Methylecgonidine

Methylecgonidine (anhydromethylecgonine; anhydroecgonine methyl ester; AEME) is a chemical intermediate derived from ecgonine or cocaine.

"AEME" redirects here. For the Australian Army corps, see Royal Australian Electrical and Mechanical Engineers.
Methylecgonidine
Names
IUPAC name
Methyl trop-2-ene-2β-carboxylate
Systematic IUPAC name
Methyl (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
Other names
Anhydromethylecgonine
Anhydroecgonine methyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.164.719
UNII
  • InChI=1S/C10H15NO2/c1-11-7-3-5-8(10(12)13-2)9(11)6-4-7/h5,7,9H,3-4,6H2,1-2H3/t7-,9+/m0/s1 Y
    Key: MPSNEAHFGOEKBI-IONNQARKSA-N Y
  • InChI=1/C10H15NO2/c1-11-7-3-5-8(10(12)13-2)9(11)6-4-7/h5,7,9H,3-4,6H2,1-2H3/t7-,9+/m0/s1
    Key: MPSNEAHFGOEKBI-IONNQARKBC
  • CN2[C@@H]/1CC[C@@H]2C\C=C\1C(=O)OC
Properties
C10H15NO2
Molar mass 181.235 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Methylecgonidine is a pyrolysis product formed when crack cocaine is smoked, making this substance a useful biomarker to specifically test for use of crack cocaine, as opposed to powder cocaine which does not form methylecgonidine as a metabolite. Methylecgonidine has a relatively short half-life of 18–21 minutes, after which it is metabolised to ecgonidine, meaning that the relative concentrations of the two compounds can be used to estimate how recently crack cocaine has been smoked. Methylecgonidine has been shown to be specifically more harmful to the body than other byproducts of cocaine; for example to the heart, lungs & liver. The toxicity is due to a partial agonist effect at M1 and M3 muscarinic receptors, leading to DNA fragmentation and neuronal death by apoptosis.

AEME is also used in scientific research for the manufacture of phenyltropane analogues such as troparil, dichloropane, iometopane, and CFT. Methylecgonidine could also theoretically be used to produce cocaine and so may be a controlled substance in some countries.

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