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Encyclopedia Britannica



ECGONINE

This article appears in Volume V08, Page 870 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: ECG-EMS
ECGONINE , in
chemistry
 , C9H15NO3, a cycloheptane derivative with a nitrogen
bridge
 . It is obtained by hydrolysing cocaine with acids or alkalis, and crystallizes with one molecule of water, the crystals melting at 1980 to 199 C. It is laevo-rotatory, and on warming with alkalis gives iso-ecgonine, which is dextro-rotatory. It is a tertiary base, .and has also the properties of an acid and an
alcohol
 . When boiled with
caustic
  baryta it gives methyl-amine. It is the carboxylic acid corresponding to
tropine
 , for it yields the same products on oxidation, and by treatment with
phosphorus
  pentachloride 'is converted into anhydroecgonine, C9H13NO2, which, when heated to 28o C. with hydrochloric acid, splits out carbon dioxide and yields tropidine, C8H13N. Anhydroecgonine melts at 235 C., and has an acid and a basic
character
 . It is an unsaturated compound, and on oxidation with potassium permanganate gives succinic acid. It is apparently a tropidine monocarboxylic acid, for on exhaustive methylation it yields cycloheptatriene-1.3.5-carboxylic acid-7.
Sodium in amyl
alcohol
  solution reduces it to hydroecgonidine C9H15NO2, while moderate oxidation by potassium permanganate converts it into norecgonine. The presence of the heptamethylene
ring
  in these compounds is shown by the production of suberone by the exhaustive methylation, &c., of hydroecgonidine
ethyl
  ester (see POLYMETHYLENES and
TROPINE
 ). The above compounds may be represented as:
CH;.CHCI H COON CH2CHCH'COOH CH2CHC H'COOH
N'CH3 CH'OH NCH3 (H NCH3 CI H2
CH2CHc1I2 CH2CH---CH CH2CHCH2
Ecgonine Anhydroecgonine Hydroecgonidine


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