Page 69 - phytochemistry general program

1- Tropane alkaloids: cocaine, cinnamyl cocaine, & truxillines and
tropacocaine.

2- Pyrrolidine alkaloids: hygrine and cuscohygrine.

Tropane coca alkaloids

Tropane coca alkaloids are obtained from the leaves and shrubs of family
Erythroxylaceae; namely Erythroxylon coca (Bolivian or Huanuco) and
Erythroxylon truxillense (Peruvian or Truxillo) cultivated in Peru, Bolivia and

Colombia.

Coca leaves contain about 0.7 to 2% of total alkaloids of which cocaine,
cinnamyl cocaine and α-truxilline are the most important. They occur in different
proportions in different commercial varieties. Javanese leaves are usually the
richest in total alkaloids, of which the chief is cinnamyl cocaine; while the Bolivian,
Peruvian and Ceylon leaves contain less total alkaloids but a higher proportion of

cocaine.

Coca alkaloids are di-esters of ecgonine base.

Ecgonine

Me

NH
COOH

OH

H
Ecgonine

Ecgonine is pseudotropine 2-carboxylic acid. It contains four asymmetric
carbon atoms consequently a number of optically active stereoisomeric forms are

possible.

Ecgonine is obtained by hydrolysis of cocaine with alkali or with HCl at
160oC.

Alkaloids from ecgonine base:
Cocaine .1

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