Chemistry:Ecgonidine
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| IUPAC name
Trop-2-ene-2-carboxylic acid
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| Systematic IUPAC name
(1R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acid | |
| Other names
Anhydroecgonine
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C9H13NO2 | |
| Molar mass | 167.205 g·mol−1 |
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 | |
Ecgonidine (anhydroecgonine) is an alkaloid related to ecgonine and cocaine. It has a structure with a cycloheptene ring, with a nitrogen bridge, and a carboxylic acid side chain.
Methylecgonidine is produced by pyrolysis in the process of smoking crack cocaine, and then subsequently metabolised to ecgonidine, and so these two compounds can be tested for as a specific biomarker for crack cocaine use.[1] Ecgonidine is formed as a metabolite of methylecgonidine, and so the relative concentrations of the two compounds can be used to gauge how recently crack cocaine was smoked. If levels of methylecgonidine are higher, then the drug was smoked recently; however after a longer time period mainly ecgonidine will be present.[2] Ecgonidine has a half-life in the body of around 94–137 minutes, and so can be used to detect use of crack cocaine up to 8–10 hours after the drug is consumed.
See also
- Coca alkaloids
- Ecgonine
- Tropacocaine
References
- ↑ "Stability of methylecgonidine and ecgonidine in sheep plasma in vitro". Clinical Chemistry 46 (11): 1787–95. November 2000. doi:10.1093/clinchem/46.11.1787. PMID 11067814.
- ↑ "Electron ionization mass fragmentometric detection of urinary ecgonidine, a hydrolytic product of methylecgonidine, as an indicator of smoking cocaine". Journal of Mass Spectrometry 34 (6): 651–60. June 1999. doi:10.1002/(SICI)1096-9888(199906)34:6<651::AID-JMS817>3.0.CO;2-M. PMID 10394630. Bibcode: 1999JMSp...34..651P.
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