CNS stimulant

1. E P H E D R I N E
M A D I S H N I A Z
B S C H E M I S R T Y

2. 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. CHEMIAL STRUCTURE:
• Chemical Formula: C10H15NO
• Molecular Weight: 165.23 grams/mole
• Melting Point: 37-39°C
• Boiling Point: 253-255°C
• Brand names:
1. Akovaz,
2. Corphedra.
• Drug class(es):
1. Decongestants
2. vasopressors
EPHEDRINE

4. IUPAC NAME:
T H E I U PAC N A M E S O F T H E T W O E N A N T I O M E R S A R E
( 1 R , 2 S ) - 2 - M E T H Y L A M I N O - 1 - P H E N Y L P R O PA N - 1 - O L
( 1 S , 2 R ) - 2 - M E T H Y L A M I N O - 1 - P H E N Y L P R O PA N - 1 - O L .
A S Y N O N Y M I S E R Y T H R O - E P H E D R I N E .

5. Ephedrine exhibits optical isomerism
and has two chiral centres, giving rise to four stereoisomers
STRUCTURAL ELLUCIDATION:

6. STRUCTURAL COMPARISON:
Ephedrine is a substituted amphetamine and a
structural methamphetamine analogue.
In the outdated D/L system (+)-ephedrine is
also referred to as L-ephedrine and (−)-
ephedrine as D-ephedrine

7. CHEMISTRY:
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 equisetina
• other Ephedra species.
It is most usually marketed as the hydrochloride or
sulfate salt.

8. APPEARANCE:
• White crystalline powder
• Bitter taste
• Soluble in water
• Very soluble in
alcohol

9. MECHANISM OF ACTION:
• It works mainly by increasing the activity of norepinephrine (noradrenaline)
on adrenergic receptors.
• On the surface of fat and muscle cells there are b-receptors
• B-receptors bind with b-agonists (adrenaline) causing chemical reactions that
produce the chemical messenger C- AMP
• C-AMP activates enzymes which induce lipolysis (fat breakdown) in fat cells and
increase metabolism in muscle cells.
• In supplements containing the ephedrine-caffeine-aspirin mix, ephedrine
enhances b-agonist production.
• Caffeine inhibits the breakdown of C-AMP. Aspirin inhibits the reduction of b-
agonist production.

10. EXTRACTION:

11. SYNTHESIS:
Ephedrine can be synthesized from benzaldehyde in a few different
ways. According to the first, benzaldehyde is condensed with
nitroethane, giving 2-methyl-2-nitro-1-phenylethanol, which is
reduced to 2-methyl-2-amino-1-phenylethanol. The necessary L-
isomer is isolated from the mixture of isomers by crystallization.
Methylation of this gives ephedrine.

12. SYNTHESIS:
The second method consists of the fermentation of glucose by
yeast carboligase in the presence of benzaldehyde, which during
the process turns into phenylacetylcarbinol. This is reduced by
hydrogen in the presence of methylamine to give the desired
ephedrine.

13. BIOSYNTHESIS OF EPHEDRINE:
• Biosynthesis of ephedrine by ephedra begins with L-phenylalanine (Phe).
• Phenylalanine is the initial precursor of ephedrine and pseudoephedrine and catalyzed
by phenylalanine ammonia lyase (PAL)

14. BIOSYNTHESIS OF EPHEDRINE:
• Phenylalanine first forms cinnamoyl-CoA via the enzymes phenylalanine ammonia-lyaseand
acylCoAligase.

15. BIOSYNTHESIS OF EPHEDRINE:
• The cinnamoyl-CoA is then reacted with a hydratase to attach the alcohol functional group.The
productisthenreactedwitha retro-aldolase,formingbenzaldehyde
benzaldehyde
Cinnamoyl-CoA

16. BIOSYNTHESIS OF EPHEDRINE:
• Benzaldehyde undergo dehydrogenase to form benzoic acid. After
undergoing condensationwithpyruvate toform1-phenylpropane-1,2-dione
thisreactioncatalyzed by a ThDP-dependent carboligase .Transamination of
1-Phenylpropane-1,2-dione yieldscathinone.

17. • Thencathinoneisreducedtonorephedrine.Intheend,N-Methylationto
form ephedrine.
BIOSYNTHESIS OF EPHEDRINE:

18. MEDICINAL USES:
Its
chemic
al
propert
ies raise
blood
pressur
e and
heart
rate
and
• It is
also
used
for
allergie
s and
hay
fever;
nasal
congest
ion;

19. USE IN
WEIGHT
LOSS:
• Increases fat loss.
• Maintains muscle mass.
• Prevents the fall of HDL cholesterol during
weight loss.
• Increases insulin sensitivity.
• Reduces lipogenesis (the conversion of
carbohydrates to fat).

20. USED AS BODY
BUILDING AIDS:
• Ephedrine has also been used by
athletes who believe it makes them
stronger or have more energy and
endurance.

21. AS A NUTRITIONAL
SUPPLEMENT:
It not only has thermogenic and lipolytic characteristics
but also used as a nutritional supplement. Users have
lost weight and gained strength in prolonged use of
Ephedrine. It is also called a performance-enhancing
pill as it gives an instant energy boost to athletes upon
taking it.

22. BENEFITS OF MODERN EPHEDRINE USE:
• Maintains levels of HDL cholesterol
• May reduce the risk of cardiovascular disease
• No signs of long term toxicity
• May increase life expectancy in women
• It is used to increase urine flow in people who retain fluids.

23. SIDE EFFECTS:
• Abnormally high blood pressure
• Rapid, irregular heartbeat
• Anxiety
• Dizziness
• Insomnia
• Tremor
• Rapid pulse
• Sweating
• Respiratory difficulties
• Confusion
• Hallucinations
• Delirium
• Convulsions.

24. INDIVIDUAL CASES:
• The New England Journal of medicine links at least
54 deaths to ephedrine
• Since 1994 the FDA has had over 800 reported
cases of side effects from ephedrine. 273 resulted in
death
• Death of NFL player Korey Stringer tied to
ephedrine use.
• Numerous college athlete deaths also linked
• Athletic deaths linked to ephedrine result from rise
in body temperature

25. CONCLUSION:
• Ephedrine should be used intelligently and with caution
• Consult a doctor before starting supplementation

26. THANK YOU