Ecgonine

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Ecgonine
IUPAC name

(1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo [3.2.1]octane-2-carboxylic acid

Identifiers
CAS number 481-37-8 YesY
PubChem 91460
ChemSpider 82586 N
DrugBank DB01525
Jmol-3D images {{#if:O=C(O)[C@H]1[C@@H](O)C[C@H]2N(C)[C@@H]1CC2|Image 1
Properties
Molecular formula C9H15NO3
Molar mass 185.2203 g·mol−1
Density 1.293 ± 0.06 g·cm−3
Melting point 198–199 °C
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Ecgonine (tropane derivative) is a tropane alkaloid found naturally in coca leaves. It 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

References

    External links

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