scopine

tropane

tropane

•scopine

+

+

+

Simple indole alkaloid

donaxine Prodrug

tryptamin

donaxine

Pyrolo-indole alkaloids

+ =

PHYSOSTIGMINE ( ESERINE )

" -Strychnos nux vomica"

N

N

OO

R

R

R= H StrychnineR= OCH3 Brucine

Classification of Ergot Alkaloids:

A- Clavine Type Alkaloids:Simple water soluble bases with little medicinal value. All end with “clavine: e.g. Agroclavine.

B- Lysergic acid Amides:They are all derivatives of (l)-Lysergic acid and subclassified into:1- Simple lysergic acid amides:Composed of Lysergic acid and simple amines.

2- Polypeptide Alkaloids:

Composed of Lysergic acid and at least 3 amino acids.

General Characters: Ergot alkaloids are N-monosubstituted amide derivatives of

both lysergic acid and its isomer isolysergic acid that differ only in configuration at C-8.

On treatment with ammonia lysergic and isolysergic acids give the corresponding amides ergine and isoergine respectively.

Members related to lysergic acid (e.g. ergotamine and ergometrine) are levorotatory, more active and designated by suffix “ine”.

Members related to isolysergic acid (e.g. ergotaminine and ergometrinine), are dextrorotatory, less active and designated by suffix “inine”.

F

NH

N CH3

COOH

10

8

NH

N CH3

COOH

NH

N CH3

CONH2

Lysergic acid Isolysergic acid Ergine

tryptaminISOPRENE

Simple Lysergic acid amides

Ergometrine

Ergonovine

(l - ) lysergic acid and 2 - aminopropanol

NH

N CH3

COHNHCH2C

10

8

CH3OH

Ergonovine (l) (Ergometrine)Ergonovinine (d) (Ergometrinine)

==

Simple Lysergic acid amidesLysergic acid diethylamide (LSD)

NH

N CH3

CON

10

8

C2H5

C2H5

polypeptide alkaloidsa-Hydroxyalanine

ProlinePhenylalanine

Vinca Alkaloids

N

N

R

COOCH3OH

H3COOC

N

NH

H3COOC HOR=CH3 VinblastineR=CHO Vincristine

• Tests for identification:

1-Vanillin /HCl reagent gives with:Vinblastine a pink color. Vincristine an orange-

yellow 2-Van-Urk's reagent: PDAP+H2SO4+FeCl3

→ Reddish-brown color.

Yohimban Alkaloids

Reserpine diester

Imidazole alkaloids

Imidazole

Xanthine(Purine) Alkaloids

Steroidal alkaloids

Terpenoid alkaloids

• e.g.• Alkaloids of Aconitum, • Delphinium and • Taxus

ACONITINEditerpene

Paclitaxel :Taxol

Piperidine[

Pyrrolizidine Alkaloidsderived from the amino acid ornithine

• suffix " necine

Quinolizidine Alkaloids • ( Lupin Alkaloids)

lysine derived

INdolidizine Alkaloids

Quinolinealkaloids

pyrroloquinoline

Camptothecin(CPT,)

(CPT,)

alkaloids Isoquinoline

Ipecacuahna alkaloids

derived from

Tyrosine

FeCl3

Codeine

Berberine