Atropine

C17H23NO3
Structure
Introduction
Naturally occuring tropane alkaloid
Extracted from deadly nightsade and other
plants of family Solanaceae
Serve as a drug with a wide variety of effects
 Natural sources

Atropa belladonna Datura stramonium Mandragora

(Deadly nightshade ) (Jimson weed) officinarum
(Mandrake )
History
In 1831, the pharmacist Mein succeeded the
pure crystalline isolation of atropine.
 The substance was first synthesized by
German chemist Richard Willstatter in
1901.
 Synthesis

Tropine + tropic acid →Atropine

C₈H₁₅NO + C₉H₁₀O₃ → C17H23NO3 + H2O

 Properties of atropine:

Formula : C17H23NO3
Molar mass : 289.369g/mol
Duration of action: 30-60 min.
Onset of action: 1 min
Type : Small molecule
Properties
•Solubility: Low solubility in water 1 gram
•Physical state: white crystals or white
crystalline powder, odorless and has a sharp
bitter taste
•Melting point : 114o C - 119o C
•Boiling point: 393o C
Properties
Absorption: Absorbed from gut, parental sites
and mucous membranes
widely distributed in body
Metabolism takes place in liver
60% excretes unchanged in urine and its effects
disappear quickly within 2 hours except eye
 Physiological effects of atropine:
Parasympatholytic agent
Pesticide poisoning
Treat bracardia
As Mydriatic
Inhibition of salivary and mucus glands
Physiological effects of atropine:

As stimulant of madullar centers

As blocking agent
Treat Allergic rhinitis
Used in the treatment of Asthma in past
Physiological effects of atropine:

Used to treat Spasms (painful involuntary

muscular contractions):
Used as general Anesthesia:
It can be used in the treatment of the
childhood bed wetting and head colds by
drying up nasal and lachrymal secretion.
Side effects - overdose;

Decrease in mucociliary clearance may dry

the mucous membrane of the respiratory
tract resulting mucous plugs
Dryness of mouth
Blurred vision
Attack of glaucoma
 Side effects - overdose;
Constipation
Tachycardia
Collapse of circulatory and respiratory
systems
Urine retention
Headache, confusion, and dizziness
Side effects - overdose;

Nausea, vomiting, restlessness, and

hallucinations
Increase heart rate