Quinolizidine: Alkaloids Alkaloidal Amines Purine Alkaloids
Quinolizidine: Alkaloids Alkaloidal Amines Purine Alkaloids
Quinolizidine: Alkaloids Alkaloidal Amines Purine Alkaloids
Department of pharmacy
Quinolizidine alkaloids
Alkaloidal amines
Purine alkaloids
Pharmacognosy-Lecture 5
Assistant Lecturer Marwan I. Al-Zuhairi / M.Sc.
Quinolizidine-Lupinane alkaloids
• Lupinane contains a methyl group at the quinolizidine
ring.
• These alkaloids of this group are found in scoparius
(broom tops) of cytisus scoparius .
• The alkaloids of this group are Lupinine, and Sparteine
and they are known to be toxic alkaloids.
• Those are biosynthesized by 2 lysine molecules.
• Sparteine is the most important alkaloid, it’s a bitter
viscous liquid alkaloid it can be used to induce uterine
muscles due to its oxytocic action.
• The usual dose to induce labor is 75 mg IM.
Alkaloidal amines
Proto-Alkaloids (Atypical alkaloids)
• The alkaloids in this group do not contain heterocyclic nitrogen atoms, the nitrogen
is not a part of the heterocyclic ring, so it is called atypical alkaloids.
• Many are simple derivatives of phenylalanine & tyrosine; Other alkaloidal amines
are biosynthesized from tryptophan.
• Drugs containing alkaloidal amines:
1) Ephedra which contains Ephedrine
2) Colchicum which contains Colchicine.
3) Khat which contains Cathinone. ( Leaves)
4) Peyote which contains Mescaline. (Tops)
1. Ephedra:
• It is the entire plant or the over ground portion of Ephedra sinica F:
Gentaceae.
• The main alkaloids isolated from the various Ephedra species are
Ephedrine & Pseudoephedrine which are stereo-isomers.
• Ephedrine exhibits optical isomerism since it has two chiral centers,
giving rise to four stereoisomers.
• The pair of enantiomers with the stereochemistry (1R,2S) and
(1S,2R) is designated ephedrine, while the pair of enantiomers with
the stereochemistry (1R,2R) and (1S,2S) is called pseudoephedrine
• Pseudoephedrine can be formed by boiling Ephedrine with 25% HCL.
Production of Ephedrine
• Natural: Ephedrine is produced commercially either by extraction of plant
material or by chemical procedure.
• From the seeds and corm of the plant Colchicum autumnal F: Liliaceae.
• Colchicum contains the alkaloid Colchicine up to 0.8% in the seeds &
0.6% the corm.
• The biosynthesis precursor is phenylalanine in addition to tyrosine.
• The tropolone ring is formed by inclusion of a carbonyl group in the
six-member ring.
• Colchicine lacks basicity and does not form a well-defined series of
salts as do other alkaloids.
• It is used in gout to increase the excretion of uric acid.
• It also causes doubling of chromosomes prevents formation of
microtubules affecting mitosis thus, causing certain mutations in some
types of tumors., experiments show that injection of colchicine will
Inhibit the growth of certain tumors.
3. Khat:
• It is the fresh leaves of Catha edulis F: Celastraceae. The plant is a small
tree or shrub.
• It is cultivated extensively in the Ethiopian highlands (Africa) and in
Yemen, Fresh leaves are regularly transported by air to areas distant
from the centers of cultivation.
• The Expert Committee of Addiction-producing Drugs of the WHO does
not classify khat as a to cause serious addiction however , it is
considered as a drug of abuse that can cause psychological dependence.,
but the French government considers it as an addictive drug.
• The leaves are chewed habitually by many people to alleviate the
sensation of hunger & fatigue which is like that of coca leaves causing
the stimulatory effect of cocaine. Cathinone
• Khat contains a potent phenyl alkyl amine alkaloid called (-)-cathinone.
It has pharmacological properties analogous to those of (+)-
amphetamine with similar potency and mechanism of action by the
induction of catecholamine release from the storage sites.
• Cathinone is stimulant that causes excitement , loss of appetite and
euphoria. Amphetamine
Fresh vs. Dry khat leaves
• The young fresh leaves that come from the tips of the
branches contain the optimum mount of cathinone. In older
leaves, it is converted to the weakly active compounds
cathine which has weaker activity.
Cathinone Cathine
4. Peyote:
• It consists of the dried tops of Lophophora williamsii F: Cactaceae. This plant has
been associated with Indian ceremonies for many years.
• Peyote main action to disturb normal mental function & causes concomitant
hallucination & euphoria.
• The drug contains several alkaloids, the most important one is mescaline,
• Mescaline (3,4,5-trimethoxy phenylethylamine) is regarded as the first of a series
of hallucinogens or psychotomimetic.
Purine bases
Pseudoalkaloids
• Pseudoalkaloids have nitrogen in a heterocyclic ring however not derived from an
amino acid.
• The purines are derivatives of a heterocyclic nucleus consisting of the 6-membered
pyrimidine ring fused to the 5-membered imidazole ring.
• The pharmaceutically important bases of this group are the methylated derivatives
of 2,6-dioxypurine (Xanthine: di-keto purine)
Xanthine
Purine
Purine bases
• Cola (Kola)
• Coffee
• Tea
• Cacao
Uses of purine bases:
THE END