Ecgonidine

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.

Ecgonidine
Names
IUPAC name
Trop-2-ene-2-carboxylic acid
Systematic IUPAC name
(1R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acid
Other names
Anhydroecgonine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.919
UNII
  • InChI=1S/C8H11NO2/c10-8(11)6-3-1-5-2-4-7(6)9-5/h3,5,7,9H,1-2,4H2,(H,10,11)/t5-,7-/m1/s1 checkY
    Key: ZAZOGAHQAWUCJK-IYSWYEEDSA-N checkY
  • InChI=1/C8H11NO2/c10-8(11)6-3-1-5-2-4-7(6)9-5/h3,5,7,9H,1-2,4H2,(H,10,11)/t5-,7-/m1/s1
    Key: ZAZOGAHQAWUCJK-IYSWYEEDBT
  • CN1C2CCC1C(=CC2)C(=O)O
  • OC(=O)\C2=C\C[C@@H]1CC[C@H]2N1
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

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

References
  1. Scheidweiler KB, Shojaie J, Plessinger MA, Wood RW, Kwong TC (November 2000). "Stability of methylecgonidine and ecgonidine in sheep plasma in vitro". Clinical Chemistry. 46 (11): 1787–95. doi:10.1093/clinchem/46.11.1787. PMID 11067814.
  2. Paul BD, McWhorter LK, Smith ML (June 1999). "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. Bibcode:1999JMSp...34..651P. doi:10.1002/(SICI)1096-9888(199906)34:6<651::AID-JMS817>3.0.CO;2-M. PMID 10394630.
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