Ecgonine

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 in many jurisdictions, as are some substances which can be used as precursors to ecgonine itself.

Ecgonine
Semi-skeletal formula of ecgonine
Ball-and-stick model of the ecgonine molecule
Names
IUPAC name
3β-Hydroxytropane-2β-carboxylic acid
Systematic IUPAC name
(1R,2R,3S,5S)-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.879
EC Number
  • 207-565-4
KEGG
UNII
  • InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5-,6+,7-,8+/m0/s1 ☒N
    Key: PHMBVCPLDPDESM-FKSUSPILSA-N ☒N
  • InChI=1/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5-,6+,7-,8+/m0/s1
    Key: PHMBVCPLDPDESM-FKSUSPILBM
  • O=C(O)[C@H]1[C@@H](O)C[C@H]2N(C)[C@@H]1CC2
Properties
C9H15NO3
Molar mass 185.223 g·mol−1
Density 1.293±0.06 g/cm3
Melting point 198 to 199 °C (388 to 390 °F; 471 to 472 K) (hydrate)
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[1]

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.[1]

See also

References
  1. Chisholm 1911.
  • This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Ecgonine". Encyclopædia Britannica. Vol. 8 (11th ed.). Cambridge University Press. p. 870.
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