 2. Alkaloid jantung : alkaloid kinidin dan spartein (Erytropleum guineense) 3. alkaloid yg mempengaruhi peredaran darah dan pernafasan : Veratrum, Rauwolfia (hipotensi), lobelia (lobelin murni obat asma) 4. kemoterapetik dan antiparasit (kina, areca dan granatum (anticacing),

 5.

stimulan uterus : secale alkaloid (Hydrastis), alkaloid benzilisokinolin (berberis) 6. anastetik lokal (cocain) 7. midriatika : belladona dan alkaloid coca.

AlkaloidTropan

Ester alkaloid : asam organik + amino alcohol (Basa). The parent base is the Tropane base.
H N
1 7 6 5 4 3 2

NH

Alkaloid Tropane dikelompokan mjd: 1- Solanaceous Tropane Alkaloids. 2- Erythroxylon (Coca) Alkaloids.

1- Solanaceous Tropane Alkaloids

Terdapat:
Atropa, Datura, Hyoscyamus, Duboisia spp.

Alkaloid

utama:

1- Atropine. 2- Hyoscyamine. 3. Hyoscine (Scopolamine).

Atropine & Hypscyamine

Hyoscyamine is the major natural alkaloid with negative optical rotation (l- form). During extraction hyoscyamine racemizes to the optically inactive dl Atropine. Both alkaloids composed of tropine base and tropic acid.
Tropic Acid
Me N H O CH2OH Me N CH2OH O O O Atropine

NCH3

O
*

Tropine base

OH
(-)-Hyoscyamine

Hyoscine (Scopolamine)

Hyoscine is an ester of l-tropic acid with scopoline base. Hyoscine is a syrupy liquid.
Tropic Acid O NCH3 O

Scopoline base

OH

 Khasiat dan aksi farmakologi:

The three Alkaloids are anticholinergic agents:

Decrease saliva and GIT secretions so used preoperative. Decrease motility of smooth muscles so used as antispasmodics. Stimulate respiratory system. A mydriatic (causes dilatation of the eye pupil).

An antidote to organophosphorus insecticides.

Hyoscine has more central effect so it is sedative and hypnotic. Hyoscine is mainly used as antiemetic.

2- Erythroxylon (Coca) Alkaloids

Occurrence:
Coca leaves contain about 2% total alkaloids.

Main

Alkaloids are:
N H3C

O C OH OH

1- Cocaine. 2- Cinnamylcocaine. 3. a- truxilline.

Ecogonine

The base for Coca Alakloid is called Ecogonine

Cocaine

It is the major Alkaloid in Coca leaves. Cocaine is diester Alkaloid. Heating at 160 0C in conc. HCl leads to hydrolyses of cacaine to MeOH, Benzoic acid and Ecogonine base.
COOMe NCH3 O

Benzoic acid

Ecgonine base O

Production of Cocaine commercially:

The total Alkaloids are hydrolysed to obtain the free base. The base is then Methylated with HCl in MeOH. The Methylated base is then esterified with Benzoly chloride.

Cinnamylcocaine
COOMe NCH3 O Cinnamic acid O

Ecgonine base

 Uses:

Cocaine was used as local anesthetic. Cocaine has a CNS stimulant activity so is one of the widely abused drugs.

Catharanthus :Vinca
Catharanthus

roseus Family : Apocynaceae

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 Perennial

or annual herbaceous plant

40-60cm . The leaves have acute base , rounded apex and have entire margin . The flowers are rose or violet or white or white with red eyes . The fruits have slight odour with bitter taste . The leaves have very strong and unpleasant odour and taste. origin : Australia, Madagascar also cultivated in Tropical Africa .
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Biochemical constituents

Alkaloid indole group : 1. Vincristine 2. Vinblastine 3. Vindoline (inert) 4. Catharanthine (inert)

500kg of Catharanthus plant used to isolate 1g vincristine
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Therapeutic uses
Anti-neoplastic

activity

(anti tumer) Used for treatment of leukemia in children.

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Medications
Vincristine -Vials- Abic 2. Oncovin - Vincristine Vials-Lily 3. Velbe -Vinblastine Vials-Lily (Hodgkins disease ) 4. Blastovine -Vinblastine-Teva Vials. All of these drugs present as sulphate salts.
1.
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