Ecgonine

Structural formula
General
Surname	Ecgonine
other names	(1 R , 2 R , 3 S , 5 S ) -3-Hydroxy-8-methyl-8-azabicyclo [3.2.1] octane-2-carboxylic acid ( IUPAC )
Molecular formula	C 9 H 15 NO 3
External identifiers / databases
EC number	207-565-4
ECHA InfoCard	100.006.879
PubChem	91460
ChemSpider	82586
DrugBank	DB01525
Wikidata	Q420028
properties
Molar mass	185.22 g mol −1
Physical state	firmly
Melting point	205 ° C (monohydrate)
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ecgonine is a tropane alkaloid and is found naturally in the leaves of the coca bush .

Coca plant near La Cumbre, Colombia Erythroxylum coca

Structurally, ecgonine is a cycloheptane derivative with a nitrogen bridge. It is obtained by acid or base catalyzed hydrolysis of cocaine and crystallizes with one molecule of water. The crystals melt at 205 ° C. It is not addictive compared to cocaine.

It is a tertiary base that contains both an acid and an alcohol function in the molecule. Ecgonine is the corresponding carboxylic acid to pseudotropine (equatorial position of the hydroxyl group in position 3). Treatment with phosphorus pentachloride produces anhydroecgonine , C ₉ H ₁₃ NO ₂ , which, when heated to 280 ° C with hydrochloric acid, eliminates carbon dioxide and converts to tropidine , C ₈ H ₁₃ N.

Individual evidence

↑ ^a ^b entry on ecgonine. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich, 2006, p. 245, ISBN 978-3-906390-29-1 .

literature

Hermann Ammon (ed.), Curt Hunnius: Pharmaceutical dictionary. 9th edition. de Gruyter, 2004, ISBN 978-3-11-017475-5 .
Entry on ecgonine. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.

[Roempp-1] try on ecgonine. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Gossauer-3] Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich, 2006, p. 245, ISBN 978-3-906390-29-1 .