this is the s;liode of cocain alkaloid which is obtain from leaves of erythroxylon coca

2. Aditya R.Bhatkar
seigler@life.illinois.edu
http://www.life.illinois.edu/seigler

3. Introduction
 The use of medicinal plants is found in almost all
cultures. In some, many types of plants are used.
Some are efficacious and others are not.
 The science of botany originated in the study of
medicinal plants. Chemistry, botany, and
medicine were all considered one field until the
1700's.

4. Coca Leaves

5. Synonyms
 2β-Carbomethoxy-3β-benzoxytropane;
 Cocaine
 β-Cocaine
 Benzoylmethylecgonine
 Ecgonine methyl ester benzoate.

6. Biological Source
It is obtained from the leaves
of Erythroxylon coca Lam. and other
species of Erythroxylon,
(Erythroxylaceae); and leaves
of Erythroxylon truxillense Rusby
(Erythroxylaceae).
Biological Source

8. Cultivation
1. Coca plant is grown similarly to tea-plantation. Seeds are
sown in rich, light and well drained soil at an altitude of
500-2000 meters.
2. It requires a humid atmosphere, rainfall not below 75- 80
inch and temperature between 59-68°F. It thrives best in
well drained moist loams rich in humus. The plant can be
propagated by cuttings, but for raising plantations,
seedlings are raised in nurseries and transplanted. The first
crop of leaves is gathered in 1-3 years after planting. Only
the stiff ripe leaves, easily detached, are collected. The
young leaves are reported to be rich in cinnamylcocaine
and this is replaced in the old leaves by cocaine or
truxilline.

9. Chemical Structure

10. Coca and cocaine
 The Indians of Andean South America have long
used coca leaves (from Erythroxylum coca,
Erythroxylaceae) as a stimulant. The Indians
chewed the leaves mixed with lime to free the
alkaloids. The alkaloids reduced feelings of
hunger and pain.
 Later when the alkaloids were isolated, it was
discovered that they had local anesthetic
properties. Cocaine has been used for surgery
(especially dental surgery).

11. Isolation Of Cocain
1. Extracted from the plant by digestion either with
sodium carbonate solution or with lime water and
by subsequent solvent extraction using petroleum
ether (bp 160-180°C; or 200-220°C).
2. The combined petroleum ether extract is shaken
up with dilute HCl.
3. The solution of hydrochloride thus obtained is
concentrated carefully in a thin-film evaporator.
4. In case, the leaves are rich in cocaine content, as
in the Peruvian coca leaves, a major portion of
cocaine gets separated as crystals.

12. Coca, Erythroxylum coca,
Erythroxylaceae

13. 1. Huanaco or Bolivian Coca leaves are entire,
3-8 cm long. 1.5-4 cm wide, shortly
petiolated, apex-acute, base tapering,
lamina-brown and glabrous, margin entire,
midrib prominent on the lower surface with
a ridge on its upper surface, apex acute,
surface-glabrous, slightly glossy, texture
thin, odor-distinct, taste-bitter.
2. Truxillo or Peruvian coca are more or less
broken, pale green in color, lamina is 1.6-6
cm long, shape elliptical, margin entire,
venation is identical but ridges on lower
surface are conspicuous, apex acute, base
tapering, surface-glabrous, not glossy,
texture-thin, fragile; odor is distinct and
taste is bitter.

16. Collection of Coca Paste

17. Chemical constituent

18. Chemical constituent
1. The pharmacologically active ingredient of coca is the cocaine
alkaloid, which is found in the amount of about 0.3 to 1.5%
2. the coca leaf contains a number of other alkaloids,
including methyl ecgonine cinnamate,
benzoylecgonine, truxilline, hydroxytropacocaine, tropacocain
e, ecgonine, cuscohygrine, dihydrocuscohygrine, nicotine,
and hygrine
3. raw leaf is consumed in tea, between 59 and 90% of the coca
alkaloid
4. coca plant contains essential minerals (calcium, potassium,
phosphorus), vitamins (B1, B2, C, and E) and nutrients such as
protein and fiber.

19. 5. Coca leaves contain 0.7-1.5% of alkaloids which are
of three type derivatives of:
a. ecgonine (cocaine, cinnamylcocaine , a and ß
truxilline
b. tropine (tropococaine, valerine) and
c.hygrine (hygrolline, cuscohygrine)
The alkaloidal composition varies according to the
variety of the plant and stage of development of
leaves.
Cocaine, cinnamylcocaine and a truxllline are the
most important alkaloids.
The constituents isolated from the leaves are simple
alkaloids (hygrine, dihydrocuscohygrine,
tropococaine, four yellow crystalline glycosides.
cocatannic acid and essential oil.

20. 6. ocaine is the methyl ester of benzoylecgonine.
7. On hydrolysis it yields ecgonine ,benzoic acid and
methyl alcohol.
8. Cinnamyl-cocaine on hydrolysis gives ecgonine, methyl
alcohol and cinnamic acid, while a truxilline forms
ecgonine, methyl alcohol and a truxillic acid
9. Besides the alkaloids, coca leaves contain an essential
oil [O.O6 - 0.13%), the chief constituent of which is
methyl salicylate. A coloring matter, coca citrin has
been reported from the leaves.

21. Uses
1. Coca leaves are stimulant and astringent.
2. They are used in masticators.
3. Cocaine is local anesthetic and has stimulant action on C.N.S,
and used in dental anesthesia and minor local surgery of
ophthalmic, ear, nose and throat.
4. Some of these non-psychoactive chemicals are still used for
the flavoring of Coca-Cola. When chewed, Coca acts as a
stimulant to help suppress hunger sensations, thirst, and
fatigue.

22. 5. Chewing coca leaves with a dash of powdered lime is a
nutritious and energizing way to induce healthy mood
without causing an unsustainable high.

23. Identification Test
1. Cocaine Permanganate: The addition of a drop of
saturated solution of KMnO4 to a solution of cocaine
prepared in a saturated solution of alum gives rise to a violet
crystalline precipitate due to the formation of cocaine
permanganate. It clearly shows characteristic violet
aggregates of plates when examined under the microscope.
2. Cocaine Hydrochloride (C17H21NO4.HCl) (Cocaine
Muriate): It is obtained as granules, crystals, or powder. It
has a slightly bitter taste and usually numbs lips and tongue.
Its physical characteristics are: mp ~ 195°C; [α]D – 72° (C = 2
in aqueous solution); 1 g dissolves in 0.4 ml of water; 3.2 ml
cold and 2 ml hot alcohol; 12.5 ml chloroform. It is also
soluble in glycerol and acetone; and insoluble in ether or oils.

24. 3. Cocaine Nitrate Dihydrate (C17H22N2O7.2H2O): Its crystals
have mp 58-63°C. It is freely soluble in water or ethanol; and
slightly soluble in ether.
4. Cocaine Sulphate (C17H21NO4.H2SO4): It is obtained as white,
crystalline or granular powder, which is soluble in ethanol and
water.