Ecgonidine

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IUPACName = 8-Methyl-8-azabicyclo [3.2.1] oct-3-ene-4-carboxylic acid
OtherNames = Anhydroecgonine
Section1 = Chembox Identifiers
CASNo = 484-93-5
PubChem = 101709
SMILES = CN1C2CCC1C(=CC2)C(=O)O
Section2 = Chembox Properties
Formula = C₉H₁₃NO₂
MolarMass = 167.205 g/mol
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Ecgonidine (anhydroecgonine) is an alkaloid related to ecgonine and cocaine.

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. [ Scheidweiler KB, Shojaie J, Plessinger MA, Wood RW, Kwong TC. Stability of methylecgonidine and ecgonidine in sheep plasma in vitro. Clinical Chemistry. 2000 Nov;46(11):1787-95.] 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. [ Paul BD, McWhorter LK, Smith ML. Electron ionization mass fragmentometric detection of urinary ecgonidine, a hydrolytic product of methylecgonidine, as an indicator of smoking cocaine. Journal of Mass Spectrometry. 1999 Jun;34(6):651-60.] 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.

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