MEDICINAL CHEMISTRY

SEMINAR
Satyam Sachan
18BPH1042
TOPIC- Synthesis of Phenylephrine and Salbutamol
 INTRODUCTION
• These two drugs (Salbutamol and Phenylephrine) acts on autonomic
nervous system which is responsible for control of the bodily functions
which are not consciously directed such as breathing, heartbeat and
digestive processes.
• Phenylephrine: - Phenylephrine is a selective Alpha-1 adrenergic
receptor agonist
• It belongs to phenethylamine class.
SYNTHESIS OF PHENYLEPHRINE
 SYNTHESIS
• Synthesis of phenylephrine starts with Chloro Acetyl Phenol.
• When this reaction starts with methylamine then, this chloride group gets
replaced and this methylamine is attached forming the intermediate.
• Now catalytic reduction takes place.
• In catalytic reduction this keto group will get reduced and form the alcoholic or
OH group.
• Mechanism of action- Oral phenylephrine is extensively metabolized by
monoamine oxidase which is an enzyme prese3nt on the mitochondrial
membrane of cells throughout the body.
• Phenylephrine is a sympathomimetic drug which mimics the action of
epinephrine, hence it selectively binds to Alpha-1 receptors which cause blood
vessels to constrict.
 USES AND SIDE EFFECTS
• Uses: Nasal decongestant, pupil dilation vasopressor
• Side effects: High B.P, prostatic hyperplasia, rhinitis medimentosa
• Dose: 10% ophthalmic, 1% for IM and IV.
 SALBUTAMOL
• Salbutamol is a selective Beta-2 agonist.
 SYNTHESIS OF SALBUTAMOL
• Synthesis starts with Alpha hydroxy benzyl alcohol.
• When it reacts with chloro acetyl chloride
• Then the bond shifts towards chloride because it has higher
electronegativity and develops slightly negative charge and this carbon
has slightly (+) charge.
• Now when chloride gets removed then this acetyl chloride group gets
attached to the benzene ring.
• Formation of intermediate takes place.
• Now this intermediate is reduced via MPV reduction
• Now, this keto group is reduced to form the alcohol forming salbutamol.
 MECHANISM OF ACTION
• The tertiary butyl group in salbutamol makes it selective for Beta-2
receptors, which are the predominant receptors on the bronchial smooth
muscles.
• Uses: Salbutamol is typically used to treat bronchospasm, intravenous
salbutamol can be used as tocolytic to relax the uterine smooth muscle to
delay premature labor.
Thank You