Ecgonine

Ecgonine

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
3DMet	B05731
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)	DTXSID20881252
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 (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.

Structurally, ecgonine is a

• 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.