This document discusses the structural elucidation and stereochemistry of ephedrine and morphine. It provides background on the history and traditional uses of ephedrine. The chemistry, extraction process, and mechanism of action of ephedrine are described. The structural elucidation of ephedrine is explained through determination of molecular formula, identification of functional groups, and degradation studies. Similarly, the structural elucidation of morphine is summarized through identification of molecular formula, detection of unsaturation, identification of functional groups, and degradation studies to reveal the phenanthrene ring structure.

1. GURU JAMBHESHWAR UNIVERSITY OF SCIENCE AND
TECHNOLOGY HISAR (HARYANA)
Structural elucidation and stereochemistry of
ephedrine, morphine
Submitted to:-DR. Sandeep Jain
Submitted by:- BHARAT
Roll no:- 220121210012
(M. Pharmacy 1st semester)
{Pharmaceutical chemistry}

2. EPHEDRINE
(history)
Also known as Ma-Huang .
Ephedra has been used as medicine for over 60,000 years.
Used in Chinese medicine for more than 5,000 years.
 Originally prescribed to treat:
1. Asthma
2. congestion
3. allergies

3.  Chemical Formula: C10H15NO
 Molecular Weight: 165.23 grams/mole
 Class: phenyl ethyl amine alkaloid
 Soluble in water.
 Melting Point: 37-39°C
 Boiling Point: 225°C
 Brand names
 1. Akovaz
 2. Corphedra
 Drug class(es)
 1 Decongestants
 2.Vasopressors
CHEMISTRY

4.  Chemically, it is an alkaloid with a phenethylamine skeleton found in
various plants in the genus Ephedra.
 (family: Ephedraceae)
 Ephedra consists of the dried aerial parts of:
 Ephedra gerardiana,
 Ephedra sinica
 Ephedra equisetinas
 other Ephedra species.
 Ephedrine promotes modest short-term weight loss.
phenethylamine

5.  White crystalline powder
 Bitter taste
 Soluble in water
 Very soluble in alcohol
Appearance:

6. Mechanism of action
 Ephedrine is a direct and indirect sympathomimetic amine. As a direct
effect, ephedrine activates alpha-adrenergic and beta-adrenergic
receptors.
 Ephedrine acts as an agonist of alpha-1, beta-1 and beta-2-adrenergic
receptors.The stimulation of alpha-1-adrenergic receptors causes the
constriction of veins and a rise in blood pressure, the stimulation of
beta-1-adrenergic receptors increases cardiac chronotropy and
inotropy, and the stimulation of beta-2-adrenergic receptors causes
vasodilation and bronchodilation.

7. Powdered plant material
Alkalinize with base
Base extracted with CHCI
Solvent distilled off
Residue dissolved in dilute acid
Decolorizing carbon, filtration
Filtrate alkalinized and alkaloid re-extracted with diethyl ether or similar solvent
Evaporate solvent, recrystallize from hot water
Pure (-)-Ephedrine
EXTRACTION

8. 1. Determination of molecular formula - C10H15NO
2. Presence of secondary amino (-NH-) group.
3. Presence of hydroxyl(-OH) group.
4. .Presence of N-methyl (-N-CH3) group.
5. Presence of benzene nucleus (monosubstituted benzene).
6. Nature of side chain
7. Confirmation of structure by degradation studies
8. .Synthesis
Structure elucidation of Ephedrine

19. 1.Determinationof molecular formula-C17H19O3N
2.Detectionof unsaturation - Presence of double bond.
3.Nature of oxygen - Presence of two –OH grs & ether group
4.Nature of nitrogen atom -Presence of ter. Amino group.
5.Degradationstudies - presence of phenanthrene ring structure
Structure elucidation

22. 4.Nature of nitrogen atom

23. 5.Degradation studies

25. Structure activity relationship (Morphine)

28. Thank you