Chembox new
Name = Ecgonine
ImageFile = Ecgonin - Ecgonine.svg
ImageName = Semi-skeletal formula of ecgonine
ImageFile1 = Ecgonine-3D-balls.png ImageName1 = Ball-and-stick model of the ecgonine molecule
IUPACName = 3-hydroxy-8-methyl-8-azabicyclo [3.2.1] octane-2-carboxylic acid
Section1 = Chembox Identifiers
CASNo = 481-37-8

Section2 = Chembox Properties
Formula = C9H15NO3
MolarMass = 185.2203 g/mol
Density = 1.293 ± 0.06 g/cm³
MeltingPt =
BoilingPt =

Ecgonine is an organic chemical and tropane alkaloid found naturally in coca leaves. It is has a close structural relation to cocaine: it is both a metabolite and a , 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.

ee also




Wikimedia Foundation. 2010.

Look at other dictionaries:

  • Ecgonine — Général Nom IUPAC aci …   Wikipédia en Français

  • Ecgonine — Ec go*nine (?; 104), n. [Gr. e kgonos sprung from.] (Chem.) A colorless, crystalline, nitrogenous base, obtained by the decomposition of cocaine. [1913 Webster] || …   The Collaborative International Dictionary of English

  • ecgonine — noun An organic chemical and tropane alkaloid found naturally in coca leaves …   Wiktionary

  • ecgonine — The important part of the cocaine molecule; a topical anesthetic; basis of many coca alkaloids. e. benzoate SYN: benzoylecgonine. * * * ec·go·nine ek gə .nēn, nən n a crystalline alkaloid C9H15NO3 obtained by hydrolysis o …   Medical dictionary

  • ecgonine — ec·go·nine …   English syllables

  • ecgonine — ˈekgəˌnēn, nə̇n noun ( s) Etymology: International Scientific Vocabulary ecgon (from Greek ekgonos born of, sprung from, from ek out of, out + gonos child) + ine; akin to Greek gignesthai to be born more at kin : a crystalline alkaloid C9H15 …   Useful english dictionary

  • ecgonine methyl ester — the major hydrolytic metabolite of cocaine detectable in blood by laboratory testing, accounting for approximately 49 per cent of cocaine metabolism …   Medical dictionary

  • 481-37-8 — Ecgonine Ecgonine Général Nom IUPAC …   Wikipédia en Français

  • Controlled Substances Act — Acronym CSA Enacted by the 91st United States Congress Effective October 27, 1970 Citations Public La …   Wikipedia

  • Cocaine — For other uses, see Cocaine (disambiguation). Cocaine …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”

We are using cookies for the best presentation of our site. Continuing to use this site, you agree with this.