Ecgonidine

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
CAS Number	484-93-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	16735787 ;
ECHA InfoCard	100.006.919
PubChem CID	101709;
UNII	9H2C60Y82I ;
CompTox Dashboard (EPA)	DTXSID00901169 DTXSID60897574, DTXSID00901169 ;
	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). verify (what is ?) 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.

References

^ 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.
^ 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.

[pmid11067814-1] 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.

[pmid10394630-2] 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.

[1]

[2]

See also

References