Ecgonine
IUPAC name	3-hydroxy-8-methyl-8-azabicyclo [3.2.1]octane-2-carboxylic acid
Identifiers
CAS number	[481-37-8]
SMILES	CN2C1CCC2CC(O)C1C(O)=O
Properties
Molecular formula	C9H15NO3
Molar mass	185.2203 g/mol
Density	1.293 ± 0.06 g/cm³
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Ecgonine is an organic chemical and tropane alkaloid found naturally in coca leaves. It is has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance, as are all known substances which can be used as precursors to ecgonine itself.

Structurally, ecgonine is a cycloheptane derivative with a nitrogen bridge. It is obtained by hydrolysis of cocaine with acids or alkalis, and crystallizes with one molecule of water, the crystals melting at 198–199°C. It is levorotary, and on warming with alkalis gives iso-ecgonine, which is dextrorotary.

It is a tertiary base, and has the properties of an acid and an alcohol. 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 280°C with hydrochloric acid, eliminates carbon dioxide and yields tropidine, C₈H₁₃N.

See also

• Cocaine
• Benzoylecgonine
• Truxilline
• Hydroxytropacocaine
• Tropacocaine
• Cuscohygrine
• Dihydrocuscohygrine
• Hygrine
• Cocaethylene
• Anhydroecgonine
• Methylecgonidine
• Troparil

References

• This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.

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Source: adapted by the editor from Wikipedia, the free encyclopedia; from the article "Ecgonine". Image Credit.

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