Ecgonine

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
CAS Number	481-37-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:4743
ChEMBL	ChEMBL612017
ChemSpider	82586 Y
DrugBank	DB01525 Y
ECHA InfoCard	100.006.879
EC Number	207-565-4
KEGG	C10858
PubChem CID	91460
UNII	DX2E9E17AV N
CompTox Dashboard (EPA)	DTXSID701019899 DTXSID20881252, DTXSID701019899
InChI 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
SMILES O=C(O)[C@H]1[C@@H](O)C[C@H]2N(C)[C@@H]1CC2
Properties
Chemical formula	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	AU: S9 (Prohibited substance) BR: Class F1 (Prohibited narcotics) CA: Schedule I UK: Controlled Drug US: Schedule II
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Ecgonine is a tropane alkaloid (alkaloid derivative of tropane) 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.

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

• Coca alkaloids
• Anhydroecgonine
• Cocaethylene
• Dihydrocuscohygrine
• Methylecgonidine
• Salicylmethylecgonine
• Tropinone
• Troparil

References

• 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.