Ecgonidine

Ecgonidine

Names
IUPAC name 8-Methyl-8-azabicyclo[3.2.1]oct-3-ene-4-carboxylic acid
Other names Anhydroecgonine
Identifiers
CAS Number	484-93-5
ChemSpider	16735787
Jmol interactive 3D	Image Image
PubChem	101709
InChI 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 Key: ZAZOGAHQAWUCJK-IYSWYEEDSA-N 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
SMILES CN1C2CCC1C(=CC2)C(=O)O OC(=O)\C2=C\C[C@@H]1CC[C@H]2N1
Properties
Chemical formula	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

References

1. 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.
2. 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.